Men's Fashion: How to rock the blazer and jeans look?
December 4, 2013 11:17 AM   Subscribe

My husband would like to do the blazer and jeans look occasionally so I would like to get him a blazer but I'm not sure whether that will suffice. He only wears non-sneaker shoes when he has to and his sneakers are definitely more athletic style than just casual shoe style. And I'm not sure that his jeans are nice enough to pull off this look. Help?

Husband has mentioned that he would like a blazer or sport coat (are these different things?) for the holidays. He has been interested in doing a blazer and jeans look, probably with a t shirt rather than a collared shirt (behold! inspirational images). He doesn't own many ties and doesn't wear them often at all, ditto non-sneaker shoes. Most of his shirts are plain and he's not trying to be clever so I don't think he's thinking of going with graphic t-shirts under jackets like this.

When he's attempted this look before, I think it looks too haphazard, like if I threw on a blazer on top of yoga pants and a tank top. I've thought of getting him a blazer like this or this but I would like to give it to him with some style guidance. Unfortunately, I don't have a whole lot to offer myself.

For starters, are those jackets appropriate for this type of look? Should I go for a material that is seasonally flexible? Most of my husband's clothes come from Gap or Banana Republic. Is it okay to pair jeans from there (like this) with a blazer like that? He also has several pairs of grey chino-type pants and khakis so he might wear those with a t-shirt and a blazer too.

When I looked for images, it looked like a lot of the men were wearing nice shoes. Does he need to wear nice shoes to do this look? Would it be okay if he were to wear, say, a black blazer, a t-shirt, jeans and athletic sneakers? What if he wore a button-down shirt instead of a t-shirt? Will this whole look work best if he sticks to a dark palette - black blazer, dark shirt, dark jeans?

If he wants to do the blazer, jeans and t-shirt look, does it matter what kind of t-shirt? He has a handful of cute, goofy t-shirts but most of his t-shirts are grey and black crew and v-necks. He has a lot of crappy white undershirts but he wouldn't wear that under the blazer without something on top of it. If he wanted to wear a blazer over a sweater, should he wear a collared shirt under the sweater? He might like that for when it's crazy cold in the winter but not the rest of the time.

What little I know about fashion includes the importance of balance. Is it the kind of thing where, if he wants to wear a blazer, assuming he is also going to wear a shirt, shoes and jeans, two out of the three can be less fancy? Could he do blazer, button down shirt, jeans with holes near the ankles and sneakers? Blazer, t-shirt, nicer jeans, sneakers? Can he scale based on the nice-ness of the situation so maybe, if it's a nicer situation, only one item is kind of crappy? So maybe when he wants to look a little nicer, he could do blazer, button down shirt, nicer jeans or non-jean pants, sneakers? Or blazer, t-shirt, nicer pants, shoes?

Forgive me if I'm over-thinking this, I'm just trying to help him out. I want to get him a blazer but he's not going to wear it if he puts it on and doesn't like how he looks, so if there are things I can get him that would improve the look (a new belt that matches?), I'd be happy to do it. And he's so cute that I want to help him look his best :-) If you have any specific blazer recommendations, that'd be helpful. Thanks!
posted by kat518 to Clothing, Beauty, & Fashion (59 answers total) 10 users marked this as a favorite

I don't know. Farbeit from me to be qualified to give fashion advice, but I think if your husband wants to pull this off, you are going to at least need to 86 the athletic sneakers. they should probably be destroyed regardless of his blazer plans. Also, I think it will take a lot of confidence to pull it off without a collared shirt. The t-shirt+blazer combo screams way too tech startup CEO to me.

That said, if you guys already shop at the Gap, it's not like he's averse to nicer looking clothes. Get him some nicer flat-soled sneakers, some classic oxford shirts, and he could rock the fuck out of a nice dark-blue or black blazer.
posted by Think_Long at 11:24 AM on December 4, 2013 [5 favorites]

Also, one thing to clarify: is your husband going for the handsome Brooklyn loft model type look (like in your example pictures), or the more hip professor look? If it's the latter, you may want to go outside the classic blue/black fabrics and get something with a bit more weave - I don't know the correct vocabulary, but maybe a tweed.
posted by Think_Long at 11:26 AM on December 4, 2013

Would it be okay if he were to wear, say, a black blazer, a t-shirt, jeans and athletic sneakers?

No, absolutely not. This would be an awful look. There are dressier shoes that are just as comfortable as sneakers.

Also, black is a weird color for a blazer. It's tough to pull off outside a funeral, nightclub, or formal event.
posted by jayder at 11:26 AM on December 4, 2013 [4 favorites]

"The t-shirt+blazer combo screams way too tech startup CEO to me."

Funny that you say that. Replace "CEO" with "co-founder" and you basically described his current gig :-) That said, he does not want to look trendy or like he's trying too hard - just like he put in more effort than usual.
posted by kat518 at 11:28 AM on December 4, 2013

When you say "athletic sneakers" do you mean "sneakers made specifically for a sport" or "sneakers in a sporty style that may or may not be used for a sport"? Basically, former should only be worn for the sport or if you don't particularly care about what you're wearing because it is not that sort of situation. If they're fashionable high-tops or something, they generally look the best with skinnier jeans (definitely skinnier than the ones you link.) Otherwise you run the risk of looking like mid-90s Jerry Seinfeld, which is not a good look on anyone.

Also I have no idea how old he is, or what his general style is, but if he's dressing mostly from Gap and Banana Republic, the "stylish hi-tops" thing is going to look a little odd just because street fashion doesn't mix well with that sort of thing. Throw a blazer on top of that and it's a mess.

