I don't know how to dress myself.
September 24, 2015 5:22 PM   Subscribe

I need to start dressing more professionally, but I'm terrible at it and the sort of person who would happily wear t-shirts and shorts or jogging pants all the time if it were acceptable. How can I get better at this?

I (a male in my mid-30s, business casual office) want to start dressing more professionally for work. I'm not in a senior role, but my job involves talking to a lot of people who are at the management level up to the executive suite in my organization.

I have a few issues, though:

1) I am really bad at taking care of clothes. The laundry gets done but I'm not good at keeping up with things like ironing, for instance. It takes me forever to do one shirt and it feels like a colossal time suck.

2) I have a very limited sense of what I like. I have dress shirts and khakis and dress pants but nearly all of my dress shirts are some variation on the colour blue, sometimes with some kind of pattern (checks or stripes or whatever). I think I have one that's grey, and that's about it. I just don't think any other colours look very good on me. I have a vague sense of a "look" I like in terms of fashion (like, a cool professor maybe?) but it seems to better suit thinner people than me.

3) I have a weird shaped body. I'm a fair bit overweight, but if I get a shirt that has the right neck size, the rest of it is like a tent on me. If I get one with a smaller neck size and don't plan to wear a tie, it's too tight around my belly or too tight around my shoulders. I also have large, muscular legs, and finding pants that fit is an ordeal as well. Again, if I get them to fit in one place, they are huge in another place.

4) Because of #3 (and because I am heavy in general) I don't like clothes shopping. It's frustrating and annoying and it's impossible to find stuff. As a result, I don't want to do it and so wear clothes for a long time and they fade and start to look worn and I hold on to stuff well past their natural life spans.

5) I find it really hard to justify to myself spending money on clothes. I can't get out of the mindset that it's frivolous. Couple that with #4, and, yeah. I also always want to lose weight, and so I find to tough to justify spending money on nice clothes when in my head I am going to lose weight and make them all too big.

6) Because of my weight/body shape, I find it hard to believe that anything will look good on me, so I think I just don't bother trying. When I was thin I liked clothes shopping much better because stuff fit and looked good.

So how can I do better at this? How do I build a wardrobe?
posted by synecdoche to Clothing, Beauty, & Fashion (17 answers total) 10 users marked this as a favorite
Get yourself to a tailor!!! I can pretty much guarantee that any person you see who is well dressed and looks sharp but is not model-sized has gotten their clothing tailored to fit their body. It's such an important investment (and not THAT much money), and it will likely make you feel so much better about your body and how you are dressed.
posted by dysh at 5:34 PM on September 24, 2015 [2 favorites]

I don't directly have experience trying to fit mens clothing, but I've helped my husband in the process of getting some nicer-looking clothing that fits well with a body type that doesn't match widely available clothing proportions. I think a big part of what you need is a tailor. Yes, it's going to be more expensive, and I know that justifying expense is also part of your concern here, but it will help so much with getting clothing that fits, and that will, in turn, help you feel better in your clothes. I would stay away from places advertising "alterations" and try to find an actual tailor -- they have more experience with more complex changes to garments.

It sounds like khakis and blue dress shirts are what you're most comfortable with right now. What I would recommend is to take one of each (maybe a couple shirts) to a tailor and have them fitted. When buying clothes to be tailored, you want them to be big enough everywhere -- you can take away cloth, but you can't add it back on. If you have some pants and shirts that fit on the loose side of well, you can probably take those in instead of having to buy something new, but make sure they're of good enough quality that they'll last a while. A good tailor will be able to tell you if the items are a good candidate for tailoring, and can probably help guide you in how to choose sizes for your particular fit issues.

On the laundry front, you'll probably be better motivated to take good care of your clothes once they feel and look better, but it's also important to be realistic about your own habits. If you know you're not going to do much ironing, buy easy-care pants and send your shirts off to the dry-cleaners. I can't imagine actually consistently ironing mens dress shirts on a regular basis, much less appropriately starching the collars and so forth.

Once you've had a few things tailored and decided it helps, then you can start exploring your style a little more if you want. If you have some friends on the more stylish side, see if they can suggest some things they think would suit you well. But, as a man, you can also probably get away with pretty much the range of outfits you describe if that's what you're comfortable in.
posted by duien at 5:40 PM on September 24, 2015 [4 favorites]

Start at the bottom. What kind of shoes are you wearing? Wearing nice shoes will help pull the rest together.
posted by kellyblah at 5:52 PM on September 24, 2015

One thing that a lot of people don't realize is that the vast majority of off the rack clothing fits nobody "properly". Your body is NOT shaped weird. Your body is probably pretty darn normal. Most men's work basics come from a tradition of everything being tailored, because it used to be the case that suits were made to order, from scratch. This wasn't very long ago (fifty years?) and standard patterns and sizes haven't shifted much, and you may already have experience with suits being tailored to fit.

