MeFi Eye for the Dork Guy
April 12, 2008 10:23 AM   Subscribe

I'm a heavyset, geeky guy with no sense of fashion or style. Can you help me change my look?

I'm about to graduate college and be thrust out into the real world. I'd like to change my appearance a bit (or more than) to look a) more professional, b) more attractive, and c) less clueless.

I'm already aware that I should try and lose some weight. I'm gonna work on that. What I would like to know is twofold:

1) What should I do w/r/t clothing? Right now, my usual wardrobe is a pair of jeans (black or blue), an untucked button-down shirt (often black), or a t-shirt (often black). Recently, I got a nice charcoal gray blazer, which looks wonderful. Aside from more colors—and my preference goes towards dark colors, I don't plan to change that—, what else should I be considering?

2) What should I do with my hair? Currently, I wear it long and in a ponytail. I have a very round face, and very, VERY, fair eyebrows. Short hair, such as buzz-cuts or the like, tend to make me look like an overgrown child. Also, I have a whole fuckload of cowlicks, and I don't want to spend an hour preening my hair to get it together each day. I'm absolutely lost about what to do with my hair to make it look sane. Any suggestions would be appriciated.

Here is a photo of myself for reference. I don't have a full beard anymore, but everything else is pretty accurate.
posted by SansPoint to Clothing, Beauty, & Fashion (31 answers total) 17 users marked this as a favorite
Best answer: #1, it sounds like you have a decent foundation. Make sure the jeans you have look modern- I personally don't find black jeans on men a particularly modern look, but I suppose it's possible I've just never seen a really nice pair. Are your jeans relatively new and free of tears? Not too wide and not too narrow (think boot cut)? Hemmed to the correct length? Think on these things. Try different shirt styles- wear polo shirts, tucked-in button down shirts, crew neck shirts with the blazer or other light outer layers (sweaters). If you're going to wear a t-shirt, don't just wear a plain colored t-shirt, wear a t-shirt for your favorite band, city, sports team, internet website. Make sure the t-shirt fits you well; only circus elephants look good in tents.

#2, Do you have a male friend who has great hair? If so, ask who cuts it. Their stylist could probably help you find a style that will look great and be easy to care for.
posted by ThePinkSuperhero at 10:31 AM on April 12, 2008 [1 favorite]

If you're going to wear a t-shirt, don't just wear a plain colored t-shirt, wear a t-shirt for your favorite band, city, sports team, internet website.

The poster says he wants to look more professional. I don't think logo t-shirts are going to make him look more professional.
posted by jayder at 10:35 AM on April 12, 2008

1) Avoid pleated pants at all costs. They draw unwanted attention to unflattering areas.

2) Cut the ponytail. Only philosophy professors can pull that look off.
posted by Ugh at 10:43 AM on April 12, 2008

I would say you should lose the ponytail because when you pull your hair back like that it accentuates the roundness of your face. You don't have to go super-short though. I have a friend who went from ponytail to about a chin-length cut. His hair is fairly thick and wavy so it does its own thing and I doubt he puts any product in it. If yours is fine in texture, you might have to put some gel in but it shouldn't be a big deal. It's not super-neat but it's nice enough for business purposes, and he's a manager type.

Check out these "long" hairstyles. The first one is something like my friend's cut. I am not saying it's the cut you should definitely get, but it's just to show some options that are between ponytail and buzz cut.

As far as getting the cut, you should go to a good salon for it, not Supercuts or the neighborhood barber. If you can find someone who comes highly recommended (try citysearch or yelp for your city, or ask a female friend with great hair) you should be able to put yourself into their hands and they will help you find a look that works. Once you have a look you like, take some pictures so you can remember what it looked like.
posted by cabingirl at 10:50 AM on April 12, 2008 [2 favorites]

Best answer: Cut your hair. I too am an overweight guy with a boyish round face, so I understand your fear of looking like a child. But look around at the other overweight people you see with unusual hairstyles. The hair always looks ridiculous, like they are trying too hard to distract from their chubbiness. Ditto heavy people with crazy hair colors, lots of piercings, tattoos, etc. The most basic prejudice that people will have against you because of your weight is that you're sloppy. The best way to fight that prejudice is to keep the rest of your appearance neat.