Otherwise, there's all sorts of casual/fashionable low-key sneakers to pick from, but the important part is that they don't look like shoes you wear for a sport: the soles are low, the design is usually simpler and more toned down, and so on. And they also don't require the sort of skin-tight jeans I end up having to wear with my giant Pumas.
posted by griphus at 11:29 AM on December 4, 2013 [1 favorite]

If you're worried about the "haphazard"-ness that sometimes happens when you cross styles like this, I'd go for a sportcoat rather than a blazer. (yes, they're different!) Sportcoats are more casual, so they could be paired with jeans more easily.

Here is an article on Dappered which outlines the differences between blazers, sport coats, and suit jackets.

Sometimes a t-shirt + blazer is a little to far from each other to pull it off without looking like you're trying too hard. But that doesn't mean you need to go full-on button up. Layering a blazer with other forms of knit tops and jeans works really well, kinda like tshirts but a heavier material that looks more polished.
posted by FirstMateKate at 11:33 AM on December 4, 2013 [3 favorites]

IMO, blazer + t-shirt looks awful, even moreso with sneakers.

What about a nice oxford button down? J.Crew has nice, thin shirts that aren't dressy.

Maybe try some chukka's instead of sneaks?
posted by MisantropicPainforest at 11:34 AM on December 4, 2013

When I looked for images, it looked like a lot of the men were wearing nice shoes. Does he need to wear nice shoes to do this look? Would it be okay if he were to wear, say, a black blazer, a t-shirt, jeans and athletic sneakers? What if he wore a button-down shirt instead of a t-shirt? Will this whole look work best if he sticks to a dark palette - black blazer, dark shirt, dark jeans?

I would avoid black blazers. It seems intuitive that they would look plain, but they don't. Navy is a much better choice. Personally, I think to pull this off you have to do more than just throw the blazer on a t-shirt, jeans, running shoe outfit. If you're super stylish that can look fine, but it's really not a good look for most people. Get a couple button down shirts (oxford cloth button down is the menswear nomenclature) in basic colors (white, blue, pink) to wear under the blazer. Get some casual shoes that aren't sneakers, probably in brown. Now it looks like something you're doing on purpose not like you grabbed the wrong jacket on the way out the door for a run.

That's if you're wedded to the blazer and jeans look. I don't love that look myself, so I don't ever do that, but plenty of people like it and do. As Think_Long suggested you might also want to consider tweeds and other rougher fabrics for the jacket. A casual brown tweed, a sweater over a button down shirt, jeans, and brown shoes(I like suede saddle shoes, but this isn't for everyone) is a look I really like for fall/winter.
posted by Bulgaroktonos at 11:35 AM on December 4, 2013

If not black for a blazer, do you think grey? Charcoal? I hear you, I'm just trying to think of something that will go well with his current wardrobe.

Unfortunately, I'm not sure how much I can do about his shoes. I think his current pair looks like this. When it's been cold, he's worn something like this. For years, he wore something like this [shudder].Shoe shopping with him is kind of awful. He likes Zappos, though and gets their next-day delivery. He's worn Pumas and liked them but he's afraid of being too trendy. He bought a pair of red Pumas and never wore them because they stood out too much.
posted by kat518 at 11:35 AM on December 4, 2013 [1 favorite]

The key thing here is to get a blazer or a sport coat, but not a suit jacket or anything that resembles it. A blazer will usually be navy blue, usually have metal buttons, and ideally have patch pockets. It will usually be a rougher material than a navy suit jacket. A sport coat will also be rougher than a suit jacket -- think tweed or herringbone -- and often have a looser construction.

Something smooth and shiny and constructed will look wrong with jeans. You're definitely on the right track with your ideas about balance, but to look well-composed, there shouldn't be too much distance between the dressiest item and the most casual. Both blazers and sport coats are essentially casual.

(I personally am against the t-shirt and jacket look, but some people can pull it off.)
posted by neroli at 11:37 AM on December 4, 2013

Get him a pair of Converse off Zappos and give them a shot with the outfit. Because those sneakers you linked are exactly the kind you absolutely do not want to wear this the sort of outfit you're describing. At least not if he wants to look well put-together.
posted by griphus at 11:37 AM on December 4, 2013 [28 favorites]

The "blazer and jeans" look works better with a button down in my opinion rather than a t-shirt. The t-shirt looks kind of dated and 90s unless done absolutely perfectly. Maybe OK with exactly the perfect band shirt or something geekily brilliant? But not just any t-shirt and not a plain t-shirt and not any sort of graphic or logo tee that is not exactly perfect.

A tie is not necessary. Blazer, button-down, jeans, and sneakers is just fine.

The jeans and sneakers also require a degree of finesse and style savvy. Jeans should be dark denim and a relatively slim, classic cut. No carpenter jeans. Sneakers should NOT under any circumstances be athletic at all. Maybe something like Nike Free or some sorta retro basketball sneakers? But even there I think you're heading into "extreme fashionista" territory and it's better to stick to Chuck Taylors or Golas or the like. Those Merrells which are styled like sneakers but in more conservative shoe-like materials would also be perfectly fine.
posted by Sara C. at 11:39 AM on December 4, 2013 [2 favorites]

Oh, and for the blazer itself I would go to Gap or Banana Republic or wherever he usually shops and pick something that they sell. That way you're sure not to accidentally buy part of a suit. Sales help should be able to help him pick something out, too.
posted by Sara C. at 11:41 AM on December 4, 2013

Okay. A sportcoat/blazer/odd jacket - those are all the same thing, a jacket that is not part of a suit.

