'Cause Every Girl's Crazy 'Bout a Sharp-Dressed Man
May 23, 2008 12:37 PM   Subscribe

I'm a very overweight man in my early to mid-thirties, and I would appreciate your advice as to how to dress in a way that's complementary to me for social situations (such as going to clubs, bars, lectures, etc.). More inside.

For a while, the environments I've dressed for have been my home and my workplace, with the occasional visit to a social situation. My work clothing has been short-sleeved polo shirts (of very nice quality) in solid, darker colors, and black Dockers. My home clothing is usually a T-shirt or sweatshirt, and a pair of jeans or shorts, depending on weather. If I went somewhere that required me to look nice, I'd wear the work clothes. Without intending to sound immodest, I don't think I look too bad in either "mode", but I'd like to expand a bit.

I'm intending to venture into some social situations I've not gone into before, and I'd like to look stylish. I may visit some bars and clubs here in Chicago; I may attend some semi-formal semi-casual things such as lectures or "fancier" meetup-style things; and I may go to some things that are completely casual but where jeans would look too casual.

In these situations, I'd like to feel confident that I look good, perhaps even attractive. (I would be dressing not only for simple social situations but for possible romantic situations as well.) The problem is that I've relied upon the above two styles of selections for so long that I'm really not sure what other ensembles I can put together, so I'm seeking advice here regarding same. Look at me and imagine I'm a caveman who just got unfrozen from Neanderthal times, and use very simple words with Grogg here regarding what type new-fangled-leopardskins Grogg should put on body that has ate too much mammoth-meat.

If it matters, I currently shave my head clean, but when my hair does grow in, it is a color between dark brown and black.

I do understand that spending more money allows you to purchase higher-quality garments that make you look much better. Money-conscious choices would be highly preferred, but if something's highly recommended enough, I can always put a bigger expense into my financial plans. I may not get to such a purchase for a while, however, as there are some financial goals I'm in the midst of working on.

I also understand that losing weight is one of the better ways to improve a man's appearance. I'm working on same, but, universally, nearly every weight loss article, book, or forum I have read instructs people: (a) not to hold off on making clothes purchases, or buy clothes too small for you, on the basis of anticipated weight loss; and (b) that making clothing selections that make you feel good in your current body can be highly beneficial to putting you in a better state of mind and confidence for said weight loss.
posted by WCityMike to Clothing, Beauty, & Fashion (27 answers total) 11 users marked this as a favorite
I'm not gonna get into the details, but the basic premise is: if you don't project physical power, then project social power. Look at how rich and powerful people dress and carry themselves. Especially old money, not nouveaux riches. Nobody cares that, undressed and unpainted, most of them are rather fat and ugly.

The "classic" look that everyone mentions but few can pull off is exactly what you want to go for. Wear a jacket and collared shirt with trousers, in all situations. Vary the materials according to the temperature / humidity, and the colours according to the occasion. And remember that 95% of good clothing selection is good fit and proportion, so as to flatter your body or draw attention away from it. Make sure the colours all match.
posted by randomstriker at 12:51 PM on May 23, 2008

I've answered this previously on MeFi and I think my advice fits, and would probably actually be taken, as I don't believe you mentioned any cape-wearing. Just say no to polos and Dockers.
posted by banannafish at 12:56 PM on May 23, 2008 [1 favorite]

Hey Mike!

I don't know how well this suits your budget or your personal style, but as a fella who's struggled with both his weight and how to dress himself, here's my thoughts on the matter:

Have you thought about trying to channel the style of some well-known big fellas? I always thought the Notorious B.I.G. looked pretty sharp in a suit. These were likely tailored for him, but I found the final effect quite flattering. You might also take a look at how Michael Clarke Duncan dressed for his role as the Kingpin in Daredevil. Don't try to minimize your size - take advantage of the imposing figure you're capable of cutting and run with it. Pick garments that exude power and presence.

