I want to be more stylish. Help? Looking for both general style tips and specific clothing recommendation.
February 24, 2011 5:01 AM   Subscribe

I want to be more stylish. Help? Looking for both general style tips and specific clothing recommendation.

I wouldn't say I dress horribly, just uninterestingly. For my job, I wear jeans (not too old, but not that stylish), perhaps a random plaid shirt from JCrew, maybe a brooks brother's shirt with a plain colored sweater, whatever. I don't have that much clothing. I do not wear cargo shorts, that sort of thing...I'm unstylish, not hopeless! Shoes are typically a pair of boat shoes I got on the cheap in south america (just so people don't think I am a bro ;), maybe some chucks, that sort of thing.

I am a stocky 5'6" white dude. My goal is to not come across as a boring, shabby dresser. First impressions matter, caring about how you look reflects a lot, etc. Historically I always had to dress quite formally in jobs, and would come home to jeans and a nice t-shirt...which is nice, but I want to have a better spectrum of clothing.

What I am looking for: good looking, but not OVERLY formal, clothes (I have plenty of slacks and plain dress shirts from Brooks Brother's). The sort of shirts, jeans, pants, etc that are sporty, but classic. The sort of clothes you could go to a decent restaurant in, or a nice place to drink wine or whatever. I dunno. I also don't want to look like another boring DC denizen and generally love color, but that's hard to incorporate...

So I am looking for general recommendations on HOW to sort of develop a sense of style, but also links to particular articles of clothing that you think are good looking or might recommend (even if it contradicts what I posted, I have admitted I don't know what is going on, CORRECT ME!). I especially need a new coat (I don't want to be another dude in a cliched pea coat...), and I'd like some new shoes (maybe a pair of not to formal dress shoes and a pair of boots, not sure). And less plaid from JCrew.

As far as budget, I certainly wouldn't say that money is no object, but I have enough to invest in a nicer wardrobe.

tldr: recommend me good looking clothing, especially a coat (heavy and light). Help me be stylish. I am a short stocky white dude.
posted by wooh to Clothing, Beauty, & Fashion (40 answers total) 38 users marked this as a favorite
Fit. Learn about fit, invest in a tailor, memorize your measurements. A fitted dress shirt will look much more flattering then a big blousey one.

For standard, bone average, easily available, reasonably well constructed support items ( the stuff that isn't ment to impress, undershirts, etc) I like L L Bean.
posted by The Whelk at 5:35 AM on February 24, 2011 [1 favorite]

Well, JCrew makes more than plaid. Get yourself some solid oxfords and a pair or two of their worn in khakis.
I would also recommend Target for clothes that look not so bad for how much they want for them. Stock up on plain-front pants (pleated make you look fatter, not thinner), some oxfords, some pull-overs (for when it's warmer).
Consider spending a little money on some good jeans (I'm partial to Levi's 501s, but that's just me). Quality jeans will cost a little more, but they'll last you for a good 10 years.
As for shoes, go to zappos. Browse around. In my neck of the woods, the sporting goods store is also a good place to find classic sneakers, but that may not be the case where you are. For leather shoes, don't rule out getting more boat shoes - they're back in. Everyone is also mad about "chukka" boots right now, which are basically the low-rise boots you could get from hush puppy and Thom McCan back in the day. Don't buy cheap here. As with the jeans, a good pair of shoes looks a whole lot smarter, and lasts a whole lot longer.
(on preview) yes, fit is going to be a big issue. Consider doing some online shopping to get some of the more rare sizes. You should also consider getting items altered. It costs very little money, and makes worlds of difference.
posted by Gilbert at 5:46 AM on February 24, 2011

Try on everything you buy (bar underwear). Find sizes that fit you and flatter you. Be ruthless - if something doesn't fit you properly, then don't buy it. This is probably the single biggest thing you can do to make yourself look better in clothes. I'm fairly slim, so I err on the side of slimmer. Not sure what a stockier guy should do, but I'd probably expect the same.