I am assuming in the advice below that your husband isn't going for some kind of Raf Simons or Yohji Yamamoto or otherwise really avant-garde look - that he just wants to look like an average fashion-conscious fellow. If he were really ready for the Yohji Yamamoto thing, he probably wouldn't be posting this ask.

So, given that:

1. You don't want a jacket that looks like the suit pants went missing - so it won't be in a classic "suit" fabric or pattern like pinstripes or gabardine. You probably want a soft jacket without a lot of padding and structure, neither tight nor loose. You want a fabric that is attractive and distinctive in itself - a tweed, a herringbone, a nubbly wool, a heavy and distinguished wool flannel, an interesting corduroy, etc. For summer, you might think coarse linen, raw silk, interesting cotton. Think of this as analogous to getting a cardigan - you would not get a cardigan which exactly matched your pants, right? You would want the cardigan to harmonize but also to stand on its own, so to speak.

2. You probably do not want a double-breasted jacket - they are difficult to pull off.

3. You don't want a black jacket (unless you really do - ie, if you're going for some kind of new wave or avant-garde thing). Otherwise, black jackets are for funerals, certain types of nightclubs, actual black tie and working as a waiter or in an orchestra. They very easily look either generic or affected or childish - like you're thinking "black is a really cool color, it's all gothy!" or "black goes with everything!"

4. The third inspirational image is a cute photo, but not that great as a template - note how the jacket really is in a "suit" fabric and it's pretty stiff-looking. It looks fine on that kid, but that's because of who he is and the pose.

5. The canonical "jeans and jacket" situation would be dressy dark jeans, a corduroy/tweed/nubbly jacket, a nice slim-fitting tee and leather shoes or boots in a robust/country style.

6. A sort of trashier citified version would be dressy dark jeans, a black jacket in a fashion cut (shawl lapels, perhaps), and black glossy shoes or boots. Fit of the jacket will be super-important here. (Note that I don't recommend black jackets.)

7. Consider - do you want a "real" jacket or a fashion jacket? A "real" jacket in a nice fabric with a serious cut that won't look dated next year will be more versatile, more expensive and a little less trendy. A fashion jacket will be cheaper, fit less well and look dated quickly, but if you're hoping to look like a trendy young thing that's what you want - try H&M maybe?

8. Don't wear sneakers unless you really know what you're doing. It's not impossible, but I would start with a simpler outfit.

9. If this were me, I'd probably go with dark tailored jeans, a jacket in a black and white nubbly fabric that reads as grey or a grey tweed or a herringbone with greys and then either a very simple plain tee or possibly an ultra-ultra fine stripe in a very subfusc color and then some really simple black leather boots or shoes with a slightly chunky sole (not chunky a la Doc Martens, just not super sleek dress shoe. . If I didn't want leather boots, I'd go with simple canvas shoes without visible logos or wackiness from Vans/Converse/Keds/Common Projects/etc (Common Projects if you want to break the bank). I suggest this because it sounds like your partner wants something less "countryside" than the typical, which would be built around browns and olives and brown or camel boots.
posted by Frowner at 11:41 AM on December 4, 2013 [2 favorites]

His current pair of shoes would look hideous with a blazer. Comfy, slightly dressier shoes would be the way to go, and won't run you too much.

Honestly, I don't think I could answer this question well without knowing how your husband is built. The t-shirt and blazer images you've posted all worked because they were all being worn by models, and anything would look good on them.
posted by FAMOUS MONSTER at 11:42 AM on December 4, 2013 [6 favorites]

I hate to say it . . . but any look he goes for is going to be immediately invalidated if he's in those shoes. They are that bad.

I'd get him the jacket for Christmas, but on the caveat that he tries some different shoes on .
posted by Think_Long at 11:42 AM on December 4, 2013 [18 favorites]

Unfortunately, I'm not sure how much I can do about his shoes. I think his current pair looks like this.

Oof. There is kinda not much point in buying a blazer or sport coat at all if he's dead-set on wearing shoes like that. It will actually look much, much worse than just wearing the shoes with regular clothes. I mean, we all make our own fashion choices, but if he's actually interested in looking more put-together (and I'm not totally clear here if he is or if you're trying to push him in that direction), the shoes need to come first, or it's going to look worse rather than better.

Will he really not consider wearing anything more low profile, like maybe a pair of neutral-colour pumas or converse? Or casual leather shoes? You can easily find non-sneakers that are comfortable, non-flashy and non-trendy.
posted by randomnity at 11:43 AM on December 4, 2013 [2 favorites]

New Balance are a nice compromise between athletic and fashionable sneakers.
posted by Rock Steady at 11:43 AM on December 4, 2013

This is about the look he's going for, in terms of a specific product to buy and how to style it. I think the shirt they have it paired with is only so-so but isn't the worst. I would not do a plain solid colored one, though. Too 90s.
posted by Sara C. at 11:44 AM on December 4, 2013 [1 favorite]

not grey, black, charcoal - you don't want a blazer to look like its part of a suit he's wearing w/o the pants.

Make him buy a real pair of boots. Alden Indy's or something.

Personally I think the t-shirt thing is hard to pull off.

Also I think he could pull of New Balances or Converses with an Odd Jacket, but not an Odd Jacket, Jeans, and Athletic Shoes. But some form of Cotton Pant or Cords it could work.
posted by JPD at 11:46 AM on December 4, 2013

It's never going to work with those shoes. If he is not engaging in some kind of sport or physical activity at that exact moment, those shoes should not touch his feet.