It's hard not to feel confident in a flattering suit, and this is the course of action I'd recommend for you. I hearya on the lack of fashion knowledge, so why not talk it over with some professionals? Tailors and menswear vendors are trained to answer this very question - it might cost you a little coin and I understand how unpleasant a fitting can be for someone unhappy with his appearance (been there, too) - but think of these things as investments that will be well worth it if they add a little swagger to your step. There's really no way to put a price on confidence, or to undervalue it.
posted by EatTheWeek at 1:00 PM on May 23, 2008 [1 favorite]

Just one woman's perspective: I think men of all body types look great in crisply pressed oxford/dress shirts, especially in more interesting colors than bland old white or pale blue (I love medium-vivid greens, violets, and blues on men), coupled with dress slacks (no dockers!) or dark jeans.
posted by scody at 1:01 PM on May 23, 2008 [3 favorites]

Undervalue = overvalue. Oy.
posted by EatTheWeek at 1:02 PM on May 23, 2008

Oh, and also: since you wear glasses, don't underestimate the power of a really flattering pair of frames. (I know that new glasses can be pricey, so it doesn't have to be at the top of your list... but something to keep in mind.)

And by the way: good for you for deciding to expand your social boundaries! Best of luck, and have fun.
posted by scody at 1:06 PM on May 23, 2008

Response by poster: > Vary the materials according to the temperature / humidity, and the colours according to the occasion. And remember that 95% of good clothing selection is good fit and proportion, so as to flatter your body or draw attention away from it. Make sure the colours all match.

Just out of curiousity, can you (or anyone) point me to a website or source of information as to: (i) what material is good for what temperature/humidity, (ii) what colors are good for what occasions, and (iii) what colors match each other (my color-matching sense has always seemed a bit askew (although not wildly off)).

> Oh, and also: since you wear glasses, don't underestimate the power of a really flattering pair of frames. (I know that new glasses can be pricey, so it doesn't have to be at the top of your list... but something to keep in mind.)

*slight insecureness manifests* Are those frames unflattering? I actually got a lot of compliments after I purchased them last year, from a higher-end optician than I usually went to ...
posted by WCityMike at 1:07 PM on May 23, 2008

Are those frames unflattering?

No, I didn't mean that at all -- sorry! I just couldn't really tell how well they suit you (one way or another) from your profile pic, mainly because they're a light-colored metal frame. It was more a "I see you wear glasses, so make sure your frames are great!" observation. If other folks have given you compliments, that's a good sign.
posted by scody at 1:13 PM on May 23, 2008

I agree with scody. Crisp is good, often better than drapey fabrics that sometimes can be unflattering. And it can't be said too much that tailoring is your friend.

Good for you to realize that looking fabulous in your current body is the best idea. I recently made a similar decision and it has been much easier to lose weight and exercise since I can try to see myself as a "cute girl who needs to lose some pounds" instead of something less flattering!
posted by pointystick at 1:13 PM on May 23, 2008

I like banannafish's advice. I agree that a general laid back look, like J Crew or Banana Republic, are stylish, easy to pull off and will look good on anyone. You can probably get some similarly-styled stuff for cheaper at Target, so you may want to stock up on the basics there. Collared shirts and trousers - yes. But I would probably caution against tucking shirts in if you carry more weight around your midsection. I like the untucked shirt look on men and believe it can still look quite smart if worn the right way. Wear jeans, but buy nice pairs - like a boot cut with a darker wash, which will look more polished and may be more slimming. No light rinse. Gap probably has some nice ones. Don't wear tatty jeans that are ripped or overly faded.

