If you had $500 to start a streetwear wardrobe...

I suppose he can't afford to blow all his money on high-end jeans. I'd budget for two pairs of sneakers, 1 pair Gap jeans (or whoever carries cheap jeans), 1 pair cargoes (I hate cargoes, but most people like them), and the rest on tops like tees and polos. T-shirts and polos can be had for $10-20 each at vintage shops. Vintage tees are much more individualised and you ccan save a lot of money on tops that way. Maybe spend the extra money on more jeans and more sneaks. $500 is not really that bad. If I had to restart my streetwear wardrobe with only $500 I think I can do fairly well.

Stolen bathrobe from a high-end hotel cheap flip-flops $500 pair of sunglasses

$100 leather jacket $50 jeans $100 shoes $20 belt $20 t-shirt $5 sunglasses So he could get two pair of jeans, two pair of shoes. maybe an extra belt, and a couple of more shirts or a sweater.

It's funny how people are approaching this - opportunity to be thrifty, etc. I guess it would help to know the personal taste/build of the wearer, but if I had the money... I'd say <$100 jeans (Levis premium, maybe, or non-crazy diesels, like these Zathans on sale at Nordstrom (they also have Levis Skinners and some odd Evisus on sale). I'm still curious about APCs, though, so that curiosity might win out, but I dunno if I'd want my only pair of jeans to be dry denim. $75-$100 on a track jacket from Adidas.com. In my opinion, you can't get a good enough leather jacket and other staples all for >$500. Maybe $75 kicks from there too, or something like these Varvatos Converse, which I dig. Can one in good conscience mix converse and adidas? Is a mix preferable to head to toe branding? Burning questions to keep you up at night. $100-$125 - Two tshirts, one "leisure shirt," one zip-up sweatshirt from American Apparel. $90 Liberty/PS shirt from Andrew Atlanta. Hmm. Not much room for accessories. I hope he has a GI watch and belt.

Why?

Maybe that would be best, actually - really force yourself to break 'em in. I don't own any dry denim - I'd like to - but the impression that I get is that these jeans require a significant amount of attention, and I'd want a pair of jeans I could throw on, throw in the washer when they get smoky, etc., assuming I don't have a backup.

A pair of APC Rescues (more versatile and easier to like than the New Standards). One pair jeans on discount - Check out Scoopnyc.com's sale. Comes to about $230. Four tee shirts (check out threadless.com for $15 shirts thast are pretty sturdy and some cool designs that won't break the bank.) that puts you at $300. Standard, versatile sneakers. I recommend the Adidas Samba or Samoa - goes with pretty much anything, and are $60. That is now $360 or so. Get a (real) vintage leather jacket - should set you back $70, max. You are now at $430. Get a hoodie (about $45-55 from American Apparel). You only have $20 left, but get him to splurge and get a Paper Denim belt ($70 on sale at Scoopnyc.com). Set, game, match. Only $50 over budget. Great starting wardrobe.

Rescues definitely.

2 pairs of classic shoes (adidas superstar (about $50-60, chuck taylor about 35-40 of ebay maybe even less) = 100$ 1 pair of dry jeans (APC rescues is a good idea)= $120 1 pair of levis 501 (of ebay) = $20 3 AA colored t-shirts = $50 (with shipping) 3 Threadless t-shirts = $60 (with shipping) 1 thrift store/ebay track jacket or hoodie = $25 1 thrift store/ebay denim jacket or leather jacket, depending on preferences/climate = $75 1 Belt (LAG is a belt guy we'll go with his suggestion = $70 This goes up to $520 and is pretty versatile. If he already has a cool belt (maybe a military one) he should get one more hoodie or few more t-shirts depending on the climate....

Military belts and boots would be way cool, plus he already has those items. Pair that with cargoes or something with lots of hardware and he can go for the faux-military look -- while having the legitimacy of actually being in the military.

i would assume that a guy in the military doesnt want to look military on his "days off" but if he doesnt mind then he's def gonna save some $ on stuff he already owns i have nothing new to add that hasnt already been mentioned but would re-emphasize that you can get lots of cool sportswear cheap on ebay if bang for the buck is an issue, and you got the time to wait for an item to end/bid/get it shipped to you. too bad UniQlo isnt a feasible option since those jeans are hella cheap and a better cost alternative to APCs. maybe he can get transferred to Japan

Military has very specific rules about not mixing uniform pieces with civvies. I have been there on this one.