This is basically my husband's "uniform":

Grey blazer

Navy Chinos; sometimes jeans

Untucked button down; occasionally, a plain t-shirt, but that's usually just to walk the dog or something

(In winter) V-neck wool sweater

Brown Clarks Desert Boots or Casual Sneakers

The key is to have at least 5 of everything (other than the blazer/shoes) in a variety of navy, grey, and black, so that there is zero to think about when getting dressed. Just grab one of each component and you're set.
posted by melissasaurus at 11:46 AM on December 4, 2013 [3 favorites]

I think you guys are too hard on those shoes. Yeah with Jeans no. But with Khakis and a subtler tweed it wouldn't look terrible. Ok it'd look terrible - but not clownlike.
posted by JPD at 11:47 AM on December 4, 2013

No, those shoes are gonna kill anything, sorry. Desert boots are the magical secret to looking put-together without wearing "real" shoes.
posted by neroli at 11:48 AM on December 4, 2013 [9 favorites]

I will suggest something a bit more casual to start off, he should feel comfortable because feeling it is half of looking comfortable and hence, good. Since it is winter, you can try a corduroy blazer which is good with a sweater if he wants to wear that. The one I linked is an olive color which is forgiving with any skin tone and goes with any color inside shirt. If he likes athletic shoes, how about something like this?

I think wearing a t-shirt (with or without a sweater) is fine under any blazer, but the t-shirt should be heavier weight and isn't something like a hands because the way the shirt sits will make you like or dislike the look. A collared shirt is nice but I think for the most part, it is what he is most comfortable wearing.

Get some crazy socks too while you're at it!
posted by Yellow at 11:49 AM on December 4, 2013

Why not get him either a structured cardigan or a knit/sweatshirt fabric jacket? Here is one from Land's End - I got one like this and it was pretty nice. They also have them in blue
or you can find knit ones like this which is dressier. Or why not this kind of thing? Or what about just getting a nice shawl collar cardigan, like this? These are all much easier to wear with a tee shirt, fit is more forgiving, they're more casual and so easier to mix with jeans and sneakers and they all look a little more dressed up than just a hoodie or sweatshirt. If you look around, there's lots of stuff like that this season - I'd be glad to suggest some more.

Except for the wool one, these could be worn with more sub fusc sneakers, even New Balances if you got the really plain kind.
posted by Frowner at 11:49 AM on December 4, 2013

I am willing to pretend that we live in a world where I can convince him to get new shoes so let's work with that.

He has several button down shirts, mostly striped. As far as his build, he's a small person - 31x30 pants, usually a size small in shirts. Most of his jeans are boot-cut but he's been wearing more slim cut. Not skinny jeans, though.
posted by kat518 at 11:49 AM on December 4, 2013

I would also add that unless he's a very normal size, I wouldn't buy it for him sight unseen. Blazer/sport coat fit is a little finickier (for me at least) than other fits. There's a bunch of places for it to go wrong. A lot of that can be solved by tailoring, but it's silly to spend $100 tailoring a $150 jacket would you can get it close enough the first time.

The other thing about those shoes (not to pile on) is that if his problem is standing out, those shoes stand out. They're bright and colorful and big. He probably feels more comfortable in them because he's used to them, but they in no way stand out less than a pair of black converse or casual brown shoes of the non-sneaker variety. Desert boots are trendy, but he might not know that, and they blend in well if they're not too brightly colored.
posted by Bulgaroktonos at 11:51 AM on December 4, 2013

When I clicked on the picture of those Brooks Beast running shoes that your husband wears I almost spat out my food from laughing so hard. NO... no, absolutely not, they cannot be worn with a blazer and t-shirt.

Here's the thing ... If he wants to pull off this look he's got to go all the way. Below the waist has to be as stylish as above the waist ... Otherwise it's sort of al sartorial mullet he's creating and honestly he should just stick with what he's been wearing and forget the blazer.

He needs to get nice shoes, nice premium denim jeans, a more stylish casual blazer made of a soft, stylish fabric, and perhaps a dressier/trendy t-shirt in order for this to work. And the difficulty is that, for this to work, may take more commitment than he's willing to give it ... especially since you mention he didn't like Converse because they seemed too trendy.
posted by jayder at 11:51 AM on December 4, 2013 [7 favorites]

BTW, in case it's not clear, I really appreciate the suggestions! I can barely handle what I wear so I really need help trying to figure out how to make him look awesome. Many thanks!
posted by kat518 at 11:52 AM on December 4, 2013

IMO nice dress shoes or dress boots or even desert boots are much more comfortable than sneakers, so if that's the issue maybe take him to a fancy shoe store and let him try some stuff on. If he's into zappos and online buying then one key to remember is that you will want to size down from his sneaker size.
posted by MisantropicPainforest at 11:52 AM on December 4, 2013

Ok it'd look terrible - but not clownlike.

If it's actually a thought that he'd be wearing this outfit with athletic New Balances, if they're anything but spotless, it will look like someone else dressed most of him (i.e. way too affected) and forgot the shoes.
posted by griphus at 11:52 AM on December 4, 2013

It sounds like I'm looking at getting him a sport coat and a pair of shoes. Then can he just add a pair of dark jeans and a button down shirt?
posted by kat518 at 11:57 AM on December 4, 2013

Also: Most of his jeans are boot-cut but he's been wearing more slim cut.

