Wardrobe overhaul

Monkeys, now that I’m no longer a scrub in college and have been making some money, I need ideas for casual wear / date night outfits. My wardrobe is extremely stale, and the fraternity bro attire needs to go. Time to start dressing like a man that is no longer on his parents’ insurance. 
What do you you wear to brunch? Nice dinners? Watches? Shoes?

Depends on where you live and who you hang out with. Margs with a thot? I'll wear a baseball jersey or Hawaiian shirt with neutral PFG shorts and white leather sneakers. Top 2 buttons always undone. I also wear a Lululemon headband if my hair isn't fixed. I can get away with dressing like this because I'm tall and decently attractive.

On a more serious note, polos work if you're in shape and have decent sized arms. Don't wear skin tight shirts, but ones that hug the arm enough to show off the tricep are solid. Find what colors accentuate your skin tone - I'm tan year round with dark hair, so I go with navy or dark grey pants and a white shirt of some kind if I'm not wearing the above.

Since fall is here, I'll go with dark jeans, a dark flannel, and a vest with dark brown chukka boots. Sometimes will wear black Chelsea's depending on my flannel and vest combo.A look that's more edgy is tan suede Chelsea's with black jeans and a white t shirt. This works if you're skinny or toned - don't try this if you're anything more than a little lean. You can go black ripped jeans and black shirt if you can pull it off - problem here is jeans have to be tight and I hate tight clothes, but hoes w daddy issues love this look.

Long sleeve shirts with sleeves rolled up should be a staple of your wardrobe. Get those forearms thicc and veiny and roll those sleeves up.I'm in the south so I'll wear suede loafers no socks, dress pants cut above the ankle, and a tailored sport shirt w button collar and sleeves rolled up if I'm tryna look nice. 9 times out of 10 this puts me in the best dressed category when I'm out with friends.

Best advice I can give is get in shape - don't have to be shredded or massive, but getting an athletic frame makes all clothes look better. Then keep it simple with darker bottoms and lighter tops, preferably long sleeve. Wear solid colored shoes - I have black Chelsea's, suede light tan Chelsea's, white leather sneakers with a tan suede part, all white leather sneakers, and suede blue loafers. Belt should match shoes except for white and suede. Usually go w brown belt as it's more casual with those. I know I said a lot and it could've been much more concise but I enjoy typing my thoughts out as a whole and going back and seeing how it came out

You use a ton of words to talk, I’m amazed.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee

Solid, thanks for your thoughts. Luckily I’m in shape and have great forearms, so I love wearing shit that accentuates this..rolled up shirts should do the trick.

what about logos on polos? I bought some nice brooks bros pique slim polos but wasn’t too sure if the small breast logo was a no go

Fit comes first, regardless of clothing. Burn that into your mind. Im 27, for reference. 

For fall/winter:

Get yourself two pairs of boots: 1 black, 1 dark brown (never go light brown), invest a bit here.

Personally I like turtlenecks, but that's not for everyone. Generally, layering some knitwear (I like cashmere, merino wool will do too though, problem with those is that they are often pretty flimsy) will do the job (you can either go t-shirt or shirt underneath, depending on occasion/what kind of chick you want to bang) 

Get a navy/black wool coat, preferably with soft shoulders (personal preference here, structured shoulders are a bit too "old" for me, I don't want to look like my grandfather). Then get a parka for really cold days (try to find something with discreet branding, Woolrich has some decent pieces here). 

And finally, get yourself some twill chinos for winter, and chinos for fall. Or jeans, but I personally don't like jeans. (I own about 8 pairs of chinos and 2 pairs of jeans lol)

Take your Time and buy the peaces one by one. Don't rush it. 

There are also a lot of other things you can dip your toes into, such as denim jackets, overshirts, vests. etc 

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