From what I've seen, people associate brand names with style. What I mean is that people see your name brand clothes and even if you put together a sh*tty looking outfit they'll still think you're stylish LOL.
That being said I don't buy into the name brand hype. The bulk, 99%, of the time "name brand" clothes are of no better quality than affordable department store clothes. The only thing that makes them "better" is an inflated price tag, a logo, and maybe a sew-on emblem. Oftentimes I loathe name brand clothes as they're often over done with logos, making the wearer look like a walking billboard.
However, I do own several name brand clothes. I think the reason people prefer them is they are often on the edge of what becomes popular in an area. Name brand stores tend to get the new styles first and then department stores stock similar items a few months down the road. It comes off a little bit "poser" and oftentimes when a department store starts to stock a new style it's already fading out and being replaced by the next biggest thing.
All in all, buy what you like and what looks good on you. Unless people check the tags on your shirts they'll never know how much you paid for it (assuming it looks good on you). Don't fall into the old 'wear our clothes or be unlovable forever' bs that marketers push on the public.
As long as it looks good on you no one will know, or care, what brand it is or what it cost.
How old are you/ the chicks you go after? It has a huge bearing on the answer you seek
