Clothes make the man. Naked people have little or no influence on society. Mark Twain
April 16, 2011 11:04 PM   Subscribe

I need a major rehabilitation of my wardrobe. I kinda know where to start, but I need any fashion help possible. Caveats: I'm a guy, I'm overweight, I have a limited budget for now, and I'm style-impaired.

This week I realized that my last comfortable pair of jeans were now Sunday jeans (they are holy) and I need to buy some clothes. I started trying on some of my clothes and found a whole hell of a lot of them don't fit as they are too small or just fit wrong, being tight in some areas and huge in others. I also realized that I don't even have a suit I can wear. I went down to a couple of stores today and couldn't find any jeans, khakis or dress pants that fit correctly, usually too tight in the legs and 3-4 sizes too big in the waist.

I work in a fairly casual office. Minimum dress is jeans and a polo or long sleeve t-shirt, up to wearing a suit. Outside of work, I'm usually stereotypically jeans and a t-shirt. I lack any sort of nice jacket to wear. I do have some button-down shirts, a couple of meh pairs of khakis. I have dress shoes, but they are on their last legs as well. I am in the opinion that I'd rather pay more up front for things that will last forever than less now for crappy stuff that won't stand the test of time.

My questions come down to this: How do I get my wardrobe back in line? My budget for the time being is probably around $1000 total. In a few months, I can probably put another $1000 towards my wardrobe. I'd like to get at least one nice suit, a jacket I can wear in all sorts of circumstances, a good pair of shoes, at least 4 pairs of jeans, dress shirts, casual shirts, all things that make me feel more like an adult and not a college student anymore. I would say that a suit, jeans and a coat/jacket are priority. Second in line would be an awesome pair of shoes, dress shirts, and button-down shirts. I have plenty of very casual clothes, such as t-shirts, crappy jeans, etc that's great for being at home. Would I benefit in finding a tailor? How should clothes fit before taking them to a tailor? Who's good here? Is custom clothing needed and/or in my price range? What stores in the area or online are winners for someone of my dimensions? What styles should I go with?

Relevant details: I am in Portland, 27, male, 6'0" and around 300lbs. My typical size clothes are somewhere between 2XL - 3XLT, pants are somewhere between 42-48 waist, 30-32 inseam, no real clue on shirt/jacket sizes, shoes around 12. Some clothes I can manage to get in regular stores, sometimes I have to kick it up to the big and tall stores. Finding a friend who is fashionable and good at this might be a stretch for me as I don't know anyone that I'd describe as "fashionable."

Hope me MeFis!!!
posted by Mister Fabulous to Clothing, Beauty, & Fashion (19 answers total) 7 users marked this as a favorite
Eddie Bauer might be a good choice. Their stuff all kind of goes together so it's easy to put together several outfits because everything more or less "goes." They're pretty good with sizes, too, though you might need to order online for some bigger stuff. Sorry can't help with more specifics; good luck! I'm going through the girlie version of this crisis right now and will be watching this thread with interest.
posted by Neofelis at 11:54 PM on April 16, 2011

By "a jacket I can wear in all sorts of circumstances" do you mean an outerwear jacket (like a raincoat or pea coat or leather jacket)? Or do you mean a blazer/sport jacket?
posted by LobsterMitten at 12:03 AM on April 17, 2011

Response by poster: By "a jacket I can wear in all sorts of circumstances" do you mean an outerwear jacket (like a raincoat or pea coat or leather jacket)? Or do you mean a blazer/sport jacket?

Hell, I probably should get both. I've been thinking a pea coat, military jacket or car coat, whichever would look better on me, first. Blazer/sport jacket later.
posted by Mister Fabulous at 12:08 AM on April 17, 2011

So am I right that your shopping list is roughly this?

-dark gray suit (dark gray or "charcoal" is the most versatile color if you're only going to have one suit and want to cover all occasions)
-outerwear jacket (pea coat, car coat, etc)
-[maybe some nice-casual pants that are not jeans? ]

-good pair of black dress shoes (formal, not everyday)
-dress shirts
-button-down shirts
-casual shirts

The first thing to think about is how expensive a suit you want. The cheapest ones I'm seeing at Men's Wearhouse are in the neighborhood of $200. Probably nicer ones will be more like $400-500. Is the latter something you're on board with? Would you be up for paying even more to get a super great suit or are you looking for "good suit" rather than "great suit"?