That said, a buzz-cut is of course too much. Go to a stylist whose work you have seen, and trust them a little.
posted by bingo at 10:50 AM on April 12, 2008 [1 favorite]

Best answer: Are you looking for more of a grownup/stylish look in general, or are you more concerned with looking businesslike for the career world? The reason I ask is that answers for the latter will vary depending on what field you're going into.

If you want some style tips in general, I agree with the suggestion that you seek out advice from a good hair salon, one that is likely to serve a stylish male clientele. They could probably help you out with a shorter (mid-length?) cut that would add a little volume, which would probably balance out the roundness of your face, and that was fairly easy to maintain with a product or two.

You might also consider updating your glasses. I can't see the ones you're wearing that clearly in the picture, but they look like narrow wire-rims? Maybe something with a little more definition would add some style (and also draw attention away from the fair eyebrows a bit).

Making sure your jeans are current is a good idea, and maybe adapting some more funky blazers/jackets in general is a good idea. Not sure what your budget is, but my husband, who's also heavier set with very broad shoulders, had pretty good luck at Macy's. I'm not a fashionista by any means but I'd think a cool blazer, a non-bulky T-shirt or knit top (relatively fitted, not with a specific band/team logo but maybe more of a cool design, well-fitting jeans, and cool shoes -- a good store can direct you to all these things -- would be a good, grownup but not old, look.
posted by justonegirl at 10:52 AM on April 12, 2008 [1 favorite]

Response by poster: Check out these "long" hairstyles. The first one is something like my friend's cut. I am not saying it's the cut you should definitely get, but it's just to show some options that are between ponytail and buzz cut.

Dear lord, it's like I fell into a timewarp back to the 1970s. That's frightening!
posted by SansPoint at 10:53 AM on April 12, 2008

#1. It's good that you are thinking about clothing now rather than falling into the trap of "I'll buy new clothes once I lose five pounds". If you're going to thrust yourself into the outdoors, you need to dress the body you have now. If you do lose weight, you can always buy/tailor/invest in new outfits. But coming up with some decent style can come about with any body type.

Check out or buy Dress Your Best. It is by the two hosts of What Not To Wear. The book consists of some good simple instructions and lots of pictures of different body types (the first 2/3 is mostly for women but they actually DO talk about dudes for the last 1/3) and it'll give you some good ideas on what to own and how to dress. Even though the fashion media market is heavily female oriented, there are still some good things out there for dudes.

You are right in that you need to add more color into your warddrobe. You have pale, redish skin which, to me, thinks that darker colors probably work best for you. Dark blues, greens, browns, and pinks are probably going to work best with you (though that picture of you could just be flashed out so I dunno). Colors are great but the thing is, you need to find pieces that fit. That's the key.

For a shirt, it should not be too long. If you're buying xxl, make sure it's because you really are xxl and not because you're trying to hide yourself in your clothes. Try different sizes of shirts on. A good shirt will be only slightly longer than your torso and will feel snug on your shoulders and your biceps. Since you currently buy a lot of button down shirts, make sure you're buying the right size and make sure you've been sized correctly. Buy different styles of shirts though. Polos and anything with a collar should have a short collar - it should elogate your neck without making you look like a turtle. If you want to bring more trend to your life, look around for stores like Express or Forever 21 or H&M or urban outfitters. T shirts, for men, are always in style but it seems that the current trend is with skulls, elaborate patterns. Move away from the threadless or dorky tshirts and instead move on to more general and trendy looks.

Now, with pants, fit is also key. Make sure that the length is tailored exactly. Do not roll your jeans up - that isn't cool. Pay the 10 bucks, get to know a good tailor, and get your pants hemmed. For jeans, a dark wash denim is the prefered "professional" look right now. If you go to stores, you'll notice that dark denims, while popular, are starting to lose out to a lighter wash (ala late 80s/early 90s). I personally prefer the darker denim and if you plan on wanting to appear "professional" or wear jeans in an elegant/business casual setting, then go for a dark denim. When it comes to khaki style pants DO NOT GET PLEATED PANTS. I can't stress that enough. It will add extra fabric and weight to you. Go for pants with flat fronts. Darker browns and blacks will work best for you. Stay away from light khaki unless you want to appear like you're 40 and a mid level manager.

For your feet, stop wearing white socks - switch to black or silver or whatever - just stop wearing white atheltic socks. Move away from atheltic sneakers and instead try for shoes that are a little more hip, different, and will elogate your legs without making it appear as if you are going to stomp on someone.