Also, watch your posture. It may sound dumb, but if you slouch or have bad posture, you will undo any good work you do with nice clothes or weight loss. The good thing about being a man is that I think you can get away with carrying around a bit more extra weight than a woman could. Here are a few fashion tips for bigger guys.
posted by triggerfinger at 1:18 PM on May 23, 2008

I can't recommend much in terms of specific pieces, but I bet a casual blazer in a colour other than black* would carry you far. Something along these lines, but you probably don't need to spend that much, and I'm not necessarily suggesting you need to get like, that lapel or whatever, you kind of need to try stuff on to figure out what suits. Get a friend or salesperson to help if you're not sure about something. Also, what randomstriker said: fit and proportion are key, so try it on, and get it tailored to fit. The one I linked to is a cotton twill, so it's not like a suit jacket, but it can easily dress up a casual workish outfit for evening.

Also consider getting a couple of button-down shirts in patterns you like that you can do with or without the blazer; while you're at it, look into a couple of lightweight vnecks that you can layer over any collared shirt. Again, clothes that fit are key. A lot of men of all sizes make the mistake of wearing clothes that are too big, and that just makes you (anyone) look heavier.

Also, it sounds like you don't wear a lot of colour. That goes a long way in making the difference between dressing okay and having some style. I don't know what colours look good on you, but any clothing salesperson would. If you don't want to do, like a bright orange sweater (assuming orange looks good on you) because that sounds a bit clownish, a button-down with an orange stripe (or whatever) worn under a neutral blazer or vneck will still be more stylish than a uniform outfit of neutrals.

*Nothing against black, but it can look severe or formal. A charcoal grey or something brownish is probably better, depending on your colouring; especially if you tend to favour black pants.
posted by SoftRain at 1:21 PM on May 23, 2008

I would steer clear of places like Banana Republic, where the cuts of the fabric favor the slim. I'm an evenly distributed 30 lbs overweight and I can't wear their clothes any more and look good. When you are seeking a new look, a good bet is to head to a Bloomingdales or Nordstrom. You probably won't buy anything there because of the expense, but you have a wide variety of stylish clothing to try on and a very attentive staff that you can ask simple questions of like, "What line would you recommend for someone with my body shape and size?" From there, you can go to less pricey retailers and look for approximates.
posted by mrmojoflying at 1:30 PM on May 23, 2008

Get one nice suit, in charcoal, made for you. I would suggest a light wool. Get two pairs of pants with it. Buy shirts and ties based on their compatibility with THE SUIT. Bring someone along who is a decent dresser. You can wear the pants without the jacket if you want, but if you get them cleaned always take all three together so they fade evenly.

Wear an undershirt under your shirts, but make sure it doesn't pop out of the neck.

Get a thicker wool overcoat, in black, that fits you well and makes you feel awesome.

You don't have to be perfect. You won't know everything right away. If something makes you feel great, don't second guess yourself--wear it and enjoy.

Good luck!
posted by sondrialiac at 1:36 PM on May 23, 2008

Just out of curiousity, can you (or anyone) point me to a website or source of information as to: (i) what material is good for what temperature/humidity, (ii) what colors are good for what occasions, and (iii) what colors match each other (my color-matching sense has always seemed a bit askew (although not wildly off)).

I never had good fashion sense but I did develop an idea of what looks good together by looking at clothes, LOTS of clothes. What will help you get a sense of what looks good together is find a store that has clothes that you like and look at how they dress the mannequins in the window - how they put the outfits together. Also look at men's clothing store websites on the internet and see how they dress the models. This will give you an idea of what's fashionable, what colors look good toegther and you can kind of develop your own personal style from this, using your own preferences. Here's some more good tips.

On preview - I think Banana Republic may traditionally be cut on the slim side, but having just looked at their website, I discovered that they now have a big and tall section, with even more dressing tips!
posted by triggerfinger at 1:39 PM on May 23, 2008

This is not anything particularly plus size oriented, but it might help you figure some things out about clothes in general. The people who read and comment on this are totally obsessed with clothes. And you can kind of see what works and what doesn't.