Do you have an H&M nearby? As skinny jeans gained prominence, they went from having "boot cut," "regular" and "slim/skinny" to something like five or six different varieties ranging from "slim cut specifically for guys that hate wearing skinny jeans but want to look like they are" to "these are just jeggings we can't call jeggings because dudes won't buy them."
posted by griphus at 11:57 AM on December 4, 2013

Some shoe options that might work and entice him away from the terrible sneakers:

Steve Madden
posted by brilliantine at 12:00 PM on December 4, 2013 [1 favorite]

It sounds to me from your additional comments like he can probably put together an outfit from what he has - are the jeans pretty dark? I think that's important. Super washed out faded denim screams "dad jeans" to me (probably because my dad was wearing a pair of 30 year old Levis at Thanksgiving). But yes, sport coat + relatively slim cut oxford shirt (blousy wont really work for the look he wants) or the perfect t-shirt + dark slim/not enormously baggy jeans + shoes (see below) = perfectly respectable outfit.

The only tricky spot here is the shoes. I agree with the consensus above: athletic sneakers will make him look unkempt and excessively youthful no matter what he's got on from the ankles up. If lack of comfy kicks is the concern, there are lots of comfortable 'sneakers' that don't look like you forgot to bring your good shoes to put on after the gym.
posted by hungrybruno at 12:01 PM on December 4, 2013

Take him to the Gap.

On this shopping trip, have him wear the jeans he'd most likely pair with a blazer, a button down shirt sans tie, and his new more low-profile casual shoes/sneakers/boots/whatever.

Find the sales person who works the men's section, or at least find a sales person. Ask to see some blazers. (Which is what they seem to be calling all the jackets like this, per their website.) From the Gap website, it looks like they don't have anything way inappropriate like suit jacket or anything black or double breasted.

Let the sales person help you pick the best option from the ones they have.

The best way to go wrong with this is to go to a thrift store or somewhere huge with a really wide selection (like H&M or a department store) and try on a million things which are all totally inappropriate. The nice thing about shopping someplace like the Gap is that they've sort of done the work for you in terms of not wearing something meant for a funeral suit.
posted by Sara C. at 12:02 PM on December 4, 2013 [1 favorite]

It sounds like I'm looking at getting him a sport coat and a pair of shoes. Then can he just add a pair of dark jeans and a button down shirt?

This thread is getting noisy (poor new balance sneakers), but yes, I think that is the takeaway. Gap should have good options for both.

Also, I'm about your husband's size, and I won't wear skinnies or most slims, but I really like the levi's 514 jeans - they are slimmish, but definitely not skinny
posted by Think_Long at 12:06 PM on December 4, 2013

The key to making this stuff work well comes from the small details that you might not notice at first, so I'll share a few. You will think that I'm over thinking this, but if you want it to look good then sweat the small details.

* Complexion and hair color. Does he have high contrast? Meaning, does he have dark hair and normal complexion? Another cue is that the eyebrows are quite visible. If so, work off of the high contrast with dark/light color. Choose darker jeans, light shirt and likely a neutral navy blazer.
* The T-shirt underneath just plain doesn't work unless the person is attractive (like a model) and they look good in pajamas. Most people just look poorly dressed in this combo. A button down shirt is a much better choice.
* Is he tall? Cuff the pant leg. This may or may not work, but it is worth trying.
* Is he short? Make sure the socks are similar color to the jeans. They should extend the leg visually.
* I think you said above he is thin. Pay special attention to the width of the shoulders on the jacket. The corner seams should align with where the shoulder ends. If they stick out (or God forbid hang over) it is visibly ill-fitted and it makes a person look like a pin-head. This advice actually works for anyone, but especially for thin people in jackets. The jacket should drape in a way that conforms to the body proportions. If it feels like a sheet draped over the shoulder it is wrong.
* Slightly shorter sleeves help make this look work. Just a little shorter than the length of the shirt sleeve is a smart look and if he has high contrast complexion it adds to the good effect.
* Shoes matter. They don't need to be dress shoes, but sneakers are strictly out. No, no no. I would tend toward brown instead of black.
* A lot of blazers have brass colored buttons. I would seek out ones that have more neutral tones. When paired with a tie and dress shoes the brass is a tight look, but regular buttons are a better complement to the casual jacket-with-jeans approach.
posted by dgran at 12:17 PM on December 4, 2013 [1 favorite]

The pair of sneakers you linked are an "absolutely not" for me, sorry. I'm not kidding when I say that a pair of Crocs would be more stylish. A pair of black Vibram Five Fingers might even look more fashionable, and I think those would still look silly with a blazer.

One of the reasons those sneakers don't work is that they are graphically very busy: lots of changes in texture, lots of overlaid shapes that aren't particularly "clean" looking, different colors together, matte vs. shiny, a complicated overall silhouette, etc. So they stick out a lot. And then, after the shoes have attracted so much attention, they look kind of like you went to go work out and then never changed, which is sort of a distasteful association for most people.

Despair not because the blazer-t-shirt-jeans-sneakers combo is definitely doable with different sneakers. I think the Pumas sound awesome, but I can also see why bright red Pumas might be a lot of look for someone who doesn't own a bunch of pairs of fashionable sneakers and would have to wear them pretty often. If he's just dipping a toe (ha) into buying sneakers and doesn't want to look like a super trendy Hypebeast, I would go for something with clean lines in black, white, grey, navy, or khaki/brown.

