So I imagine this is going to turn into a huge thread, both decrying the innefficiency of wasting time worrying about clothing, and also people that are very adamant about some brands and styles and political/social implications of all this.

But I need to update my look. Or at least, dress a little better. I guess most of my life I’ve had two three looks:

  1. At work/business. This is basically any time I need to look halfway decent. I have pants, slacks, khakis, 2 sport coats, a bunch of dress shirts. Basically your “professional lite” work wardrobe. Lots of collared white/blue shirts.

  2. Not at work/just hanging out. This is what I usually change into when I get home from work. Or what I wear when I’m just going shopping or don’t have to care about what I wear. I mean, it’s not sweatpants, but it’s pretty casual. Whatever the cheapest jeans I can find are, (like Old Navy straight relaxed fit for $15). And a cheap tshirt (Old Navy sometimes has them for $1-$3 on sale and I can pick up 4-5 that way). Or Target has cheap ones. I’ve always had this idea of never “branding” so I wear just solid tshirts or ring tshirts.

  3. Going out/party/Vegas.

I don’t what to call this other than my “going out and want to impress someone” look. It would be like if you were going out to a nice dinner, or to a club in Vegas with your buddies, or to a cool party, something like that. For me that used to be pretty casual like jeans and a dress shirt with sneakers but now it’s more like a sport coat and a dress shirt untucked with expensiveish jeans. Like a sportcoat I get at TJ Maxx for $20 and pair with a dress shirt from there ($14) and a pair of jeans that are about $60. Sometimes I put crap in my hair, the only time I do is when I’m in this “wardrobe”. Comfortable dress shoes usually.

  1. A bathing suit in the hot tub. Just kidding.

Anyway, what are people’s ideas on clothing/fashion? So many girls have asked me to “let me go shopping with you, and I’ll pick out lots of clothes for you” or “throw that damn 20 year old holey tshirt away!” that it seems like I need a new style.

For instance, I went to an outlet mall with my girlfriend and got some “Marc Echo” clothing which has a rhino on it. A hoodie and a graphic print tshirt. I only know what Echo was because of Test Drive Unlimited. I didn’t recognize half the brands at the mall.

I buy my T-shirts only online. I don’t own a single T that hasn’t been purchased from Teefury or Shirt.Woot or an online retailer.

Jeans. Lots and lots of jeans.

I have a couple pair of khaki’s and some polo’s. Only one “nice” ensemble; Sweater vest with long sleeve dress shirt and a pair of matching pants.

Otherwise, I dress every day in the same thing; Jeans, T-Shirt, and a hoodie. Day in, day out.

Why don’t you just do this?

My husband picks one brand for which he knows his size and fit for all articles of clothing (boxers, socks, jeans, t-shirts, dress shirts, suits) and buys everything he needs (i.e., all of the above) from their outlet store once every 5 years or so. His mated buddy has his girlfriend do his clothing shopping for him. His single buddy buys things online and sends them back when they don’t fit or he doesn’t like them.

I feel like there is a strong chance you are asking this in the wrong place.

Yeah, but is this more properly a Hardware or P&R issue?

I know, but every time I do that, I see how expensive all the name brand/marketed stuff is. It’s so damn expensive, and for no reason! I can get 5 $5 tshirt from Target or Old Navy for the price of one $25 say, Abercrombie tshirt.

This, except Thinkgeek is where I get most of my t-shirts.

I am also 10-12 years older than Demon, but my proffessional career doesn’t hinge on me wearing a sport coat, thank fucking god.

I’m firmly in the “adamant about social implications” camp. Helping you update your look isn’t going to be the easiest task via message board.

Is there a budget? What’s your body type? How old are you?

Budget: Under say, $5000. I’m of average body type. 6’4" 220. Tall, not as lean as I used to be but not bad. 38/34 pants (hopefully soon down to 36/34). I’m 35.

Man, I sound like a girl.

Your fashion isn’t too bad given the fact that DC is a fashion zone disaster area.

But it’s time to step up from Old Navy a bit. Hit Banana Republic or some other equivalent and lose the dress shirt/jeans combo. Grab some cords, some black pants and polish up. If you want to look good, limiting your self to a $50 wardrobe is silly.

But to echo fire, have your women take you shopping. You’ll look a lot better than if you did this yourself. And I theorize that a large percentage, if not an outright majority, of married/pared off men outsource their fashion to their partners.

And so that’s why you look better when you are dating someone seriously/married. Your SO throws out all your bad shit and makes you buy new stuff. It’s kinda fun! Except I have a drawer of tshirts I will never throw out. Never!

I most certainly do, and as a result 90% of my wardrobe is made up of polo shirts and sweaters. She has a much better eye for fashion than I do.

You might actually be surprised at how much more comfortable the expensive stuff can be.

Given the choice between a $5 Old Navy t-shirt and, like, a $30 t-shirt from Lucky, I’m pretty much always gonna pick the Lucky shirt. They look nicer, and they’re made from much softer and cozier cotton.