I think no one said it, but I think pleats are generally not cool, if you can avoid them.
posted by sully75 at 1:47 PM on May 23, 2008

I'm definitely not an expert on fashion, but a few thoughts:
- Jeans are great for social occasions, but pick high end jeans. Look a "wash" (the color pattern) that is dark with a subtle vertical striping - it's both trendy and flattering.
- In general dark colors are more slimming
- Jackets are especially good when they draw a vertical line. An un-zipped, dark-colored jacket with a lighter-colored shirt is VERY flattering, especially in the evening. If you watch The Shield, they put the star Vic Mackey in leather jackets a lot in the later seasons.

FYI, a lot of department stores have very helpful personal shoppers. No fee, and they can be a big help in translating a specific desired effect into specific brands and items.
posted by CruiseSavvy at 1:53 PM on May 23, 2008

Mod note: This is a response from an anonymous commenter.

But I would probably caution against tucking shirts in if you carry more weight around your midsection.

This is the biggest problem for big guys with guts, I think...if you untuck, it just creates a tent-effect and looks like a muumuu. But tucking in has its own problems because big guys have two options when it comes to pants: 1) let your gut hang over the waistline of the pants, which makes it hard to keep 'em up and your shirt tucked in; or 2) buy pants that you can hike up over your gut to where your waist should be and cinch the belt down. Suspenders would be the natural solution, but who wears suspenders anymore? In either of the other two cases, tucking in your shirt is going to draw attention to your gut and your ill-fitting pants.

I don't know of any good solution, but here's two ways I deal with it:
- Wear a light weight sweater (like this) with a dress shirt or t-shirt underneath. Looks good with flat-front khakis and dress slacks. The fitted bottom of the sweater doesn't do the tent thing, but does cover your waistline.
- Wear a blazer whenever you tuck-in a dress shirt and wear your pants up at your waistline. I think the blazer makes for a more "put together" outfit than just a shirt and pants and helps distract from the gut.
posted by cortex (staff) at 2:01 PM on May 23, 2008

My advice is not about what to buy, but how to buy:

I do understand that spending more money allows you to purchase higher-quality garments that make you look much better. Money-conscious choices would be highly preferred

Even if you can buy three (low-end) x for the price of one (high-end) y, go with y. It means less clothing, but you'll probably end up with garments you are much happier with. Unfortunately, an emphasis on higher-end, quality garments matters so much more for plus-sized. Lower-end plus-sized clothing tends to be made of cheap fabrics that hang funny and often have some sheen to them. Not only do fabrics like this make it harder to wear interesting colors, but in any color, the overall result might be a less attractive, less classy or somewhat sloppy, cheap look.

If budget is a huge issue, my advice is to go to higher-end stores and try on lots of styles, note what looks and feels best, then comb tj maxx/marshalls/ross/etc. for those same brands and styles.

Also, when you try things on, sit down and stand back up. As dumb as you'll feel, simulate some of the motions you'll be doing while wearing the clothing (raise your hand, bend down to pick something up, go from sitting to standing a few times, etc.). Look at where your clothing creases and make sure that things don't ride-up too much, hang sloppily or bunch in the wrong places after some movement and creases.

Finally, when you are looking at yourself in the mirror, take a second to stop standing up straight and sucking it in and try to go back to a normal posture, even if it is a bad posture. This will give you an idea of how the clothing will look in your typical wear, because after you've relaxed a bit and started feeling comfortable, you'll probably forget to stand up straight and hold it in. If it is still comfortable and sharp-looking in your non-impress-the-mirror pose (everyone does this), then it is a keeper.
posted by necessitas at 2:01 PM on May 23, 2008 [1 favorite]

Even if you can buy three (low-end) x for the price of one (high-end) y, go with y.

Respectfully, I must disagree.

Aside from choosing materials for comfort and climate (which is sometimes expensive), my thinking is that it doesn't matter how much each individual piece costs. What matters is how well the whole package is put together. Some of my favourite items are from the bargain bin or from a thrift store, and made from some really cheap material. But they go well with the other things in my wardrobe, and I look great in them.