Colourwise - I'd mostly stick to simple muted colours. Experiment as much as you want, but solid colours are less complicated, and the nicely fitting clothes that you've got will flatter you rather than draw attention to themselves.

If you think a guy's well dressed, try and work out what he's doing that agrees with you.

I'm no fashionista, but those are the things I do to feel comfortable in what I wear.
posted by Magnakai at 6:07 AM on February 24, 2011

You don't say where you live, and I think that may matter.

Look at the videos on the What Not to Wear site for ideas

Russell Smith put out a book a couple years ago and has a column in the Globe and Mail that might help. However, he may be a bit urban and/or pinch for you.

Look closely at the men whose style you appreciate and try to pick out why. Flip through men's fashion magazines.

Flat fronted pants, sport coats
Find a tailor to shape jackets & pants to fit you properly.

Browse through some higher end deprtment stores like Nordstrom's or Holt Renfrew to see what they have on display that you think might work for you.

Find an independent men's clothing store that has stuff you think looks good and develop a relationship with the sales staff. Good staff will take care of you, remember what you own and steer you toasted choices that will look good on you. My region has these in more established, wealthier parts of town AND in traditionally Italian and Greek neighborhoods. Look especially in places where the population shares your shape to minimize disappointment.

If you like colour, buy some dress shirts in bright colours you like, possibly with contrasting collars & cuffs. Men may wear more than blue/grey/white and plaid!!!

Buy and wear nice belts. If it's cracked or visibly worn, throw it away. Real leather belts can be bought at TJ Maxx cheaply.

Buy clothes that make you feel good and you will enjoy wearing them.
posted by Heart_on_Sleeve at 6:10 AM on February 24, 2011

Not sure what a stockier guy should do, but I'd probably expect the same.

Speaking from experience, the thing that works for me is buying a bit looser and bigger and then having it tailored down to my specifics. For stocky guys, not being wedged into too-tight clothes will make you look much more finished and slick. (And avoiding the opposite problem, swimming in fabric, which is again, the importance of fit) Yeah try on everything. Twice. Suit jackets should close without effort, with no visible straining or warping of the fabric (you want a flat front) and pants should have clean lines straight down, not bunching around the ankles.
posted by The Whelk at 6:12 AM on February 24, 2011

Good advice above. Coats are tough, especially this time of year! Don't go too long, or it will make you look stockier. Military-inspired is big right now.

YMMV, but I'm a fan of mix-and-match. Wear the Brooks Brothers shirt with some broken-in jeans. Pair something vintage with something new. Mr. Arkham is about your height and build and he does have trouble shopping...it's not always going to be easy. (ProTip: Levi's online has a lot more sizes, including short rises with larger waists, than you'll ever find in any store.) You're going to have to learn to enjoy it, get things tailored, and always have your eye out for new pieces. Take a friend, the more brutally honest the better.

Not everyone in DC is boring, but it does take a bit of courage to stand out. Good luck!
posted by JoanArkham at 6:12 AM on February 24, 2011 [1 favorite]

Also, I vagually know Steve who writes this (British) fashion blog, and it may provide some inspiration.

There was also an excellent video series about dressing well and good style, but the name escapes me now, and I easy can't find it online. Maybe someone else will point you to it.
posted by Magnakai at 6:13 AM on February 24, 2011

Definitely get a tailor. Especially if you're not a "normal" body type, tailoring off-the-rack clothing will make all the difference and (depending on what you need done) can be relatively inexpensive.

Two sites I like - Put This On for general style advice and Nerd Boyfriend for more general "looks".

Having a set of basic articles in solid colors that can mix and match seems to be the best way to go, at least for me. Decide what you like, too - if you like the plaid button-down look, then build off that. Maybe get a different style of pant to go with it, a contrasting tie, nice wool blazer...