Same’s true with jeans – once you start wearing the higher-end stuff you may end up wondering how you ever thought the Old Navy jeans were comfortable.

I still have a bunch of college party tees and concert tee-shirts I have. They’re just more in a milkcrate on the top shelf of a closet than being pressed into service. I’m a bit scared to wash some of them these days.

But most likely you shouldn’t be wearing t-shirts these days unless you’re doing sports or schlepping your kids around.

I am, ironically, much in the same boat as El Guapo here. I tend to stick to the theory that for my job and pay grade, they get the Target version of Business Casual - that being "No one item of clothing should cost more than $25 (not counting shoes). The notable exception being when I have to wear a suit, because I tend to be very proud of the fact that I wear a suit well, so I tend not to skimp there.

When it comes to what you actually wear, though, only worry about brands if you are trying to impress the kind of people who are concerned with brands. For example, if you’re wearing Ed Hardy, Abercrombie & Fitch, or Affliction - that’s only going to flag on the radar of the type of folks who are specifically looking for those things. Also, you will be effectively wearing a blinking sign saying “GIANT DOUCHEBAG”.

There’s a saying that goes “It’s not what you wear, it’s how you wear it” - but that’s only partially true. If you’re going to wear something that’s a few years/decades out of style, make sure it’s a look you can pull off that says “iconoclast” as opposed to “sadly out of touch”.

Also, do not try and save money by buying the cheapest stuff off the rack, rationalizing that it all looks the same. Quality of fabric will affect everything from how it fits to how it withstands washing to how long it lasts. Depending on your frame (and from all photos, Guapo, you’re pretty just Joe Off-The-Rack Average), you want to get a cut that will hang well and accentuate features you want accentuated.

No guy is well-served by clothes that are too tight, unless your name is “The [Something]”. See Disclaimer of Douchebaggery above. But in the same token, if you’re dressing in formless baggy clothing, you’re liable to give off the vibe of “college student that doesn’t do laundry often”, a sort of overly-casual vibe that you’re a bit too long in the tooth to be going for nowadays.

For just “hanging-out casual”, what often works best is a comfortable short-sleeved button-down shirt, spread collar (do NOT wear buttoned-collar short-sleeved shirts unless you are a cubicle-dwelling IT monkey) with khakis or shorts depending on weather and whatnot. Clean jeans can also be subbed in for khakis depending on company.

But all that aside - the best specific suggestion I could give would be that when you go shopping, take along a platonic female acquaintance whose opinion you respect, and get her opinion - but don’t discount your own. If you feel uncomfortable or unsure about a certain style, that’ll come across in how you wear it - sort of like how about 70% of men look awkward in a suit because they’re not accustomed to wearing one.

Have a look at ‘the sartorialist’.

Every summer and winter I go through his archive and get ideas of what I think would work on me.

So the real thing is, you can’t just have someone buy you new clothes, except as a Band-Aid. If you actually want to dress in a stylish and expressive fashion, you need to know something about the topic, and read up on fashion shit on a regular basis, the same way you might read up on graphics cards or WOW or whatever.

Because it’s not just a matter of what your frame is, there’s also the question of what you’re trying to say with your clothes. If you’re trying to look like a mature sophisticated dude, you’re going to wear different clothes than if you’re trying to look like an eclectic indie-music loving vegan or a relaxed outdoorsy guy or someone who’s really into graphics cards and WOW. There are actual choices for you to make here, and dressing in Old Navy t-shirts is kind of making a lot of choices by default.

So when people are saying “find a woman to buy your clothes,” they’re implicitly assuming that you can’t/won’t do this, and that a random woman will already be doing this. Which seems both a bit sexist, and a bit pathetic on the part of the dressee – maybe your mom can dress you! – but hey. I don’t really have any interest in reading about fashiony stuff either, so not like I can blame you.

I am going to start picking fights in here pretty soon.

This is super-important, yeah.

I also think that most men look awkward in a suit because they don’t like suits or shopping for them and therefore bought a cheap one that’s poorly made and doesn’t really fit them from some quantity-over-quality shithole like Men’s Wearhouse.

Anyone honestly suggsting that your wardrobe could be best supplimented with shirts that have ironic phrases on them is not really your friend.

Also, dude, not all jeans are made equal. Seriously. I know you have no reason to believe me here, but when I was younger I wore store brand jeans all the time because of how cheap they were. From Wal-Mart I’d get Wranglers and from Sears I’d get … what, Roebuck’s? Lee’s? I forget. Anyway, I figured they were all the same. Then a friend bought me a pair of Levi’s. Holy shit, they were so much better. Worth every extra penny they cost. Then a couple of years ago mmalloy got me a pair of jeans from the Gap and they were so much better than the Levi’s that I now find myself wondering if back in the days of Wrangler I wasn’t wearing the jeans version of a hairshirt.

Spend money on better jeans and feel better.

Also, wear World’s Softest Socks. I wear nothing but and anyone who doesn’t understand why obviously has never tried a pair.