Unfortunately this takes time, effort and a good eye. Consequently, if you want to dress well, you have to enjoy dressing well. Don't look at it as a chore or as something you need to do to impress others. Dressing well has to be an enjoyable end in itself, to impress yourself. You need to develop a fashion sense, which will take time. Read some men's magazines -- don't buy a whole tonne right away but rather flip through them once a month or so, EVERY month.

OK, now that I'm on my lunch break, here's a few specific reccomendations:

Best book I've ever read: Color for men. Out of print but available second hand.

Best one-stop-shopping destination for the "classic look": Brooks Brothers

Must have items:
1) Black jacket
2) Grey striped jacket
3) Brown corduroy jacket

Start with these and wear at least one of them ALL THE TIME. Build your wardrobe using these as the base. Make sure they fit you very well. When you shop, always think of how your purchase will match or complement your base items.
posted by randomstriker at 2:30 PM on May 23, 2008

This may sound intimidating but I think seeing a personal shopper at Nordstrom's in Chicago could be really eye-opening.

I had to learn how to dress in a way that is flattering and pick out good quality, well fitting clothes. One of my roommates in college was studying to be a fashion designer. I couldn't afford the clothes that she loved. But trying some of them on when she took me shopping and having her explain to me WHY something looked good on me or didn't look good was an amazing education for me. Now, I'm able to pull something off of a sale rack that I know will work for me and I'll know it's a deal because I understand what makes something well made and lasting. I learned what to look for and how to find that look in shops where I could afford the merchandise. I also learned when it was worth it to pay more for something. I have this absolutely classic dress coat that I bought in 1991 that still gets amazing compliments. I've had it relined at least once. It cost $400 on sale in '91 (a small fortune then for me) but I've had it for SEVENTEEN YEARS. It's never gone out of style. So I've invested $23 a year so far in a coat that I love to wear.

Having a session with a personal shopper at Nordstrom's would be like taking a class in what looks good on you. They can also explain how using a tailor can really change the fit of something dramatically. Even if you only buy 1 thing (or nothing, but be sure to tip them handsomely...hey, it's tuition!), you will have the knowledge you need to look at clothes sold in more affordable stores with a critical eye.
posted by jeanmari at 2:54 PM on May 23, 2008 [1 favorite]

I think you may be able to rock a Guayabera - it's not for everyone, but when it works - ain't no snazzier!

here's some better examples than that wikipedia picture
posted by jammy at 5:11 PM on May 23, 2008

Having lived with and loved a couple of big men, I can tell you what I like. Dark jeans, retro looking shirts (Guayabera!) over a t-shirt, but not tucked in, and a tailored jacket. Seriously, sink some cash into a great jacket that's altered to fit you precisely. You'll get a lot of mileage out of it.

As for places to shop... Men's Warehouse carries a great range of sizes in store, and can help you find a jacket that looks great. They also do alterations on sight. Target is great for basic shirts. Crazy old man catalogs like Haband will have a few awesome shirts in large sizes. And for the classics, go with Ralph Lauren who has one of the better Big and Tall selections (but is only available online, I believe).
posted by kimdog at 5:26 PM on May 23, 2008

I totally second those Guayabera shirts for big guys. Actually, I think they look good on most guys. That look is hot. Or something in the cut of a Tommy Bahamas shirt, but in solid colors, or with a very, very muted design (not the tropical look). I think the shirts that are tucked into pants don't look as good on bigger guys (or women).
posted by gt2 at 7:32 PM on May 23, 2008

Don't be afraid to try suspenders. Especially if you wear them under a jacket. They really are the best way to solve the belly-over-waistband problem.
posted by bingo at 7:38 PM on May 23, 2008

For heavy men, it's all about the vest/waistcoat (definitely for formal, maybe for semi-formal as well if you can work it).