Oh, and one more thing, if you're going to wear button down shirts, iron iron iron. Wrinkles on clothes are very unsexy and make you look less put together than you really are. Keep your clothes without tears, clean, and unfaded. If something gets old, toss it. Don't get emotionally attached to your clothes or else you'll be the guy with the sweatshirt that is full of holes but you can't get rid of it because "it's a part of you". Bah. Nix that attitude stat!

#2. Now, for hair, I agree with TPS - go to a male stylist. They'll be able to help you come out with the right look. You're going to probably end up cutting it short but a stylist will be able to come up with the look that will fit your face and make you look great.
posted by Stynxno at 10:57 AM on April 12, 2008 [1 favorite]

Best answer: OK, get thyself to the mall. If you're focusing on a more professional look, I would recommend Banana Republic and Express as a start. They're not perfect, but anything there will be an improvement. More importantly, take advantage of the salespeople. Find one who seems helpful and explain your situation and the fact that you are "clueless" when it comes to fashion. Don't be intimidated. They will be more than happy to help you find combinations that look decent, considering that they want nothing more than to sell you clothes. The fact that they work there generally means they have at least some understanding of basic fashion.

As far as your hair, you've got to get rid of the ponytail. Not only does it look unprofessional, the ponytail hasn't been in style for 20 years, it not longer. As someone said above, find a good stylist who can give you personalized recommendations. I would consider putting some blond highlights into your hair, which would be a nice mix with the reddish tone you have now. In general, your hair needs to be less "flat" and cut into some kind of shorter style that you're comfortable maintaining yourself. The fact that you have fair eyebrows and skin is not a problem, although you could certainly have your eyebrows dyed, which is not entirely uncommon for men to do nowadays. Also, try a different style of glasses or switch to contacts. The ones in the picture aren't really doing you any favors.

Lastly, I would lose the facial hair entirely as it's not helping anything. But if you do like it, a goatee might be a good option for you. Just make sure you're able to keep it well groomed, particularly if you're going to be in professional environments.

Good luck. Don't be intimidated, and don't be afraid to try new things. The fact that you recognized that you needed help is very positive. Remember that you're not a lost cause. :)
posted by iamisaid at 10:57 AM on April 12, 2008

Best answer: All you need is a haircut. If you are on the heavier side then jeans/trousers and a button down shirt is perfect. Treat yourself to a variety of shirts in subdued, pastel colours, a variety of trousers and at least a couple of smart white shirts and black trousers. A blazer and/or a suit jacket and you have the basis for a smart working wardrobe.

Hair - you need to cut it. Pick a nice hairdresser, not just the local barber. Explain your concerns. Take them in a photo of a guy with a short, modern, businesslike haircut - Brad Pitt, Matt Damon or the like - seriously. Get it cut in a neat, tidy cut. Ask for it "choppy" or layered on the top, and explain that you'd like to be able to get up in the morning, run a brush over it a couple times with a tiny bit of gel or whatever, and be out the door. They should understand perfectly what you mean. You'll find a short, tidy haircut far easier to deal with than what you have now. Without sounding harsh, your hair at the moment is only going to detract from whatever effort you are putting into your new clothes. Sad to say that long hair pulled into a ponytail on a guy will immediately pigeonhole you in all sorts of ways.
posted by fire&wings at 11:00 AM on April 12, 2008

It'll be hard to answer this question without sparking a sanctimonious flamewar given everybody's different standards and opinions and selling-out aversions. So let's all breathe evenly and remember that he asked.

With that said, it sort of depends on what direction you're heading. Are you headed towards a professional setting? An artsy/creative setting? A service setting? A trade setting? A freelance tech setting? Depending on which one you pick, you wouldn't necessarily need to change anything, though I hear that you'd like to, and that a professional look is a specific goal.

For professional, I'd say you'd want to do a few things. Firstly, it's time to lose the ponytail. Nobody likes a lot of hair maintenance but the ponytail will be substantial unspoken or subconscious points against you in most professional situations, especially at the interview stage. (If professional of the tech variety, points are forgiven). Have a ceremony where you cut it off an leave it behind you with your other youthful castoffs. You don't necessarily have to go buzzcut, but you'll want a generally clean look. Good move on the facial hair. It'll be a good idea to keep that clean. You may also want to upgrade from jeans to khakis, or the darkly-colored equivalent of your choice. Jeans are fine for home and the weekends, but regular pants will start coming in handy more frequently now. And that means your shoes need to upgrade to match.