I would also take a little time to learn about how clothes are constructed and how to determine what's good quality. Maybe I'm projecting biases on my clothing, but I feel better dressed in clothes that are made well.
posted by backseatpilot at 6:13 AM on February 24, 2011

The Sartorialist
posted by j03 at 6:16 AM on February 24, 2011 [3 favorites]

And personal persnickety detail - unless there is a very good reason for it (I:e Hiking), I always choose all natural fabrics - cotton, wool, linen, etc. Cheap plastic shirts feel like I'm wearing suran wrap (touch your clothing, what goes against your skin should feel nice) and they wrinkle *instantly* and the light doesn't hit them right and argh. It makes despair.
posted by The Whelk at 6:18 AM on February 24, 2011

Read some style blogs! I am a huge fan of Put This On, although the content that's on the front page isn't too exciting. I also like An Affordable Wardrobe. Those blogs have fairly good blog rolls, although a lot of the prep/trad blogs can be pretty snobby and a few of them are racist. For something completely different, I like The Dandy Project, especially when the blogger does DIY style projects--even though mostly his style isn't something I wear at all.

On colors--many people have a stronger sense of color than of fit or style; you can probably trust your color judgment. Same for patterns.

Shoes--shoes elevate an outfit. Nice shoes last longer and look nicer and are a lot harder to thrift. If you're putting money into anything, put it into shoes. A good leather shoe has as many of these characteristics as possible: a sewn-on sole, not a glued sole, since this means that it can be resoled if needed; a complete leather lining to the toe, since this is more durable, comfortable and breathable than fabric; an outline that follows the shape of the foot rather than being "puffy" like an athletic shoe. If you can find shoes that don't have corrected-grain (basically plasticy-dye-coated) leather, that's even better. Square toes are widely deprecated.

Some nice shoes include Clark's desert boots (nice primarily because very, very simple and sturdy); Allen Edmonds dress shoes, made in the US; and the newly relaunched Walk-Over suede bucks and derbies, also made in the US. For Allen Edmonds and Clark's, you can go to a store and try on a variety of styles, then keep your eyes open for your size at a discount on Ebay or elsewhere online. If you want even fancier shoes, the various style blogs will soon instruct you about Aldens, Crockett & Jones, and how to spend $1000 per pair...I myself wear English boots from Tricker's, bought in various hole-and-corner, discounted ways.

For casual boots, check out Baker Shoe. They stock Red Wings, which are nice, and White's, which are nicer. A fellow simply couldn't go wrong with a pair of White's semi-dress or Americana boots. Again, these are made in the US and will last a good long time. When you can, alternate your shoes so that you're not wearing the same pair every day. This allows them to dry out and allows the footbed to decompress between wearings, lengthening the life of the shoe.

If you're looking for color, what about checking out some Italian makers, Zegna, etc? They seem to go in for brights a bit more. If you do an Ebay search on Zegna, Ebay will pop up suggestions for similar searches, which is very helpful for getting to know possible brands.

And what about getting some corduroys? They usually come in a wider range of colors--you can get wide-wale ones for work and narrow-wale ones for casual. You could easily wear, for example, some rich-blue wide-wale corduroys in a trouser cut with a shirt in an interesting color or pattern and a nice sweater.

Have you considered the full range of men's shirtings? All those style blogs have recommendations for tailors, both mail-order and local (many of which the bloggers try and then review). There are so many different types of collars and different shirting fabrics--you could get some unusual and striking shirts. And honestly, just looking at all the possibilities will help you spot new shirts at the thrift store or out shopping elsewhere.
posted by Frowner at 6:33 AM on February 24, 2011 [1 favorite]

Go to Amazon or eBay and pick up a copy of Color for Men by Carole Jackson. Really. It is an older book, but the theory and advice is timeless. I like it better than the female editions. Jackson is the original and best on this topic; accept no substitutes.

It will help you a lot with color. Someone above said to use muted colors, but if your hair, skin, and eye color contraindicate muted colors, you will look worse. Trust me.

Figure out what color palette is good for you, buy a week's or weekend's worth of the brightest colors in shirts from L.L. Bean (polos or tees). Wear them, and rake in the compliments. You will thank me.
posted by jgirl at 6:39 AM on February 24, 2011

My husband is addicted to Style Forum. It's useful for inspiration and for learning more about what cuts & combos are flattering.
posted by feidr2 at 6:56 AM on February 24, 2011

Some great stuff, and I look forward to hearing more. Let your own style shine through as well, that's how I learn.