They look great on all men, but they seriously flatter large men. Basically, they put darker colours around the middle, which makes it look narrower, while leaving the brighter shirt visible near the neck - and on the shoulders if you end up removing your jacket, and shapes your whole torso. I have a friend who is fairly heavy, but when he wears his dinner jacket with a waistcoat, it's like he shed 20 pounds. The example I linked to is a little old fashioned, but kind of funky looking - but the key is dark, rather than bright - NEVER wear a bright waistcoat with a dark shirt.

(I really wish the waistcoat would make more a comeback - I was watching tv the other day, and seeing how an otherwise skinny man looked like he had a huge paunch just because his shirt was blousing too much over his trousers. It used to be that a man was considered somewhat undressed just wearing a shirt.)

Other general principle: neatness. I'm saying this as someone who is also heavy, from a family which is heavy, but one of the worst stereotypes of overweight people is that we just aren't as fastidious as other people. It does not help that a lot of plus size clothing is very badly tailored. You have to work against this, and go for always more neat, pressed, and tailored look than a thin man. If your trousers slip down, absolutely wear suspenders - hide them under a waistcoat if you think they don't look good on you. (Suspenders/braces can be very flattering to a point, as the acentuate the shoulder line of men - think Captain Jack from Torchwood. But if they can also accentuate the middle. Generally if your shoulders are the same width as your waist or wider, they will flatter; if your waist is wider, they won't, and you may want to wear a waistcoat over them. I'm speaking from experience - my husband and my grandfather both wear/wore suspenders all the time.)

Have nicely fitted pants/trousers, pressed shirts. Also go for button up shirts with a collar, pressed for good occasions -- only athletes look good in t-shirts. The rest of the male population all look better in nice collared shirts - and woven is better than knit.

I think you should go for a slightly old-fashioned but not quite dandy look, if that at all appeals to your taste - suits or jackets with waistcoats, nice ties, button-up shirts with collars, nice shoes. How do you look in a fedora? Don't worry about being over dressed - while being under-dressed is a faux pas, being slightly over dressed is an interesting affectation, and attracts good attention. I've seen this pulled off extremely well, in varying styles - forties-esque, or Edwardian or even Oscar Wilde like.

You know what is a real shame? There ought to be more fashion stuff for men out there, talking about what looks best on average men. (I have lots of ideas about how to dress men better - maybe I should start a magazine :)
posted by jb at 9:39 AM on May 24, 2008

This is the biggest problem for big guys with guts, I think...if you untuck, it just creates a tent-effect and looks like a muumuu. But tucking in has its own problems ...

Even moderately plump women have the same problem -- and again, I would point out that the waistcoat/vest solves this problem. No tuck/not-tuck dilemna!

If you are worried that a waistcoat alone would look too much like, Oh, he's overweight and trying to cover it up, just pair it with a jacket. Most people probably won't even think about the waistcoat, just see the overall ensemble.
posted by jb at 9:52 AM on May 24, 2008

Layer on the upper body - a wifebeater / undershirt, a v-necked t-shirt, a jacket; a t-shirt, a light, thin v-neck sweater, a jacket. Tuck in the layers underneath, leave the rest out. Layer similar colours, lightest lowest. Stick with v-necks and open, large collars - you don't want fabric against your neck unless it's a very good tie with a generous knot.

If you're not layering, use well-weighted fabrics and a tailored rather than stretch fit. Heavy cotton, single colour but textured business shirts, structured collars, French cuffs, a big watch, good boots, thick ties tied well. If the temperature permits, always wear an undershirt.

Avoid polos if casual - go for a light, plain v-neck over a patterned collared shirt with generous cuffs that show under the sweater's sleeves.

Do not wear pants with more than one pleat. Slacks should be wool-blend, single pleat, a crisp seam with enough drape to cover your sock line when seated, but not enough that it's billowy. Jeans should be darker indigo with faded fronts and backs and a generous boot cut - check the length. Get two nice plain leather belts - one brown, one black - with a large, clean steel buckle.
posted by obiwanwasabi at 4:47 AM on May 26, 2008

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