Here's some of the decent looking Old Navy outerwear I was talking about. This jean jacket isn't exactly mind blowing, but does look alright.
This M65-alike isn't too terrible either, at least for $30.
This blazer also isn't too bad. Materials aren't going to be great (especially the "tweed" that's 40% wool and sounds utterly awful), but the design's ok, not particularly inventive.
Most of the rest of it wasn't any good, and fits at any of the three Gap stores tend to be precision crafted by third world sweatshop artisans to turn you into a box, but you might be able to size down to get a good fit. If not, you could always borrow a sewing machine if you don't have one. As for the Gap, I actually thought this sweater was kind of neat. It's horribly overpriced at 120, but you might find it for a decent price on sale.
This cotton/wool/nylon hoodie's alright too, though I can pretty much guarantee that you'll need to have the sides tailored in if you want any kind of a waist at all.
In terms of outerwear, most of the Gap's stuff is pretty dull. This is a copy of a Levi's Type 1 jean jacket, which is a design I've never liked, and the denim's probably not any good either.
This M65-alike is better, and actually is kind of a cheap copy of a W+H M65 from this season. Still, neither piece ever did much for me, and this one certainly less so.
In terms of jeans, the Gap doesn't really fare too well either. Worse, even. These slim fit selvage jeans look alright
, but at 100, I think I'd rather just find a 20 somwhere and get a pair of APC Rescues from Mauro. There's just no way they're worth what the Gap's asking right now.
There's a washed version of the same. That's just an even worse deal.
There are, to be fair, some slim, straight cut and boot cut twill pants that look ok. Hard to tell without trying them on; I don't know if they're worth $50.
And that really is the only stuff worth paying attention to at the Gap and Old Navy. It's not all bad, but if your budget is tight"” and, believe me, I know that's like"” you can still probably find better things else where. Watch stores like J Crew for sales. Comb local thrift shops for decent pieces. Generally, you may want to pick up a few things at the Gap like those slim twill pants or maybe a decent looking sweater, but you're probably better served in most cases by H&M in that price range and, of course, judicious shopping around at better stores during sales. Jeans are a bit more complicated, but you can find really nice jeans like Earnest Sewn on sale from time to time as low as 80-100, which certainly beats the shit out of anything the Gap offers at the same price. If you want to and can spend a little more, you can find APCs around 120 and cheaper Japanese Levi's reproductions around 150 (Samurai, Sugarcane, Johnbull). If not, H&M makes some pretty decent jeans for 20-50 (low quality, but they look nice and fade fast), and if you're in the NYC/NJ area, Uniqlo makes some very high quality stuff in the same price range if you don't mind more relaxed cuts.