Basically, get yourself a tailor. If you are uncomfortable finding one, go to your nearest Nordstrom and talk to any salesperson about tailoring and they will leap on you with enthusiasm, but you can use things like Yelp or asking in a nicer small men's clothing boutique in your area for their suggested tailors nearby. It really isn't that expensive and is absolutely worth it.

What you do when you know you will be getting clothes tailored after purchase is to get things of high quality material and construction that fit you at your largest measurement and are big everywhere else. So for you it sounds like that would be your neck? This will vary by garment. It is also probably a good idea to stay away from trendy things, since these would be long-haul clothes and you sound like a guy who prefers the classics anyway. Then the tailor will be able to take everything else in. If you are planning to lose weight, that is okay! You can get your clothes tailored again if your body slims down and stays that way. Remember, you can always make clothes smaller, but you can't ever make them

As for laundry, one big help is actually how you store your clothes. I find it a thousand times easier to put stuff on hangers than to fold them, especially shirts, which are impossible. Think about getting thicker hangers (wooden ones are often wicked cheap on sale at places like bed bath & beyond) which will help your shirts hang better at the shoulders and space them apart so they don't squish against each other and crease in the closet. Pants are the same - depending on their material, if you give them a good smooth and hang them carefully with the leg crease as it should be, you should only need to iron for special occasions. If your closet space is lacking, you can get a free-standing clothes rack.

When it comes to colors guys have it pretty easy unless they want to deliberately mix it up. There is nothing really wrong with having mostly blue shirts. Blue goes with everything (think about all the things people wear with blue jeans) and is flattering with all skin tones. Other colors that look good on really, honestly, everyone: a rich red, soft cool green, charcoal black, coffee brown. If your skin is darker, try lighter colors like buttery yellow and silvery grey, and if your skin is lighter, try darker colors like plum purple and navy.

If you are nervous about mixing colors and patterns and neutrals, a good guideline is to have one color, one pattern (which can be a second color also or instead) and the rest
neutrals (neutrals are black, white, cream, brown, silver, grey, and darker/less intensely blue navy). So for example, a green shirt, a polka dotted tie, and black slacks with black shoes and belt. Or, a checkered shirt, a solid red tie, and brown trousers with brown or black shoes and belt. Or, a blue shirt and pinstripe pants with navy shoes and black belt. Or, brown tweed suit jacket with those professorial elbow patches with with matching tweed slacks, blue shirt and brown striped tie. You can get more complex than the 1c+1p+Xn guide, but it is a good place to start. You can also go for ALL neutrals, which can read as very serious and businesslike.

Think about the money as an investment in yourself and in helping people perceive you as you want to be perceived.
posted by Mizu at 6:05 PM on September 24, 2015 [3 favorites]

First of all, I'm with kellyblah, start shoes first. I suggest light brown leather (and a matching belt, I'd recommend Mission belt as it's super awesome).

After that, decent slacks shouldn't be to much of a problem, just get them tailored.

I'm with you on the neck thing (and used to be on the weight issue as well, thanks /r/keto/, so I'd start with nice polos. Check out Banana Republic.

Even w/out losing weight, you should be able to choose some nice outfits for work. And once you do, getting rid of clothes is going to feel liberating anyway. Side note, if you're really ready to lose weight, mefi mail me and I'll give you a rundown of what worked for me.
posted by pyro979 at 6:06 PM on September 24, 2015

I can't suggest anything specific clothing-wise but I do know the Male Fashion Advice subreddit is a very popular resource for some answers to your questions.
posted by girlmightlive at 6:18 PM on September 24, 2015

I hate ironing. When possible I buy non-iron dress shirts (the brooks brothers ones are my favorites), and for ones that do need to be ironed, I send them out to be ironed and pressed. They do a better job than I do, it's not that expensive, and life is too short to spend it ironing shirts.
posted by primethyme at 6:23 PM on September 24, 2015 [2 favorites]

We had great luck with these: Chinos with good fit and extended sizes . Also, dress to fit your body just as it is today, weight loss be damned. You will feel so confident in yourself.
posted by Sweet Dee Kat at 6:23 PM on September 24, 2015 [1 favorite]

If you hate shopping: find a store online that has free return shipping or something like $6.95 return shipping, then buy shirts and pants in a a few different sizes, and definitely one or two different pants cuts. You'll know what fits, you return what doesn't, and you buy more in the sizes that fit. Or, go somewhere that has a tailor on-site like Jos. A. Banks and they are more than happy to help you out. After 7pm on a weeknight is pretty quiet. If you're self-conscious about that, let me say I'm a woman who primarily wears mens' clothes and I had to go there to get a suit tailored for my sisters wedding and they treated me wonderfully; friends in other cities have had the same experience. And I don't iron, I just hang dry my clothes as soon as the wash cycle ends and smooth wrinkles immediately. (I air dry clothes not because they are dress clothes but just because I air dry clothes). If you use a dryer, just hang them ASAP after the cycle is over.