Have you considered different glasses? It may just be the photo but I think what I'm seeing is a bit of tint, no anti-reflective coating, and full frame rims. You can really change your look with some minimalized or absent rims, zero tint, and ARC. You might experiment with some different lens shapes too. The ones I'm seeing on you are constricting and restricting access to your eyes. If you have your prescription, you can do this all very cheaply at Zenni Optical. $8.00 glasses! You could get a few.

I disagree with pinksuperhero on the tees. If your goal is to look more adult, plain understated tees would do that better than tees advertising sports teams or bands in my opinion. If plain is too boring for you, there's always the hipster route, with ironic whatever on the front. But again we're talking casual wear with any tee.

A watch could further professionalize your look. It does't have to be expensive at all. Just metal, pretty much, preferably analog not digital. No plastic bands and no calculator buttons.

On preview I see others are way ahead of me on a number of points so I'll stop. Good luck man! Look sharp.
posted by kookoobirdz at 11:09 AM on April 12, 2008

Best answer: It looks like you have fine hair, which would benefit from a really good professional cut, not a buzz, but layers. Get some referrals from friends for a good stylist: it's worth the money. Tell them you want something that's easy to take care of, but you may have to use some product, like a good hair creme, to keep the cowlicks/fly-a-ways under control. That only takes a minute to add after a shower and toweling dry.

Clothes: don't just limit yourself to black and dark colors. Check out this site for more varieties suited to you and fashion tips for men.

Visit one of the finer department stores and get thee a rep to help you pick out some nice slacks and shirts, with coordinating ties. If you can't afford that, go to Burlington Coat Factory or Kohls, BCF has great deals if you hunt. I'd avoid pants with cuffs, as those can add to the weight look (I avoid them myself). Get two-three pair of black and/or charcoal grey slacks, and a really good quality belt. Pick out 7 dress shirts in varying colors and ask people (a friend who's a girl or the clerk) which color looks good next to your skin tone. For instance, if I wear yellow, I look horrible, but certain shades of yellow are okay due to their tone. You'd probably do well with a slightly dark sage green, as well as a variety of other colors. Look at Clinton Kelly on TLC's What Not to Wear, Tim Gunn's Guide to Style on Bravo (Tim Gunn, not the girls), and men's magazines. Pick something just a little outside of your comfort zone and try it.

Also, stay away from really wide ties with big stripes. Look for single-colored ties or ties with small patterns.

Invest in a good pair of shoes, like Rockports and some nice dress socks in neutral colors like black and grey. Good luck!
posted by Marie Mon Dieu at 11:13 AM on April 12, 2008 [1 favorite]

Yeah, cut your hair and keep shaving. No one cares if you look 'boyish' and in a few years you'll be happy for it. Good advice all around here.

I second Banana Republic. It's sort of expensive, but in my experience, it's well made and lasts a long time. Simple, understated modern stuff that I don't have to think about.
posted by jeff-o-matic at 11:16 AM on April 12, 2008

Also just want to say that it's ballsy of you to post a pic and invite critique. You go, buddy.

Oh, and on the shoes, I'd aim for leather, classic, and understated. I'm all for dark brown given that it goes with more than black does. Gotta have black for any black pants though.
posted by kookoobirdz at 11:17 AM on April 12, 2008 [1 favorite]

Also, go to the biggest Banana Republic near you and go directly to their sale section. Just shop there. It cuts down on having to choose from a million different things and it's cheaper. Stop in every month or two and you'll soon have a decent sized wardrobe.
posted by jeff-o-matic at 11:18 AM on April 12, 2008

Response by poster: Marie Mon Dieu: "Visit one of the finer department stores and get thee a rep to help you pick out some nice slacks and shirts, with coordinating ties. If you can't afford that, go to Burlington Coat Factory or Kohls, BCF has great deals if you hunt."

Preach it. BCF's where I got my blazer.
posted by SansPoint at 11:28 AM on April 12, 2008

Best answer: Sans, my 2¢.

