Different clothes for different crowds. That said...
I NEVER wear khakis. Not interested in the husband-wrangling crowd.
I NEVER wear band shirts. Not interested in fake-a$$ hipster chicks who are buried in their fvcking iphones.
I RARELY wear tight jeans, it's more like slim jeans for me even, but even then... Only out at bars, because my friends like to go to bars, and only cause they somehow look dressier, but I have never found bar trash that I actually admired, so meh.. If I could kill off the tight jean trend, I would. It's a fad of the emasculated sector of society trying to be androgynous as if that were better than being masculine. Tight jeans say "I'm dressing nice but dressing casual, but not so casual that I'm not overtaken by my vanity, of which I am". Not a masculine feature.
I mostly wear solid-colored hemp shirts. The ones with a v-neck get more looks. I threw out all my band shirts, weird artsy shirts, because fitting into a label especially the hipster label is just going to make a girl come to a lot of assumptions as to what you're in to and what you're like. Hipster girls will dig you. I can't stand em past wanting to fvck them cause yea a lot of em are hot but have **** for personalities and are outrageous attention *****s. When you don't have logos or bands or sports teams on your shirts, a girl can't guess about your interests, you're a mystery, and the mystery will intrigue her, and she'll have to get to know you to guess anything about you.
Black jeans > blue jeans. Dark cords can work on the right person with the right button-up (not mini-plaid hipster ****). Don't wear shorts to a bar, club, party or dinner date, but always shorts for outdoor dates (going to the park, a lake, hiking, frisbee, w/e). Plaid shorts only work on bros, if you can throw the bro thing. Skater/punk types stick to darker cargo-style shorts. Don't get loud with the designs on shorts, which is hard, because for some fkn reason every store sells a billion crazy colored grid shorts and like one or two solid color shorts.
White socks are lame, and they get gross real fast. Ankle socks only with shorts, doesn't matter with pants. Gauges are a billion times more masculine than regular piercings, but they'll drive away conservative girls the same way tattoos do. From the varying responses I've seen, 3/16-3/8 gets the best response from girls. Smaller seems too much like regular jewelry and not hardcore or whatever it is that girls who like gauged guys admire in that, larger than that and their ears get gross, and only gnarly extreme girls are gonna chase that.
Black shoes look nicer, but they also make you look shorter. Sandals make you look like a couch-dad, unless they're chaco's, in which case you're an outdoor enthusiast, but it's weird if you wear those anywhere but outside or with a bunch of hippies and pot smokers. Nike's, Reebok, and most Skecher's look like **** and are worn by gradiently poorer basketball player wannabees. Vans and Etnies are the selection of skaters and pot smokers, pot smokers cause the wide foot option and extra cushioning's oh so cozy. Converse are a NO fkn hipster why do you still want to be 16. Pumas & Adidas have some nice, non-flashy tennis shoes. For anything classy though which should be any of your indoor one on one dates dont wear tennis shoes at all, get some good looking dress shoes that are plain, simple but obviously nice, unless the girl is a punk girl and also doesnt give a fvck.
Leather jackets work for some people, others it makes you look like a turd. Peacoats work with people who can sport facial hair successfully. Outside of those, your coats must look practical, not like a fashion statement.
Fedora hats are for hipsters and indie bands with no balls. However, they can be fun at a black-tie event. Just remember, only one fedora per group. Scally caps also require facial hair, otherwise you look like a newspaper boy. The castro-style hat peacocks well without being peacocky, in that people always mention it cause it's a rare hat, but it doesn't look bad or loud or flashy like most hats. Ball caps make you look like a red-neck or a sports fanatic, only good on cheerleader types or raised-west-side types, maybe cause it's nostalgic or some ****, but they don't look good.
That's my code of dress pretty much.
edit: You'll also notice a generational difference in this thread. People gettin rounding closer to 30 and older are going to be wearing more brands and button-ups, because you need to display that life has been at least successful enough to buy nice things to wear. People younger than that where established success with big savings accounts is more of a goal you're working toward while you party on the side are gonna slide more toward tees and jeans.