Colors: if you get classic checks/stripes/plaids in any color they look pretty damned good on anyone. I like blue, but I've added purples, greens, oranges, reds, and yellows to my repertoire and I love them and I look pretty damned good. And go all out with socks. I decided I was going to be fun from the ankles down and have roosters, robots, dinosaur, bicycle, argyle, stripes, and octopus socks in all kinds of colors and I get compliments on them all the time and it makes me feel pretty great.

Nthing shoes: get a few pairs of nice shoes - even just one good brown and one good black. Fancier shoes are so much more comfortable than cheaper dress shoes. I walked 6 miles in some Banana Republic wingtips one day and felt awesome afterward. You can get Cole Haan at DSW in the outlet section for ~$100 - also at Amazon or 6pm.com.

No pleated pants. You get what effectively looks like a crotch parachute and it draws attention there and there's just no reason.
posted by good lorneing at 6:25 PM on September 24, 2015 [1 favorite]

I hate ironing too. Then I got a clothes steamer. Changed my life. It's faster, easier, and takes up way less space. I hardly ever iron these days but my clothes still look good.

Also, nthing hanging instead of folding and finding a good tailor.

It's way easier said than done, but try not to dwell too much on what you think you should weigh. People of all sizes can look good, but a large part of it is being comfortable in your own skin. Confidence is the best accessory.
posted by AV at 6:42 PM on September 24, 2015 [2 favorites]

I also always want to lose weight, and so I find to tough to justify spending money on nice clothes when in my head I am going to lose weight and make them all too big.

I struggle with this from the reverse direction. I'd consider that in effect, you're kind of punishing yourself for not being the right size by not doing something you can do and want to do just because you're "too big." I think this is not only needlessly cruel to yourself (all other things being equal, don't bigger guys deserve nice clothes just as much as slimmer guys? Would you tell a friend of yours that they shouldn't buy nice clothes because they're too heavy?), but also potentially counterproductive: after all, there's research that suggests that shame and stigma hinders weight loss. And feeling more confident by dressing in a way that pleases you, given of course whatever other constraints you happen to have, can give you more energy to tackle other things in your life. You can also often get favorite items of clothing tailored after weight loss, and in the worst case, you can donate it and pass something nice on to someone else with your "old" shape, so it doesn't have to be "wasteful" in any cosmic sort of way.

Also, yeah, tailoring, oh my god. The extra nice thing about tailoring is that it can also transform thrift store purchases as long as certain key measurements fit: for example, if a second-hand dress shirt fits in the shoulders and is long enough in the arms, you can pretty easily have the rest of it taken in to flatter your body. Tailoring can easily cost more than the garment in this situation (e.g., if you paid $5 for the shirt) but it will still cost less than all but the cheapest off-the-rack dress shirts and will look way, way better.
posted by en forme de poire at 6:44 PM on September 24, 2015 [2 favorites]

If the second problem you've listed can be rephrased as 'I can't figure out what pieces of clothing to buy in order to assemble a style/wardrobe I like', that's a problem I had when trying to upgrade my work clothes too. One thing that I found helpful was Pinterest - I set up a board and just scrolled through the women's fashion tag, or business casual, or whatever for ten minutes every few days, pinning anything that jumped out as appealing (and trying not to over think it). Once I had a bunch of images I liked in one place, it was way easier to see trends and generalize to what things I should look for in stores.
posted by anne_severson at 7:20 PM on September 24, 2015

How do you want to look? How do you dress now? Do you want to be wearing suits? I'm assuming no, since your office is business casual. But even 'business casual' can mean a lot of different things, so I'll just describe the office wardrobe commonly worn in the Northeastern US/Canada. Fortunately, for men it is extremely simple:

No jacket, button-down dress shirt, no tie, collar unbuttoned, belt, slacks, dress shoes. Basically something like this.

I see tons and tons of guys wearing this exact uniform in NYC every day. I also wear this uniform. There's really not a ton of room for variation, except in quality and fit. And as regards quality, I honestly think past a certain price point it's indistinguishable.

2) I have a very limited sense of what I like. I have dress shirts and khakis and dress pants but nearly all of my dress shirts are some variation on the colour blue, sometimes with some kind of pattern (checks or stripes or whatever).

I think 90% of the male office working population of the US is like this. Some of my coworkers definitely wear a white button down shirt every day of the week (I'm presuming they change it of course) and they look plenty professional. White, blue. Maybe pink ("salmon"). Checks. Again, not a ton of variation here (nor need for it).

Generally: White or blue shirt. Dark grey or dark blue pants. Dark brown or black shoes. Belt same color as shoes.