1. New glasses are a must. They're like a t-shirt that YOU NEVER TAKE OFF. You don't have to spend a ridiculous amount but definitely start shopping. Try on a lot of things and you'll start to see things you'll like. Since your face is round, you can go for some more angular glasses (rectangles).

2. Cut the hair. Go for the mussed look or something else that is not too buzzed and not *too* old. You're a young guy, so get a cut at a place

3. Layer layer layer. The blazer is a great start. You could get another. Or a lightweight summer jacket (casual), like a shirt jacket or even some kind of dressed up track-type jacket. This, over a t-shirt or polo would be great for hanging out for a beer on a weekend afternoon. Or for work. Another layering point is to wear undershirts. Even under your cool tshirts, or a polo.

4. Consider pants. Pants are not jeans. They're khaki's (in a dark color) or cords on the casual end and then you can also get a pair or two pairs of real pants (wool). These look clean and grown up and will run you between $60 and $150 a pair. Try some things on at J. Crew, Banana Republic, and French Connection. Some higher end brands that are often discounted are Polo, Theory, and Modern Amusement. You can find some of these brands at places like TJ Max, Marshall's and outlet malls. But I'd do some looking first at a regular-priced mall to find what you like and what looks good on you. You might feel silly doing this -- I did (I bought my first pair of nice pants late in college, right before I cut my long scraggly hair). But just say something to the employee like "I've got a job, so I want to update my wardrobe" and they'll fall all over themselves trying to help you buy shit. But don't feel pressured. Say you want to try on a bunch of stuff and see how it looks. Tell them that you still need to go back in for another interview and that you don't know what poeple are wearing so that you HAVE to wait. But definitely try on some things.

Oh, and about pants. MAKE SURE they're long enough. Make sure they "break" in the right place; they should form a slight pile on top of you shoes. You should not see your socks as you walk. But get some dark socks too.

5. Shoes. Get some good looking shoes that are not tennis shoes. This will make you immediately stand out to employers and to ladies you want to impress. You really need 2 pair: 1 dressy pair and a casual pair. The dressy pair should be black, since you like black and will probably buy black pants and cords. Keep 'em shined and conditioned. The casual pair could also be black but should be some of those "fake tennis shoes," like those made by camper (expensive!), sketchers (cheaper), or steve maden (mid-range). The'll have some sporty stuff on 'em (stripes and the like) and will have black laces. One way to make them more casual is to go with a brown color, but since you're digging black, I'd stay with it.
posted by zpousman at 11:34 AM on April 12, 2008 [2 favorites]

I like the goatee, actually, but I agree that you need a new, shorter haircut. Rectangular heavy-ish black eyeglasses would look great. Get a few more blazers, they are super-versatile and look very professional.
posted by miss tea at 11:44 AM on April 12, 2008

I think you're a cutie. I'd hit on you. If I were pressed to suggest changes, there's only two things I can think of: The button-down shirt is a good look for you, but that colour is so bland. Some more vibrant colours would bring your face out more.

Let your hair down! Long hair is so sexy, but you kept it hidden. Also, it looks a little frizzy. If you're going to have long hair, I'd recommend taking better care of it. Condition every day and make sure you know how to brush or comb correctly. When you brush or comb, start from the bottom and work your way up. You shouldn't brush with forceful strokes, because it breaks the hair.

You've probably heard this before, but it bears repeating: You don't "need" to lose weight. Lose weight if it makes you feel good, but don't by any means think it's a necessity.
posted by giggleknickers at 12:03 PM on April 12, 2008

I'd like to add something. After looking through your Flickr photos, I've seen how you look in more vibrant colours. I agree that you look great, but the problem is that your hair and face are sandy colours and so your face looks washed out next to the pronounced colours of your clothes. This could be fixed quite easily by getting glasses that are rimmed with a more pronounced colour. Black would probably clash with your warm colouring, but you'd be a knockout in some charcoal-rimmed glasses.

