Fashion advice for a 22 year old

I’ve come to the realization that my entire wardrobe basically consists of jeans, hoodies, t-shirts, and shorts. I have a few button up shirts and dark pants for job interviews and special events, but I have nothing that’s really “dress casual.” I’m heading off to grad school next year and I would like something to wear to give a good first impression. I’m not going to go out a buy a suit and I’m not walking the red carpet. I’m looking for something to wear to gallery openings and dinner parties and even the occasional date.

Oh, and I’m overweight and I look like a younger, slightly less hairy Zach Galifianakis, so it’s an uphill battle from there. The internet is only good for vague conflicting advice (Wear stripes! Don’t wear stripes! Polka dots!) so I throw myself at the mercy of the Dope.

As I see it, men’s wardrobes, broadly speaking, have five fairly well-defined levels of formality. From most formal to least:

  1. Tuxedo/morning jacket/other formalware
  2. Suit and tie
  3. Dark Pants, button down shirt (tie optional) (this is what I’d call ‘dress casual’ for men, but you seem to define it differently)
  4. Khakis and polos (‘business casual’)
  5. Jeans, t-shirts, sweatshirts

I’d think that dinner parties and gallery openings would call for level three, sans tie, which you’ve already got. Most of the guys I dated went with option four on dates. Get some khakis, I guess.

As to what’s most flattering for your body type, that gets beyond my abilities. Other, wiser folk should be along shortly.

I would suggest investing in one or two good um…sports jackets, maybe they’re called? Less formal than a suit, but turns the ‘dark pants-polo’ into something that would slide into just about any occasion not actually requiring a tie.

My sweetie is a big guy, and the Big and Tall Men’s stores really have some nice options.

(Male, 40)

Find a female friend with a good sense of fashion and get her to spend a day with you going to some department stores and men’s clothing shops to try stuff on. She’ll be a great critic and you’ll be able to get a sense for what types of clothes fit you, if there are colors that suit you well, etc. Take some notes so you don’t forget your dress shirt size or whatever a few months later. Buy your friend a nice lunch and thank her copiously.

Colors and fits are highly individual; you may find that a regular cut dress shirt fits you great or that you need to get something special to look good. You say that you’re overweight so big & tall stores would be worth checking out - I’ve known guys who were pretty hefty but they carried their weight well and wore clothes that fit them right and they looked mighty sharp, not like some dude who just got draped in a random 2XL.

Personally I hate khakis. They’re just too blah. Skip the khakis plus pale shirt plus navy blazer ensemble. A friend of mine calls it the Prep School Hell look. You can get brown slacks that look much better IMHO.

I think GilaB is right on option 3; dark slacks go great with a polo shirt as well as a dress shirt. Pick up a couple of ties (and learn how to make a nice knot!)…a lot of guys go with some pretty basic color palettes in the shirt & pants department and a nice tie gives you the opportunity for a splash of color. Clean dark jeans also go well with nice shirts and you can still add a tie to dress it up. That will cover your range from “casual” to just below “dressy” (I’d call matching slacks and jacket, shirt and tie to be “dressy” - your basic job interview outfit).

I’m not a fan of white shirts because they’re tough to keep clean - any little spot or stain, dirty collar, etc. is pretty blatant. Ditto with undershirts - Jockey sells packs of nice cotton undershirts in colors.

Taomist’s suggestion of a sport coat is good if you think you’ll be doing stuff where something more than just a dress shirt is needed. Some kind of warm sweater or jacket that you can wear with a dressier outfit is nice - doesn’t have to be pricey, I’ve seen pretty nice dark wool peacoats and similar for $50-$100 on sale. Good on a date where it’s chilly outside.

Almost none of this stuff will look good with sneakers, get some comfy casual-dress shoes. A good pair will last many years and can be resoled (I finally wore out a great pair of Eccos after about 15 years). Rule of thumb is that all the leather stuff should match - if you’re wearing black shoes have a black belt.

Random thought - if you think there are a couple of celebrities who look like you (either their face or their body) search for online images of them - you’ll probably find a bunch of shots from talkshow interviews, awards ceremonies and whatnot where they are dressing up a bit and you may get some good ideas. Here’s a couple of shots of Zach Whatsisname:

Dressed up (warning, flipping off the camera):

Informal but not sloppy:

If you’ve got a beard, keep it trimmed neatly. Whenever I see a raggedy dark beard on a guy it always makes me think of this dude:

Some large department stores (and many Macy’s) have a tailor who will adjust anything you buy in the store - not just suits - for free. Even if they don’t have it, a tailor is often not terribly expensive. Getting an outfit that fits you perfectly can often take it from “meh” to “wow.”

Other fashion advice - I’m a big fan of the vest look for guys. Slacks, a button-down, and a vest is just a sharp combo in my book, although I usually see it on super-skinny guys. You’d probably have to try a few on to see how it looks on your figure.

Don’t be a afraid of color! While black, grey, and blue are all perfectly fine, don’t be afraid to try on salmon, teal, or violet! Many guys would never think of trying on bright colors or pastels, and are surprised how good they look.

Whatever you do, don’t get something you’re not mentally comfortable in, even if someone else says you should wear it. You’ll feel awkward & self-concious.

I’m not a fan of khakis, myself - they look like part of a uniform to me (13 years of Catholic school, I guess), or they look like “casual Friday at the office”. For a date, I’d say nice, dark jeans, dress shoes & a good shirt are fine.

Fit is important. It’s not as important for jeans, but make sure your dress pants are the right length. Buy them long & get them hemmed if you need to, but don’t let them drag on the ground when you’re wearing shoes, or hike up above your socks when you sit down. Most department stores will hem dress pants for about $10, or most dry-cleaners can do it, too.

A beard is fine, but if it’s wild & woolly, get some trimmers to keep it neat. Many hairdressers can teach you how to trim it so it’s even & flattering. A good haircut will work wonders, too. You don’t need to use a ton of hair products or anything, but if you’re dressing up, you’ll want your hair & beard to look the part, too.