it all depends on your personal style and price range. some people like to dress up, with a button up, some khaki's and a pair of oxfords. Other people dress down like you with sweat pants/hoodie. Then there's something in the middle, which is where I'm at. For people who are just getting into clothes and fashion, I usually first recommend h&m and urban outfitters because they offer really basic stuff for pretty low prices. Around this time of year, i'd wear a hoodie or a flannel with jeans, khaki's or joggers. I'm pretty minimalistic--i don't like attracting attention, but a lot people who actually notice me give me compliments on my outfit. The thing that stands out most about my outfit are my shoes. A lot of them are "hyped" meaning highly sought after and pretty expensive. The shoes are the foundation of the outfit, so get some nice shoes you like. For someone whos just starting, I'd recommend a pair of black old skool vans because they go well with almost anything. don't let the cheap price tag fool you, travis scott wears them from time to time and he has great fashion sense. For someone who likes to dress a little more formally, I'd recommend chelsea boots, oxfords, or chukka's (no particular brand, because they all look the same). A lot of jocks/bigger/people from new york like a pair of timberlands, which is good for this time of year. I'm skinny and i don't think i look good in timbs lol, but maybe other people can pull it off For someone who likes to put themselves out there, I'd recommend some jordans or some "boost" shoes (made by adidas; it's been a growing trend over the last couple years mostly thanks to celebrities like kanye). some good boost shoes are nmd's, ultraboosts, or yeezys--if you have the money. I got my yeezys for $470, but few think it's actually worth the money, which is fine. For jordans, some popular models are the 1s, 4s, and 11s. with pants, the most important factor is definitely the fit--not too tight, not too baggy. It has to be the right length and size so that you get a "stacking" effect, which is when your pants are kinda long so they fold up a little bit. I would highly recommend buying jeans/pants from mnml.la or hyperdenim. Some higher end pants (if you care) would be from fear of god., or saint laurant , but theyre expensive (and sometimes really rare, especially f.o.g.) And then with the top--just wear whatever you like. I like to wear pretty basic stuff with no big logos or graphics. I have a few hoodies/shirts with just a logo, like adidas. Some "hyped" brands would be supreme, bape, palace, and antisocial social club. But for more basic stuff, check out tommy hilfiger, adidas, champion, h&m, and urban outfitters. Flannels and button ups can be bought from a local mall or something, brand doesn't matter much for those. I'm also a huge fan of accessories. They sound girly to some, but to each his own. I wear a bunch of bracelets , and a pair of fake glasses (i have perfect vision, but i look better with some wayfarers.) You could also spend some money on a gold chain (kinda hood imo), or a nice watch. don't get a cheap one though, people can sometimes tell a good watch from a cheap one. Hats are also a common accessory--dad hats, trucker hats, sports hats and beanies are pretty trendy tl;dr--as long as you wear what you genuinely like, no one's gonna judge you. just find your own style. Don't be a dickrider and try to dress like someone else, you'll look like a scumbag. Like how all frat guys wear topsiders and vineyard vines. The point of fashion is largely self-expression (on top of keeping yourself warm and hiding your genitals), so trying to copy someone else's style is counter-intuitive. Switching to a whole new style can be hard, so maybe try to change things up one piece at a time. hopefully this helped. i'm a huge fashion nerd, following dozens of fashion twitter and ig accounts so i keep up with the trend (mostly streetwear) and know some good brands. If you want more brand suggestions, i'm happy to keep you posted. also i don't have a playstation. i did this purely bc i like helping people with finding their style. GL bro