Quick notes: I am in DC (I sort of implied it, but I'll make it explicit). I do not like polos or khakis. I might be swayed on polos, probably won't be on khakis. My aversion to polos is this: I have tattoos on my upper arms that are visible in t-shirts. Once I show the tattoos, I feel it sort of contradicts the preppiness of the polo. When I am looking to dress nicely I usually assume that I will cover the tattoos...short sleeves usually mean I roll up my sleeves (tastefully). Look forward to hearing your thoughts on this as well.
posted by wooh at 6:56 AM on February 24, 2011

I've gotten some good mileage out of mixing prep and non-prep elements ( Navy blazer, red red and white silk tie, silver skull lapel pin, gray slacks, red sneakers, friend calls it "Addams Family Goes To Princeton") which could work for you in less formal, more relaxed environments.
posted by The Whelk at 7:01 AM on February 24, 2011

On mature consideration, you sound to me like a fellow who could use a tailor, especially with the "don't like khakis" thing. (I assume that you do like some variety of chinos in alternate colors? Otherwise you're pretty much down to jeans and flannels/tropical wool.)

It's not actually too expensive to have a pair of pants copied, although to keep things cheap they usually need to cut the pants up to make the pattern. You could get pants copied in some colored twills, for example--a deep blue, a deep red, etc. Or some more unusual suiting fabrics. And what about Nantucket Reds?
posted by Frowner at 7:09 AM on February 24, 2011

I am intimidated by the idea of a tailor and not sure how to effectively use one. Buy clothing and get it all altered?

As far as khakis, polo+khaki just strikes me as the "I am a sysadmin" look. Chinos seem fine in theory, for the right pair. In general I've always just worn either dress pants of jeans, but definitely need to expand.
posted by wooh at 7:22 AM on February 24, 2011

wooh: "I do not like polos or khakis. I might be swayed on polos, probably won't be on khakis. "

Don't let anyone sway you on polos. If you're trying to look classy and unique, definitely the wrong way to go.

On khakis: wear a different colored chino. Tans are nice, browns are nice, grays are especailly nice. Whatever catches your eye. On a coat: I have a single-breasted, car coat length wool coat from London Fog that I find to be 2.5 seasonal, roughly. Some DC specific recommendations: Unique Thrift in Maryland has some surprising good finds. Dr. J's Vintage on U Street has some great stuff for inspiration.

In general, your personality should dictate your style and not the other way around. There's not necessarily wrong choices here, there's just taking the things that you like and stepping them up a bit. If you like plaid shirts, for example, look into some new or vintage Woolrich or Pendleton shirts: they're classic, often feature brilliant colors, and show that you pay a little extra attention to how you look. Being a little stocky makes things a little harder, admittedly, and the advice upthread about slimming cuts are well advised. However, in general

1) Buy thoughtful or nice versions of the colors, patterns and textures you like or represent you well
2) Be respectful of the general level of formality of any event (don't wear a tie if it isn't called for, do wear one when it is), but wear good quality garments nonetheless. There are good jeans and crappy jeans just like there are good tuxedos and crappy tuxedos.
3) Do more with less - one nice item is always better than two crappy items
4) Make sure that every item you wear has a clearly delineated function and isn't just an affectation. When can you wear a hat? When it's cold and you want to cover your ears, when it's raining and you want to keep your head dry, when it's sunny and you want to shield your eyes. You get the idea.
posted by l33tpolicywonk at 7:27 AM on February 24, 2011

wooh: "I am intimidated by the idea of a tailor and not sure how to effectively use one. Buy clothing and get it all altered?"