Second, is your goal to have a style that's fairly classic/traditional, or do you want funkier/trendier/more individualistic things? (This may be a function of what styles are like in Portland or in your social circles)

(I have to get offline now, but there have been many useful past questions about how to transition from "college" dress to "working, late-twenties" dress, including ones with your body type -- if you're up and noodling about this tonight, you might try clicking through the men and mens clothing tags to see if you can find them.)
posted by LobsterMitten at 12:22 AM on April 17, 2011

Best answer: I'm also a hard to fit guy (6' 5", 280) about your age and I've found Lands End to be really good. I like their tailored fit shirts / pants but for you the regular fit would probably be perfect.

A couple of general tips for big dudes like us:
-- avoid pleated pants -- flat front is where its at for the big-thighed.
-- wear your pants at your natural waist, even if this means above the gut/muffin top.
-- vests can be a good look -- either sweater vests or waistcoats. Make sure that they fit!
-- in general, make sure your shirts fit. If you're like most fat guys I know, shirts that fit you in the neck will still be way too big in the stomach (if not, awesome!). But don't be surprised if you have to take stuff in to the alterationist to get it brought in at the sides. Most dry cleaners can do this, and they charge less than $20 a shirt.

Some staples that you'll want to get:
-- oxford shirts (thick, cotton shirts with button-down collars) in white and blue. Pink and yellow if you want. I like these; they're cheap (and go on sale all the time), and they come in big sizes.
-- jeans that fit well. Levi 501s are great, and come in all sizes. Get a dark wash. Avoid bootcut pants!
-- some chinos in any color. Again, Lands End: these are solid pants. Go for the loud Andy Bernard colors if you want, or just some khaki and navy.
-- wool trousers. These can be part of a suit, but they say it's better to not wear your suit trousers on their own too much or they'll wear out quicker. I have a pair of these that I like; you can buy them on their own or you can also get the jacket to go with so you can wear them as a suit. Avoid black unless you're an FBI agent or go to lot of funerals - you want some shade of gray.
-- 2 pairs of shoes: some simple casual sneakers (neutral Vans Authentics are my favorites) and a pair of brown leather dress shoes (Allen Edmonds are solid shoes and they show up all the time on eBay for <>this LE vest (any color) [note - these are sized hella big; I normally wear a 17.5 neck / XL tall and I wear a large or even medium LE vest.)

"Nice Dinner with SO"
shirt: LE oxford
pants: LE trousers
sweater: this in a dark color (not the same as the pants!)
tie: any - go for something either solid. If your shirt is neutral (white or blue) you're safe with most colors on the tie.

"Drinks with Buds"
shirt: LE oxford (notice a pattern?)
pants: Levi 501s
optional: tie. This is a real Ted Mosbyish look but I like it a lot.
posted by rossination at 12:29 AM on April 17, 2011 [4 favorites]

I too have to get off the internet, but PM me if you want more ideas. I really like geeking out about menswear but I haven't always been this way --- and I understand how much it sucks to pretty much never be able to buy well-fitting, reasonably-priced clothes in stores.
posted by rossination at 12:32 AM on April 17, 2011

Salvation Army on SE Grand. (I think the entrance is on MLK). The Goodwill Superstore in SE.. not sure exactly where. Buffalo Exchange on SE Hawthorne. Also worth a shot - Red Light, across from BX.

I'm not advocating second hand clothing because its, like, cool you know?, I'm advocating it because with a little effort you can find great stuff for nothing. I've got some of my best clothes from that Salvation Army. I used to go there once a week, and even then I'd only score something good every few times. So then I'd go to Goodwill. And maybe BX. And in the course of an afternoon score a shirt or two.

Hitting the used clothing circuit I built up a nice wardrobe, fast, and for less than a hundred bucks.
posted by special agent conrad uno at 2:31 AM on April 17, 2011

I buy most of my clothes at the Salvation Army and other thrift stores, but I wouldn't recommend that route to someone who describes themselves as fashion impaired. To get great deals on clothes at thrift stores you have to devote time and energy to it, and also really enjoy it.