3) I have a big neck relative to the rest of my body too. I generally buy shirts to fit my body and don't button the collar because I rarely need to wear a tie (again, business casual). When I do need to wear a tie, it's a tad uncomfortable, but as long as it's not choking you, it's fine.

There are online services where you measure yourself, pick a fabric, and they'll make the shirt to your measurements (for example ModernTailor). I've ordered a few shirts and it's been hit or miss (mostly, finding good fabric is the most difficult part) but some people really like it. Alternately, find a traveling tailor and have them make your shirts (you meet them for measurements then they have your clothes made abroad and sent to you). I don't think in-person bespoke tailors are worth the expense if you live in a Western country unless you have some serious dough to drop on clothes.

However if you are a "fair bit" overweight as you say, then either you will need to go for the "blousy" look which will give you some room, or the shirts will feel tight around your gut. I've seen both; it's personal preference; in both cases it's obvious the person is overweight.
posted by pravit at 7:33 PM on September 24, 2015

Oh and go get yourself some brand new underwear (I'd suggest boxer briefs) and socks. If you're anything like me your underwear and socks are old and worn, and new ones will make you feel great. Throw the old ones out.

Something else I thought of... now that is getting colder, there are really nice sweaters and vests that might be flattering as well.
posted by pyro979 at 8:01 PM on September 24, 2015

If going to a tailor sounds too intimidating, consider going to a store that has an in house tailor. In the Boston area, Nordstrom rack and K & G superstore are both reasonably priced options. If you have one, bring a friend who likes playing dress up and they might even enjoy getting to spend your money picking out outfits.
posted by fermezporte at 4:25 AM on September 25, 2015

My go to recommendation for this is Dappered.com. It won't necessarily help with you with the body shape and fit issues, but it will help with selecting business casual appropriate clothes. The forum is active as well and might be a good place to either research or seek advice.
posted by cnc at 11:20 AM on September 25, 2015

There is nothing wrong with wearing mostly blue shirts. Blue button-front shirts are extremely versatile, and it's not uncommon for very well-dressed/clothes-conscious men to own more shirts in blue than in white. (Added bonus: blue and other relatively-darker shades than white tend to be visually slimming, especially when patterned with stripes or grids/gingham. White anything is going to look "bigger" because it reflects more light.)

Basic Fit Maneuvers: Tailoring or custom-ordering clothes is often the only way to make sure most brands fit right, even for slimmer people. As you get your bearings, anyway. If the shirt fits comfortably in the neck (i.e. no looser than necessary to slide a finger in there), and the shoulder seams hit on the tops of your shoulders, adjustments can be made to sharpen up the fit around the middle of most shirts and jackets. Proper sleeve length can make a world of difference in the perceived fit of an item, too. Likewise, baggy-looking pants can look much sharper if the hems (and/or leg openings) are adjusted, not to mention that many are adjustable in the waist; this means that something that fits well on your thicker legs could be made to fit elsewhere, too.

In any case, do not buy the lie that a man's shirt needs to be skin-tight to look good. This is a very modern trend, and you want to avoid trends. Few people look good in super-tight clothes. A dress shirt/sport shirt should -- classically -- look reasonably trim, but still allow movement and comfort. Think of the way it hangs on the torso as being almost a tube; it's fine to have a bit of extra material at the waist, and preferable if you have any kind of love handles/belly. Don't be afraid of pleated pants, either; no-pleats-ever is also a trend, and they can make pants hang better on rounder people.

Less Basic Fit Advice: Once you and your tailor get a sense of your measurements, and what you look good in, it's easier to buy things online. This means you can better judge whether something will look right without tailoring, and feel safer about spending up for quality/longevity. I've found that many brands offer decent shirts and pants that fall in a nice middle ground, between so-called "classic" fits (blouse-y tent-town) and "slim" fits (sausage casings, on many bodies), and don't require additional adjustments. Try Land's End or L.L. Bean in their Tailored or Slightly Fitted lines, respectively. Or -- for a few more bones -- Brooks Brothers (I've had the same handful of BB shirts for so many years now, that I've lost track). Knowing your basic dimensions means you can easily buy used things on eBay, which allows much finer clothes, at a more "justifiable" price.

Color, Random, Etc.: Man, if you can get away with it at work, wear sporcoats. They are specially designed to exaggerate "manly" bits like chests and shoulders, while minimizing waists. My body is on the higher end of "average" in terms of muscle-to-fat, and coats are a godsend for me. Don't go crazy with colors and patterns until you've really gained a sense of what fits and etc. Focus on finding favorite/versatile color combos, instead, and "mix things up" via texture instead. And yeah, invest in some real shoes. There are many options now that are way better-made than your DSW-type brands, at roughly the same price.
posted by credible hulk at 3:22 PM on September 25, 2015

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