I also want to add that it's very easy to tame cowlicks with a little hair serum. Just smooth a little on your hair before you brush or comb it. Pantene Pro-V Smooth and Shine is excellent. No hairstyling skill is required, just don't use too much or your hair will look greasy.
posted by giggleknickers at 12:16 PM on April 12, 2008

I hate to be the one to say this, but no one else has yet. Some heavyset guys (and I'm sure some skinny ones) tend to sweat a lot. Do whatever is necessary to avoid pit stains. Also, ask a friend you trust to critique your scent. Apply deodorant/cologne as needed. Avoid shit like Axe body spray.
posted by desjardins at 12:53 PM on April 12, 2008

oh, and you're not going to like this, but the hat in your Flickr photostream is not doing you any favors, in part because it's round and your face is round, but also because it's a hat with a suit and only Cary Grant can pull that off. The shirt/tie rocks, however.
posted by desjardins at 12:57 PM on April 12, 2008

Best answer: Just wanted to chime in that I think you're cute, too. Don't worry too much about losing weight; as long as you have clothes that fit you right, you're fine.

Points mentioned above that I agree with:
--no pleated pants
--dark jeans, but not black
--the charcoal blazer sounds very nice
--logo t-shirts are fun, but not terribly professional. Black t-shirts are classic. Stick with that. Stay away from white.
--don't wear sneakers, moccasins, or white socks
--cool, interesting shoes go a long way toward making you look more stylish. Born makes great ones that are also insanely comfortable.
--do cut your hair, and if it's not too fine, an intentionally messy style is great and easy to do
--accept the fact that you may need your clothes altered a bit, and do it.
--Make sure your pants aren't too short!
--stronger, angular glasses would be totally hot

Things I'm not sure were mentioned yet:
--always wear an undershirt with button-downs--looks much more put-together
--for slacks, dark gray is better than black (too waitery) or khaki (too boring; not flattering)
--striped shirts can be nice but the stripes shouldn't be more than about a millimeter wide, otherwise you'll look clownish or like Garth Brooks
--don't wear a tie unless you absolutely have to--they don't especially flatter larger men--but if you do, make sure you have a shirt with a collar that really fits you.
--avoid short-sleeved button-downs. If it's hot, wear a t-shirt or polo.
posted by exceptinsects at 12:58 PM on April 12, 2008

Short hair might make you look like an overgrown child but long hair and patchy facial scruff just makes dorky men look like the comic book guy. Pay a hair stylist 50 dollars and lose all the facial hair. I once thought it added a degree of definition to my round face as well, but it just made it look like I had a wreath of fur around my head. The only way I managed to add any definition to the lower half of my face was by losing weight.

Go for big chunky Elvis Costello style frames.

Pants and shoes make more of a difference than you'd think. Raiding thrift stores for old man pants and Wal Mart and Target for cheap but decent matching shoes will give you a solid lower half wardrobe for well less than $200 and that will keep you set until you're ready to invest in wool pants and Italian shoes. Throw out every pair of shitty brown hiking boots you have. Before you put anything on, ask yourself if you'd see this article of clothing in a server room. If so, lose it or layer it.
posted by bunnytricks at 1:43 PM on April 12, 2008 [3 favorites]

I was going to say exactly what bunnytricks said about the Costello frames. I would add that if you check out, you'll find that you can do it for much less than you think. I got me some chunky frames for $35, and I'm wearing them right now.
posted by 4ster at 3:16 PM on April 12, 2008

Everyone's saying your hair needs more volume. It doesn't. It's not a round head that is unflattering, but a round face. Pulling your hair back makes your face look as round as it can possibly be. It's not a major problem (it's arguably not a problem at all) and it can be fixed very easily. Solution: Side-sweep. Your hair needs to cut into your face so it's not just a big circle.

And nthing the "big chunky Elvis Costello style frames." Think you could pull off a Hodgman?
posted by Sys Rq at 5:00 PM on April 12, 2008

I would suggest taking a few of your more stylish friends to the mall or downtown for a bit of shopping. Be open to their suggestions and try on things even if you don't think they will work. Ignore prices at first and don't buy anything the first day, instead create a running list of particular garments that your friends think look great on you. Once you get a rough guess at what you want to purchase try to work everything into list of items that coordinate. Once you have your list return to the mall and try to find the items on your list that fit your budget. The web and thrift stores can be very helpful for this.
posted by kscottz at 5:02 PM on April 12, 2008

I think this Hodgman just might be sporting my next haircut.
posted by bunnytricks at 5:21 PM on April 12, 2008

As others have said, cut your hair. I'll add shave your face. Few things go as far to make a guy look sharper than a good shave, imo. As one of my female friends says, "Nothing says 'I can barely dress myself' like sculpted facial hair; it's the last refuge of the unfashionable man."

