It sounds like you’re trying to build a wardrobe essentially from scratch. The thing you’ve gotta do is stick to classic clothes with minimal detailing and sober colorways. Walk into a store that has a lot of what I just described hanging in the window and start trying clothes on. you should be able to find these in any large European city.
what’s the base you’re building off of? how much money is a decent bit?
and while the whole ‘dress shirt into pants thing’ is ok advice, we need to se understand what you look like for what type of cut and if your body type fits that style. if you’re chubbier, you should probably go with a striped, less tight fitting dress shirt, usually sleeves rolled up with tapering pants, preferably black.
if you’re skinnier, euro cut single color, high weave with straight tight pants, any color.
P.S. If you want to look like a yuppie you can just cop a cheap button up, some dark black or faded blue jeans, add a fedora and you have an instant hipster look. You’ll have to top this off with ugly skate shoes or a pair or some disgusting colored converse high tops.
I’ll list things from least dressy up to most dressy
Polo shirt and jeans
bowling shirt and jeans (NOT to be confused with a short-sleeved dress shirt. Chicks hate those)
Simple dress shirt (light blue, possible small striped pattern) and dress pants-no tie
More formal dress shirt (solid colour, possibly black) and dress pants-no tie
More formal dress shirt, dress pants, and tie.
Take 2-3 lady friends shopping with you (incase the 1 you choose to help you has bad taste).
Alternatively, ask someone for help at a men’s clothing store.
some smart casual shoes, a pair of shorts, and a S/S button up
the smart shoes and button up will tell ladies you’re a man who gets shit done while the shorts and short sleeves say you’re still playful. Check out this steezy motherfucker,
probably needs a vagina swatter to keep all the bitches away
or how about something a little more forward? leather pants and an avant garde jacket to let everyone know hey, don’t even start talking about clothes to me, you don’t know shit motherfucker
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The above outfit is just an easy way to say “Why no ladies, I don’t have any testicles. I’m off to sip wine at an alternative-blue grass-screamo-trash-core lounge. After wards I shall organize my designer belt buckle collection by alphabetical order”
Shoes first, they’re THE most important thing. Don’t spare there.
A shirt THAT FITS WELL and is made of A GOOD CLOTH. Colors, patterns, type, are less important. Of course you need some taste there, which the internet can’t give you.
Trousers: see above. Denim is ok in my book, if it meets those criteria.
Don’t worry about how the fucking teachers will see you, worry about how you see yourself annd it’ll work great!
Oh, and about glasses, you want to look nerdy but sharp… hmmm… plastic colored frame. Bullshido blue or Bullshido red are all the rage nowadays.