Here are some more specific suggestions. In addition to Chucks and Vans, PF Flyers would work. Saucony Jazz might be a nice bridge between his current style and something more fashiony as well. Rock Steady's suggestion of New Balances is good with the caveat that it should be one of the "classic" styles - NB makes a lot of shoes that look like the sneakers the OP linked as well. A more subdued pair of Pumas would be fine as well. Adidas Sambas also work (I think they even make some with a black sole instead of green, which isn't totally necessary but would look even cleaner). Clarks Desert Boots will look super dope with this type of outfit but are spendier and less sneakery, so they might not be 100% what he's after.

Skinny jeans aren't necessary, but he might want to consider "slim fit," which often make people look trim without either crushing their junk or making them look too early-00s Williamsburg. The blazer absolutely must fit properly in the shoulders (not protruding out from them or bunched up around them) - you don't want to size it like an oversize hoodie. My personal advice would be to look for colors that contrast with the jeans a little (e.g., a darker blazer with light, faded jeans or a light blazer with super dark indigo jeans) but this may be less essential and more my own opinion.
posted by en forme de poire at 12:19 PM on December 4, 2013 [1 favorite]

I think you guys are too hard on those shoes.

Not possible. They are that bad.

I'm saying this not out of malice but out of empathy, because I used to commonly wear frumptastic athletic shoes like this in normal situations, and it is one of my biggest wtf-cringes when I look back on photos from that period of time. About the only person I can think of who sometimes just barely gets away with this is Dr. House, and 1) he is supposed to be a sort of ultra-nerdy, antisocial "type," 2) he is played by Hugh Laurie, and 3) his athletic sneakers are significantly more stylish and well-taken-care of. (And you'll also notice on that page Dr. House rocks Chuck Taylors or skate-type sneakers in a bunch of episodes, and they look really good on him.)
posted by en forme de poire at 12:35 PM on December 4, 2013 [1 favorite]

This is my style! I wear a jacket (I have couple), solid button down shirts, and either decent khakis from j crew or dark jeans, and brown Frye's oxfords.

Agree that the sneakers have to go, but I'd also like to suggest that he get jeans that aren't 'boot cut' too. Instead of the Gap, I'd go to J. Crew (or Banana Republic)--it's a little more expensive, but my experience with the Gap has been that their clothes (at least recently) have been really low quality. J Crew's not that expensive but the quality is better, and a little more classic. That's not to say you can't find good stuff at the Gap, but if he's the co-founder of a tech company (and over the age of 30) it might be ultimately a better investment to spend a little more on a nice jacket, shoes, and jeans.
posted by drobot at 12:45 PM on December 4, 2013 [1 favorite]

The reason I suggested Gap is that the husband already shops there, and because they don't sell suits, it's basically impossible to go wrong with any sport coat type thing in the place.

At J. Crew I think you'll really need to rely heavily on help from the sales staff in the menswear section. And may even want to opt for their "personal shopper" service if it's available in your area.
posted by Sara C. at 12:57 PM on December 4, 2013

Seconding Adidas Sambas. When I think of the jeans + blazer look, I see only Sambas as the proper footwear of choice. I want to get a pair myself so I can rock this look (I'm a girl, but my style icons are mostly men, for what it's worth).
posted by dearwassily at 1:07 PM on December 4, 2013 [1 favorite]

nthing "Can't do anything to improve his look if those current shoes are involved" so you have to focus your energy on getting better there, if you/he are interested in making style improvements.
posted by Kwine at 1:18 PM on December 4, 2013

A waist coat over the tshirt with a matching jacket is a nice look and might cut back on the miami vice try too hard vibe, that or an open button down shirt, something to add an extra layer to the look. He is going to have to suck it up and get a nice pair of shoes.
posted by wwax at 1:48 PM on December 4, 2013

I dress somewhat like that for work. I do think some of the options you're looking at are basically options for people with a pretty refined sense of style and excellent awareness, and with no judgment whatsoever, your husband does not sound like one of those people.

Lose the t-shirt/polo idea, it's too hard to get it right. Dark jeans are definitely a must for this look, imho, and the jacket needs to fit well - I don't know your husband but my experience with guys that don't really get into fashion much is that, especially for the upper body, they have a tendency to go too large. A blazer or jacket that's too large renders an outfit shapeless, and makes the man wearing it - especially if they have a small frame - look like a high-schooler wearing dad's suit.

So I would definitely wear it with (well fitting shirts), tucked in or not. Johnny Lee Miller in Elementary rocks this kind of looking quite well, imho, and he's slim.

I can no longer find it on the US site, but when my wife was in the US recently, I got her to pick me up this little number from Uniqlo. I like Uniqlo, cause they're cheap, and their Japanese cuts suit my thinnish frame.
posted by smoke at 1:51 PM on December 4, 2013 [1 favorite]

okay triple post extravaganza! I just wanted to say something about the mental/philosophical part of this really quickly. As another nerdy dude I had a lot of weird and often self-contradictory mental baggage about clothes growing up, and I think this isn't uncommon. I don't know if any of my problems are relevant to your husband, but I'll list them just in case. One problem was that I really did want to feel confident and sexy, but I also felt like I somehow didn't deserve to: it was almost like dressing more smartly was "above my station" as a skinny, gangly, somewhat socially awkward nerd, like it would be putting on airs. It's like this comic was drawn just for me! I also had internalized an idea that caring about appearances was something that only shallow, materialistic people did and that I should be "better" than that. Finally I thought that by dressing for style instead of comfort I was revealing something about myself that other people would judge. (This was both metaphorical and literal: one of the things I was self-conscious about was the shape of my body, so I dressed in a lot of tent-like clothing, etc. But it was also revealing things like "I like this type of fashion" or even "I like these colors.")