My husband is a lot like you, sizewise and not good with fashion. We get his clothes at Land's End and at a couple of smaller stores in town that usually have the kind of things he wears and we know the sizes of the brands are usually consistent so I can buy stuff for him without him being there. It's worth spending time to find a few good places where you know and like the type of clothes they have, that will save you a lot of time down the road.

If your weight is stable, it's good to buy the best quality clothes you can that will last a long time. If you find something you really like that fits well, buy another one in another color!
posted by Melsky at 4:07 AM on April 17, 2011

Best answer: This might only marginally help you, but Put This On is an amazing, practical guide to dressing like a grown up. You've no idea how much I want a women's version of this blog.
posted by nerdfish at 4:30 AM on April 17, 2011 [4 favorites]

Best answer: Would I benefit in finding a tailor? How should clothes fit before taking them to a tailor?

Tailoring can definitely expand your options, and shopping is a lot less frustrating if you don't need everything to fit perfectly right off the rack. Here in NYC, a lot of dry-cleaners do alterations, is it the same where you are? For men's business suits, the store might do alterations in-house, but for simple things like hemming pants or getting them taken in at the waist the dry-cleaner tailor would be fine.

As far as how clothes should fit before tailoring, the trick is to fit the widest part of your body first. So, for jeans, if you find a pair that fits you comfortably on the thighs/crotch but is way too loose around the waist, it's simple for the tailor to just cut that extra fabric out of the waist. I've never had to get a shirt/jacket altered, but I believe it's the same principle - if it fits the shoulders/neck, they can put in some dart seams to get rid of excess fabric in the torso.
posted by oh yeah! at 6:54 AM on April 17, 2011

As far as the shoes go, Oxford wingtips will never be out of style.
posted by thsmchnekllsfascists at 8:54 AM on April 17, 2011

Best answer: If you want an interesting suit—as opposed to something completely conventional from the Men's Wearhouse—see Seyta at Duchess Clothier, 11th and Division. Not your generic sarariman uniform. I think her "Scotch Basic" line started around $500 last I saw a price sheet, but they go up from there.

I've only had things dry-cleaned at his adjoining shop, but Abraham Lee on NE MLK is apparently an insanely great place for alterations as well as bespoke suit tailoring. Might stop in there if it's convenient to you. I'd certainly investigate them for altering your off-the-rack purchases.

For jeans or dungarees in sizes above a 42, personally I like the no-nonsense Duluth Trading (though I think you would do well to avoid anything with cargo pockets as a matter of style).
posted by mumkin at 9:27 AM on April 17, 2011

Best answer: Is custom clothing needed and/or in my price range?

Custom collared shirts are definitely worth it, and definitely in your price range as long as you buy online. I love Modern Tailor - they let you try a nice blue oxford for $30 with shipping the first time, and after that custom-made shirts end up being around $40-$60 each. Lots of threads about them on Styleforum if you need more info.
posted by ripley_ at 12:41 PM on April 17, 2011

Response by poster: Thank you all for the responses so far. I've ordered a pair of jeans and pants from Duluth Trading, as I fell for their ads as well as the reviews. Most people responded that their stuff pretty much lasts forever and looks good as well, not to mention their size range should work out.

I've seen a lot of the Duchess suits, and it looks like they advertise their specialty suits more than anything, but I've read reviews and write-ups that say they kick out some stunning traditional suits. I'm thinking I will be stopping in there as soon as I have a chance, even if it means shelling out $650+ on a suit, something tells me it will be worth it.

I have a couple of new questions since I've been reading the responses and through the threads: I'm tempted to get some high quality shoes in the next round, something of the $300 and lasts 20 years variety. Do I get brown or black first?

Second question: Where is a good place to find a good classy-looking coat, like a pea coat or car coat? The caveat again is size. I had one friend suggest H&M but I know that's a joke as they don't make for my size body.
posted by Mister Fabulous at 10:41 PM on April 17, 2011 and the blogs they link to are great for style tips.
posted by Grimp0teuthis at 12:00 AM on April 18, 2011

For coats, check Lands End or maybe Gap -- Banana Republic or J. Crew on sale could be good as well.
posted by rossination at 12:27 AM on April 18, 2011

The answer to your shoe color question depends, I think, on the color composition of your wardrobe, which'll depend on what looks good on you. I'm an earth-toned guy who wears almost exclusively browns and greens and burnt oranges and whatnot—you'll almost never see me in blue, black, or grey—so almost all of my shoes are brown. You, however, may be the kind of guy who was born to wear navy and charcoal, in which case I'd assume black first, because you've gotta hew to your hue.
posted by mumkin at 1:51 AM on April 18, 2011

You, however, may be the kind of guy who was born to wear navy and charcoal, in which case I'd assume black first, because you've gotta hew to your hue.