The absolute best fashion thing I've ever done was STOP wearing denim of any kind. Shirt, pants, whatever. And when I say denim I mean jeans of any kind, chords of any kind, any pleated pants, khakis or basically anything you can buy at a chain store like the Gap or Old Navy. Those clothes make you feel fat. At least they did for me.

Find some stores in your area that are not chains and specialize in men's clothes. Start by buying yourself some comfortable and fashionable pants. After a couple months of this you'll find that the shirts, glasses, and everything else you wear will follow in kind. By that I mean once you realize how much better and comfortable you feel in quality pants, you'll switch to better everything else.

Depending on your budget, also invest in some quality shoes and glasses. My favorite shoes are Cydwoq (though they almost always look like shit in photos--I get a gazillion compliments on mine; I have 7 different pairs and prefer the flats to the two-tiered soles). When you're ready for new glasses, don't go to the mall or one-hour frame places--find a place that specializes in designer frames, go there, and buy the least outrageous frames they have and you should be a cut above everyone else without drawing too much attention to yourself.

Hunt around for a quality used men's clothing store. For instance, in Toronto, I frequent Off the Cuff, which is a reseller of high-end men's clothing (ie, name brand designer clothes, nothing older than 2 years). Their web site is atrocious but the store has great clothes. I'm sure any major city would have a similar outlet.
posted by dobbs at 8:19 PM on April 12, 2008

Find a friend with a sense of style you admire or that you hear other people admiring, and ask that person to be totally honest in their critique.

Also, be willing to let go of some things:
the long hair will stand in the way of job success, and unless you're one of those rock-star guys with a career where long hair is part of your appearance (I'm guessing not) then lose it. There are still a lot of conservative employers out there.

If you have a monobrow, suck it up and pluck no matter how metrosexual that may seem. Controlled facial hair suggests self-discipline.

Tuck in your shirts - ALL of your shirts, always.

Invest in two belts, one black, and one brown. Also make sure you have two pairs of shoes that are also black and brown; these shoes should be decent quality. Men aren't as conscious about it as women are, but there is a weird social language wherein we are judged by our shoes. Don't wear the brown with the grey blazer.

Make sure your clothing fits you properly - buy a measuring tape and get comfortable with it. When clothing shopping, you should go for clothing that is two inches larger than your measurements, because the measurements of the clothing is a measurement of the fabric, not of the size of the person intended to wear it. If you're heavyset, then JC Penney's is a great place to go for larger men's clothing. It's pretty affordable, and the quality is decent if you take care of your clothing properly.

Make sure that the length of the pants is also appropriate - if you need to, buy a pair that are a little long and find a tailor to alter it, or if you're hardcore diy, hemming your own pants is a great skill to have for men or women.

Beauty products not to fear:
Razors (OK, a little, but you probably live with it already)
Aloe (more manly than moisturizer)
Whitening strips
Manicure tools - a nail clipper and file, really, maybe a stick to dig out nail gunk(some employers do check your manicure as an indicator of your attention to detail)
Lip balm
Any clipper for removing excess hair where hair really shouldn't be able to grow

Once you get comfortable with the blazer, etc. consider adding some color anyway. While the monochromatic/dark colors look is one of the easiest ways for men to dress, only Seth Green has managed to pull off the monochromatic look in Geek Chic well, and even he gets dissed for it. You don't need to do that much, just add a colored shirt. But avoid patterns for professional looks - it's a rookie mistake.
posted by medea42 at 9:29 AM on April 13, 2008

*darker pants (no khakis, those don't look good on anyone)----even gray is better than beige/khaki, especially on heavier people. these are about as light as I would recommend you go. light stripes on dark pants can also work in your favor. these claim to be

*also, yes, NO PLEATS on the pants

* a good pair of shoes is essential to having a good look... you don't need to spend a fortune, but you get what you pay for. not black reeboks/non-descript athletic shoes, something with laces or seams. maybe something like this? or this?

* seconding what everyone said as a hair cut plan---find a good salon and tell them what you need; they'll give you a style that will complement your face/head. just be prepared to spend more than $10.

* also, after looking at your picture, i'd say the heavier framed glasses someone else suggested would be great on you. maybe even some funkier ones. try a bunch!
posted by hulahulagirl at 6:51 PM on April 14, 2008

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