Eventually I realized that in my case, this was mainly anxiety twisting my thoughts around and inventing rationalizations for itself. If you want to prioritize the life of the mind, or if you want to judge people on their behaviors and not their appearance, you can still do that without having to be some kind of freaking clothing martyr. Even very moral people don't all wear sackcloth and ashes everywhere, and of course most people express their values in much more important ways than by the kind of sweater they put on that day. And of course, the idea that if you're a nerd with an outlier body shape it's "inauthentic" of you to want to look snappy and sexy and yes, even fashionable in the clothes you wear, is just nonsense. (Ironically, there I'm judging myself based on my appearance, even though that was ostensibly one of the things I was railing against.) Plenty of people find a harmonious, moderate path where they select their clothing based on what they personally like, but also keep the role of clothing in their lives in perspective.

You may have noticed that a lot of these ideas I had conflicted with each other and don't even make a lot of logical sense. In my case they turned out mostly to be elaborate mental wallpapering over the fact that I was very insecure about my appearance and feared other people's judgments, so I was trying to anticipate them and immunize myself against them pre-emptively. By doing this I was basically giving random people veto power over my appearance - and not even real people, let alone people who shared my values! I was also magnifying the importance of not making mistakes, convincing myself that I couldn't bear it when actually it really wasn't that big a deal if someone thought I had made a fashion faux pas. Once I started to realize this, it became much easier to exercise more intentionality in what I was wearing, and to allow myself a little freedom to play and even to make mistakes in how I presented myself.

Again, no idea if this even applies a little to your husband, and really sorry for the book of text that doesn't exactly and directly answer the question - but tl;dr, I just wanted to say that f'ed-up ideas about body image can be some majorly toxic shit even for reasonably-affluent male nerds with some advantages in life, and that if you discover that's been influencing how you dress, it can be very liberating to uproot those brainweeds and throw 'em in the trash and have some fun and wear the shit out of some bright red Pumas.

(Or for that matter some hiddy athletic sneakers if on balance, you'd rather wear them, all things considered. lol, j/k. but seriously, if they make you happy and you like how you look in them then you should still wear them because ultimately, this is an area where your opinion is more relevant than mine.)

And yeah not sure how I forgot Onitsuka Tigers, that's a great choice IMO if you want something understated but nice-looking.
posted by en forme de poire at 1:51 PM on December 4, 2013 [16 favorites]

(also if you have bright red sneakers and want to take the edge off them, I would try pairing them with slim-fitting medium-brown pants, whether they're khakis or denim. blue jeans will make the red stick out more; brown tones should make it blend more. now I want to buy some red Pumas.)
posted by en forme de poire at 3:04 PM on December 4, 2013 [1 favorite]

IMO trying to incorporate a blazer into his wardrobe would require too many changes, and if you're not really knowledgeable about fashion it's easy to make a lot of mistakes you'll come to regret in a few months. He would need new shoes, new jeans, would need to start wearing shirts...that's a lot of stuff to get when he's not even really sure what he wants. If he's new at this then he absolutely should not spend too much money, because his ideas about proper fit and color and texture are probably still nascent. The men in your example photos can pull it off because they're handsome, and even still many of them look a bit goofy to my eye, and would probably look better wearing button down shirts.

So there are two options here: (1) get a blazer anyway and just rock it. If you want to do this then just goto H&M or Zara and get something <$100 and accept that he'll probably look goofy but maybe he'll learn something in the process. I would suggest something in brown or navy blue with a texture like herringbone or corduroy. (2) build up to the blazer. Easiest upgrade would be shoes. You can find Clarks desert boots on sale and they're extremely comfortable. Like the blazer, they instantly make any outfit classier. A thick wool cardigan from J.Crew or Club Monaco is a nice alternative to a blazer, and is informal enough to be paired with t-shirts and sneakers, but can also be dressed up with sneakers and boots.
posted by rq at 3:50 PM on December 4, 2013

Wear the New Balance Classics in neutral dark grey or navy blue or Adidas Sambas.. there are lots of sneakers that are not running shoes and look good and are not flashy or try hard - this is the kind of thing I go for, because I have huge feet, so I don't want to draw attention to them either. Wear classic jeans that fit properly (not sloppy baggy or dad jeans style and no funky washes).. Does he look good wearing a plain t-shirt that isn't all baggy?

Those blazers you picked out seem fine; I would start at J Crew, their men's stuff is not flashy and they seem to do little/no wrong with it - I wish they made it in women's cuts and I'd wear it myself. I notice they are being worn with chinos - that really seems like the better way to go over jeans. And honestly if he doesn't feel comfortable in a blazer, and doesn't have to wear one, why wear it? If he just wants to look nicer, why not buy nicer versions of the kinds of things he wears now. If he wears hoodies, get a nice quality, classic, stylish hoodie, if he wears sweaters, get a nice merino or cashmere that fits well. Above all he should feel confident in his clothes, not awkward.
posted by citron at 3:55 PM on December 4, 2013

Here's the other thing about buying a blazer: learning how a blazer fits is _hard_. It's one of the hardest things to learn about mens wear. There are all sorts of small details he has to learn so it's almost guaranteed the first blazer he buys won't fit perfectly. Everything from shoulder width, lapel style, lapel width, sleeve width, sleeve length, armhole size, jacket length, button placement, button count, vents, material, color, texture, etc. Even if you go to a reputable store like J.Crew it's very easy for him to buy the wrong size or a bad lapel style, and there's no guarantee that the SA has any idea what they're doing.
posted by rq at 4:07 PM on December 4, 2013