There's a lot of strong opinions about this, but I've found tailoring to be generally unnecessary. YMMV, by a lot, but I'd only use a tailor when you really feel like a small tweak would make a big difference (for example, the sleeve length of a suitcoat). In general, stuff should fit in the store.
posted by l33tpolicywonk at 7:28 AM on February 24, 2011

I think if your tattoos are classic (ie. not Biro-style scrawled names or poorly rendered faces) then you can use them as part of your outfit and not an obstacle to it. I'm not totally clear on what 'preppy' exactly means as I am British (though loads of public school kids are tattooed) but if you like your tattoos you could go for a kind of teddy boy/rockabilly inspired look, which can be as 'smart' as you like but not anodyne.
posted by mippy at 7:33 AM on February 24, 2011

Your tailor will tell you all that...I'd suggest asking metafilter or googling around online for a good tailor in DC (I'm sure there's lots and lots). For alterations, you won't need a fancy one, just a reliable one. You'll bring in your clothing and he or she will measure you and discuss how you want your clothes to fit--do you want the waist snug or with a bit more ease, etc? Bring one piece of clothing first to see if they do a good job.

To have clothes copied, you'll need a slightly better tailor. An even better tailor will make you clothes from scratch. If you have a favorite pair of pants or you want them in a different color, you can get them copied; a good tailor can do this without cutting up the original pair to make the pattern, but if you have a throw-away pair to copy, you can let them cut those up.

A relationship with a tailor is widely held to be helpful. I don't have a good tailor, and it makes me sad. (Perhaps I should level with you here; I'm female, but for reasons of build (no hips!) and gender presentation, I wear mostly either actual men's clothes (shoes, sweaters, accessories) or mannish clothes (most other things).) So I have some interest in this. I have gotten men's coats tailored down to fit me.

I personally don't like polos too much, although a polo sweater over a button-down looks nice.

Some basic suggestions - 1. avoid synthetics except for serious outdoor/wet-weather clothing; balance a bright color with a traditional cut or an innovative cut with a traditional color; 2. get good accessories - nothing says sysadmin like a black nylon shoulder strap laptop bag (although honestly, I find sysadmin types pretty cute a lot of the time); 3. keep an ongoing list (I have a chronic google doc about what I'm looking for, what I got, what works, what failed; it's been super-helpful); 4. buy the best you can afford that is suitable to your lifestyle, so if you're constantly getting caught in the rain, don't buy a nice leather bag, if you walk a lot, get rubber/vibram soled (sewn on!) shoes, etc. Don't be hornswoggled by style blogs telling you to buy fancy English gloves if you're always leaving yours on the bus.
posted by Frowner at 7:44 AM on February 24, 2011

l33tpolicywonk: I think I agree generally with you...I will admit that I have a sizeable rump (not from weight, really, but from my latin mother) and I guess in some cases it might help me find pants that fit me better or something.

mippy: I can agree that my tats could be incorporated into my fashion, but for the time being I don't know if I am cool enough to pull that off yet ;)
posted by wooh at 7:48 AM on February 24, 2011

I am intimidated by the idea of a tailor and not sure how to effectively use one. Buy clothing and get it all altered?

As an argument for finding a tailor, consider most clothes sold for men at low- and mid-range stores in America tend to be very boxy and unflattering, especially if you differ from the standard body types they design clothing for.

I'm fairly short and narrow-torsoed but with big thighs, so if I find pants that fit in the waist they're generally too long and too tight in the leg and shirts that fit in the collar balloon around the chest. It's relatively easy and inexpensive to get pants shortened and shirts taken in.

I like to go to thrift/consignment/"vintage" stores to find really high quality used clothing - especially suits and jackets, which I like wearing but aren't part of the work dress code. I can find something that mostly fits, take it to the tailor, and he can figure out how to get it perfect. Even if it doubles the cost of the suit, I spent so little on it to begin with that it's usually a bargain compared to buying new.
posted by backseatpilot at 8:12 AM on February 24, 2011

Another vote for The Sartorialist! Check out the pix of people with your general body type to get some new ideas. (I find this works better than staring fixedly at interestingly-garbed strangers on the street but ymmv.)
posted by elizardbits at 8:22 AM on February 24, 2011

Come up to NYC for some free appointments with the personal shopping services at stores like Saks and Bloomingdale's that sell lots of styles/brands from uber conservative to crazy stylish and in a range of prices. I've done it once and these people are worth their weight in gold. Plus, there's no obligation to buy.