Except that those are both suit/pant colors for which brown is the appropriate shoe choice. Black shoes are for black suits, and black suits are for funerals and weddings. There's such a limited use for black in a standard wardrobe that you should definitely invest in brown shoes first. A pair of Allen Edmonds Park Avenues will last decades with proper care, and while they won't turn any heads, that's not what you want in dress shoes anyway. And then you can start salivating over a pair of Alden longwings in cigar shell, which will absolutely turn heads because they are the most beautiful pair of shoes.
posted by brozek at 3:41 AM on April 18, 2011

Best answer: A lot of people have provided you with good ideas about basic items and basic colors, but I want to talk a little about fit and style.

Fit is important, regardless of size. It's the difference between looking well-dressed, and looking like you rolled off the couch.

For shirts or sweaters, fit is, above all, determined by the seam that goes from the neckline across each shoulder. And that seam (it looks like a line) should end at the exact point your shoulder meets your arm, on both sides.

But fit in a top is also determined by how well the sweater or shirt drapes across the rest of your body. A lot of mass manufactured merchandise, and particularly men's wear, is cut too large these days. What this means is a lot of this stuff pretends no one has a stomach. People get fooled into liking this because they think that a "boxy" fit hides any figure flaws around the waist. But that's not true. Instead, this kind of cut just makes you look like a box, and if you're big already--or especially big on top, rather than low-waist on down--it'll make you look like a box on stilts or sticks. Not a good look.

The ideal female body is illustrated in the classic hourglass silhouette, where the shoulders and hips are a little wider, and the waist indents.

There's a classic men's silhouette too. If you remember seeing silhouettes in children's books of early settlers cutting wheat with a sickle, you may recall (apart from the man's sunhat) that the farmer's shoulders were really wide and the waist--as with women--was indented. Another way to think of this is to imagine an upside down triangle with one point aimed right at the navel and the other two pointing at the edges of each shoulder, and then long slim legs.

What this means for clothes is you may end up buying several shirts where you need a tailor to gently taper the seam from under the arm to the waist, so it gets closer to the body (but never tight) the closer to the navel it goes.

This is especially important when it comes to suit jackets which tend to be made of heavy fabric and have padded shoulders. The side seams of men's jackets should also be a little tapered to the waist, and the slit in back should be (contrary to what you might think) closed, not open. That gives the jacket more structure at the bottom, which further helps show off the waist a little.

As a tall man, you should also play up your height. That means strong vertical lines, and as few horizontals as possible. So a vertically striped shirt is good, but a horizontally striped one is bad. A zippered (!) sweater will be a little stylish and will make you look taller and slimmer than just a pull-over. On suit coat-type jackets, you want to look for a long V (the area from the bottom of your neck to the top button on the jacket), which will also enhance the vertical effect. Also, on jackets, pay attention to where the side pockets point. Ideally, they should be a little angled, again pointing down toward the navel, rather than purely horizontal.

Finally, and again on the subject of style, you might consider a leather jacket like the one Marlon Brando used to wear. The strong zipper, wide V neck, angled pocket, and mini-front belt (look at how this jacket tapers!) will all make you look slim, tall, and cool.


Where you where your pants on your waist will depend on how your weight is distributed. If you carry more weight in your stomach than your hips, the difference in circumference may be the difference of a size or two. That means that pants that fit your high waist (around the navel) will swim on your butt or hips. If that's the case, buy lower waisted pants. If it's not than buy them at whatever waist height you like. Whatever kind you buy, make sure to look at yourself in the mirror to check there's no bagging at the seat. Make sure they that are flat fronted (around the pocket area) and don't have lots of little seams (which can read as puffy). Also, don't buy any pants with cuffs—again it's too horizontal.

I just know you're going to look smashing!
posted by Violet Blue at 1:54 AM on April 19, 2011 [1 favorite]

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