There are some great deals in snappy blazers at thrift shops, but this means going thru some really jazzy-looking stuff that exactly doesn't fit before you find what does. Consider dark T-shirts or dark turtleneck-ish items. For chouse, Blundstone boots or nice desert boots.
posted by ovvl at 4:41 PM on December 4, 2013

Wear the New Balance Classics in neutral dark grey or navy blue or Adidas Sambas

Oh, no. I can see that on a hip type with a fashion-conscious look, but apparently the order of the day is to de-dorkify. A guy with the shoes linked is not going to comfortably step up his game to those tennies with a blazer; I think there will be pleated Dockers inbetween, and that will wreck it. I would suggest lower-risk options. (Converse All-Stars are the best compromise shoe, I think.)

But I agree that this might be reaching; I cannot see making a leap from those sneakers to Pinterested model looks. Guide him to more traditional looks; think preppy. Corduroy? Was the 'blazer' idea just a general 'step up appearances' idea? It is hard to bollocks up a cashmere sweater; it can go over a tee or a dress shirt, and under a jean jacket or a sharp wool blazer, and it will class up old khakis.
posted by kmennie at 5:10 PM on December 4, 2013

I can't imagine my man in corduroy or tweed. We've been together 10+ years and I've never seen it happen. I agree that his confidence in his clothes is really important but I think there's a middle ground between being on the edges of your comfort zone but feeling good. Like when I go out in a low cut dress or rock a suit - these looks are not what I would normally wear but sometimes they are absolutely right for the situation.

My dude is in a weird place because he can get away with being in jeans and hoodies - he's a tech guy at a startup and he's young. But he knows he can't wear that when he meets with investors and that's a situation where he needs to be confident and look good. He can't look like he borrowed his dad's clothes.

I'm hopeful that if we can figure this out, maybe he can look a little snazzy maybe once a week so it won't be unusual for his colleagues to see him like that and he'll feel more comfortable dressing like an adult so when he has to, it's not an ordeal. Is that reasonable?
posted by kat518 at 8:50 PM on December 4, 2013 [2 favorites]

Late to the party but the only Converse I'd suggest would be (off-white if you can find them) Jack Purcells. Khakis. Crew neck or v-neck cashmere pullover with white t-shirt underneath. Per this fellow.
posted by TWinbrook8 at 10:45 PM on December 4, 2013

It sounds rather as though you might want to read Put This On - here is a very short post on "IT dressing" and here is their take on the "essential man's wardrobe". Put This On is a pretty solid style blog in that it does not assume that you're going to start wearing bespoke Italian fashion or flying to England for your country shoes; it's not racist, unlike some of the others; and it has a mixture of suggestions for clothes ranging from tee-shirts on up, instead of just focusing on suits. If you like fashion at all, you might get a kick out of clicking around in the archives - if you go back to the beginning, you'll find a lot more general-purpose posts, and it may give you some ideas for general "dressing a bit nicer sometimes" clothes.
posted by Frowner at 6:53 AM on December 5, 2013 [2 favorites]

I add that the "essential wardrobe" linked above is probably a little conservative for an IT dude. If your fellow were to look at some men's style blogs (PTO links a bunch) to get a feel for just what "slightly dressier" looks like, he could probably ring some changes on the list - ie, for basic shirts, don't get light blue and white but instead get a stripe and a dotted (or other small repeating pattern) shirt; don't get khaki-colored chinos, get olive or grey or navy; don't get black captoes, get blue suede loafers; etc.

The key with the "essential wardrobe" business is to make sure that things won't date too fast* and to make sure that almost all of them work together.

So I really like blue. The majority of my wardrobe is blue - blue stripes, blue solids, blue patterns, all in varying shades from very light to dark navy. The things that are not blue almost all work with blue - so I have grey pants and camel pants and beige pants and rich chocolate brown pants and olive pants, and I have grey sweaters and green sweaters and camel sweaters, etc. I don't have a lot of purple or pink or red or yellow because those are much harder to pair with blue, even though it's not impossible.

When I put together an outfit, I avoid head-to-toe blue, unless I'm really varying the color. So in the summer I might wear navy pants and a light blue shirt. I'd probably wear a camel belt and camel loafers for accent. I might conceivably wear navy pants and a shirt with a navy-and-white pattern, but only with some patterns. The goal is to establish a harmony among similar elements.

There are times and places where matching is fashionable - fifties women's clothes, sports-influenced fashion (where you'd wear some kind of deluxe track suit, for instance). Right now, today, too much matching is not fashionable for dressy men's clothes. So no navy suit/navy shirt/navy tie (unless you are a tenth level style ninja and have a plan).

*Patterns get dated at varying speeds. A very plain stripe won't date much; a wide stripe or a stripe in an unusual color combination will. Dots, florals and little patterns will look dated within five years - if they aren't part of "your look". So if your look is "floral shirts of all kinds", you can wear any kind of reasonably attractive floral shirt and it will just be your thing, but if you have only one, it will look dated eventually because the fashionable color palette will have changed a lot, or the fashion will be for large florals and yours are tiny, or for stylized flowers and yours are realistic, etc.
posted by Frowner at 11:14 AM on December 5, 2013

Nthing Clarks Desert Boots - Amazing how versatile these can be with this look. Also, I found this look hard to pull off without a great sport coat. I've had a lot of success with Hackett - Worth every penny if you take care of it!
posted by LongDrive at 6:48 PM on December 6, 2013

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