Essentially, they can tell you 1) what kinds of clothing make sense for your build and 2) which designers make clothes for your body type. You'll learn things like: so-and-so brand cuts for tall skinny guys, so no need to ever look at that stuff, whereas the next designer has guys with your build as his primary customer.

I really suggest NYC because the shopping options in DC are so lame in comparison and because of your self-described Latin rump and tats. Hiding and accentuating one or the other is arguably an NYC specialty.
posted by paindemie at 8:31 AM on February 24, 2011

There's so much to learn. To hit the ground running, you can start by dressing all in black, as fitted as you can be comfortable in. Just please make sure you keep the shoulder area meticulously clear of any dandruff by checking it multiple times a day, as applicable.
posted by Dragonness at 8:54 AM on February 24, 2011

There's so much to learn. To hit the ground running, you can start by dressing all in black, as fitted as you can be comfortable in. Just please make sure you keep the shoulder area meticulously clear of any dandruff by checking it multiple times a day, as applicable.

Hm. When I see a guy dressed all in black, I assume that he is an internet person, a ren fest person, a goth or a working class city kid wearing sports gear. Or maybe one of those guys who operate the life-sized Japanese puppets! Wearing all black gives the strong impression that you think black is intense and mysterious and that you wish to appear intense and mysterious. There's a guy who takes my bus who dresses all in black, but sort of fifties formal--black fedora, tailored black overcoat, black leather briefcase, black scarf, black button-down, etc. He actually looks pretty sharp, but he is also pretty obviously an internet person and little bit aspie-ish. He's also tall and thin. I do not support all-black ensembles for the short and pudgy, and I say this as a short, definitely stocky (though hipless!) person.

If you want to wear dark colors, I feel like charcoals, navies and blacks together are the way to go.
posted by Frowner at 9:21 AM on February 24, 2011

(And of course, if you are an internet person, a goth, etc...it makes complete sense to dress as an internet person, a goth and so on. It's just that you'd mentioned not wanting to look like a sysadmin.)
posted by Frowner at 9:49 AM on February 24, 2011

Frowner, the fit is where the difference between stylish and frumpy comes in.
posted by Dragonness at 10:19 AM on February 24, 2011

Are there good tailors in DC? I'm not so sure about that.
posted by The Lamplighter at 10:56 AM on February 24, 2011

Are there good tailors in DC?

Yes. It just appears that none of the white people who work on the Hill patronize them. If you go out dancing at a Dominican nightclub, frex, you will see some tailoring.

Stick to your guns about the polos, wooh! Investing in some attractive, well-made shirts and having them tailored (or getting them custom-made at a place like Thomas Pink will be an initial cash outlay that will pay off over the long run--good shirts last more than twice as long as cheap shirts.

Also, check out Barney's for more cutting-edge style options than you can find elsewhere in DC.
posted by Sidhedevil at 11:29 AM on February 24, 2011

I would look first at shoes. Good shoes. Good shoes are expensive, and a single pair may cost as much as half your initial clothing budget for a small, but versatile, wardrobe. Allen Edmonds are good, but if you can get shoes from reputable English makers, do so. (Tricker's, etc.) In addition to lasting a long time (if you take care of them), you can find models that have versatility.

As a foundation, consider a couple of books to get started: Gentleman: A Timeless Guide To Fashion, and Alan Flusser's Dressing the Man: Mastering the Art of Permanent Fashion. Both have useful tips on deriving a style, and loads of information on how to wear clothes properly. Flusser's book is probably more helpful in terms of finding colors to work for you, though in this department, its a starting point.

You can and should look at various style blogs, etc., but I've found that they're more helpful once you have some kind of foundational understanding of both why clothes are appealing (both to you and to others) and what your own personal style is or will be.
posted by Hylas at 11:40 AM on February 24, 2011

Frowner: I'm pretty sure Dragonness was joking, as per the "brush your shoulder many times a day" comment.

Paindemie: I love that suggestion! I am pretty shy about the idea but I think it is actually a pretty excellent one. I just have to go in ready to drop a little cash!

I think that fashion blogs are great to look at, but I am bad at sort of...internalizing it into my own sense of fashion. Perhaps with a little more experience or something, but the problem with me and clothes is that the options just feel so overwhelming.

And it's settled, no polos will touch these guns.

Thanks so much for all the great advice. I promise I am mulling over it all. Great stuff. If anyone has anything else they think would be useful or just want to support or talk about what others have said, it's all welcome! Thanks so much!
posted by wooh at 1:14 PM on February 24, 2011

I got a great recommendation for a DC tailor here. When I was there last, there was a guy with his favorite pants that were no longer available, to have them make copies.
posted by JoanArkham at 1:37 PM on February 24, 2011

1. Make sure everything fits well. Nothing should sit oddly on your body or be intensely uncomfortable.

2. When things get holes or visable wear, or even if they just become out of shape from washing and wearing, get rid of them.

3. Learn what colors look good on your complexion.

You don't have to worry about things being totally complex, super unique, fussy or really "special" in any way. Just make sure your clothing has some thought put into it, that you look tidy and clean, and that things fit your body well and you're comfortable in them (but not sweatpants on saturday morning comfortable. I mean, not actively uncomfortable.)and that everything is in good repair. That will go a long way to helping you look more tidy in general. And you can always add in a special, favorite, very "you" wardrobe peice when you find a thing that just, fits your style perfectly.

And a note to the darker-ly inclined men out there-

I don't mind all black on guys. Just, NEVER EVER black t-shirts with slogans on them with black cargo pants. NEVER. Black trousers and a plain black T? fine. Black jeans and plain black tee? also fine. A little rockabilly but fine.

And trenchcoats should always be inspired by burburry and the 1950's. Tidy, no stupid stuff on them. No "van helsing" leather trenches, PLEASE. Leather is for moto or bomber jackets on men. But a crisp, tidy, 50's film noir-ish black trench? yes please. for all those men that want to look dark and mysterious, take your ideas from the 50's and go a bit minimal. Film noirs and James Dean and Marlin Brandow. NOT 1990's Kevin Smith.
posted by RampantFerret at 1:54 PM on February 24, 2011

Oh yeah, also avoid synthetics like plague unless it's sports gear. (go cotton, rayon, linen or wool. Never 100% polyesther, especially for suits and sports coats. )
posted by RampantFerret at 1:57 PM on February 24, 2011

You need the current issue of Esquire, which has a whole extended style section, and lots of good ideas. My two basic tips (as a woman, FYI): ditch the sports logos, and get cool shoes. They really do matter.
posted by FlyByDay at 2:09 PM on February 24, 2011

Since you like the free personal shopping idea, a few more thoughts:

Schedule the appointments early in a season, e.g. now, as opposed to when everything is on sale, so you can take notes and maybe just buy one or two things. When the sales begin, you'll know exactly what you're looking for and can probably get some of it online and at similar stores in the DC area.

To my surprise, it turns out that the personal shoppers don't expect you to be buying the crazy fancy stuff. I work in the nonprofit sector and that was all the shopper needed to hear to steer me to the floor with clothes I might be able to afford. I was never pressured into looking at items I couldn't possibly pay for. She even made a point of suggesting things that were on sale and those are what I ended up buying.

On the shyness: I totally understand. But no one will know the questions you asked, the things you tried on. You'll just show up in DC looking really great, and knowing a lot more about what to search for locally.
posted by paindemie at 3:25 PM on February 24, 2011

Nordstrom should have both a good tailor and a personal shopper.

Then there's always Georges de Paris, 650 14th Street Northwest
Washington D.C., DC 20005-2004
(202) 737-2134.
posted by jgirl at 4:21 PM on February 24, 2011

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