As requested my @maya here's some not-hard ways to not look like a walking hamper
  1. Make a base of neutral colors in your wardrobe
    Dark blue, grey, black, white, brown, olive. When in doubt these colors will flatter you and be easy to pull off. Then you can add bright pops of color
  2. Stop thinking you're not part of some "fashion world" or choose not to pay attention to it. If you wear clothes, you're in it
    Life is full of choices. Choosing the buy clothes at Bergdorf versus Old Navy is the same at the end of the day (allowing for some $$$ difference of course). You still project a look. And Zara and uniqlo copy and high fashion all the time. You don't need to look like Tom Ford but just know your pants and tees are a fashion choice and like most things you could stand to make more informed choices. Clothes make the man and do you want to be an Old Navy man?
  3. Treat your hair with intent
    I'm not blessed with good facial hair. A sage beard eludes me. But even i trim to keep it and the hair on my head in order. No matter what else you do, so long as your hair seems in order you will look like you have your shit together. Clean up your neck, come clean about that attempted mustache, and don't do whatever brad Pitt is doing. When you're that dreamy nothing really matters and he's just fucking around at this point
  4. Get better jeans
    Denim has become poopy in the past few decades. Blame the 70s and everything since. But it's back, baby, better than ever. When getting denim feel for some weight and heft. Big is selvedge denim but that can be a bit pricy, though worth it. If not that then just checked to see if it's stitched well. And for the love of god make sure it's all cotton. Whatever fit works for you works but if it fits snug at the butt it's probably the right size
  5. Your pants should end at your feet
    The pooling of fabric around men's ankles is a damn damn shame. Whether slacks or chinos or jeans, it's all crappy. For informal pants you can roll the cuff but just take them to a tailor and spend 10 bucks to look like a million
  6. With nice shoes most is forgiven
    Cheap leather, space age monstrosities, and blocky boxy shapes have turned men's feet into battlegrounds. Probably the easiest thing to do with shoes is just tone them down. Simple white canvas sneakers. Leather dress shoes with hard soles, not rubber. Suede! And if you're wearing flip flops more than 50 feet from a body of water you can treat yourself better
  7. Try crew necks as opposed to V and hoodie
    V necks are fine sorta but not really. If you must show off your surely rippling pecs then just get a button up shirt and leave the top two unbuttoned. If you get a v sweater have a real shirt, not a tee, underneath. And let's all give up hoodies as a crutch. They're shorthand for "chill unthreatening bro Everyman". Try a crew neck sweatshirt. Have a hoodie for good times, but you're better than that being your "outfit"
  8. Being overdressed isn't as big a problem as you think
    You've got some shitty friend who is like "whoa dude you're looking fancy trying to star in mad men or go on your yacht" or something that isn't funny and a refuge for "comedians" who get laughs from just being shitty people. You look great! Don't listen to them. People appreciate when someone looks nice or put together. Don't be afraid to stand out. You don't need to "peacock" or ugh. Just by doing simple things well you will stand out well
  9. Get a navy sport coat that fits, is softly constructed, and not part of a suit. Period.
  10. Have some fun
    You're lying if you don't find playing dress up a little fun. Look at photos of your idols. Mimic them. Then figure what you do and don't like and keep adding and subtracting until you got something that feels like your style. Try fun things. Wear linen. Get a sweet hat. Yes you can pull off that sweet leather jacket. Just remember- keep it well fitting and try to steer clear of childish things. Don't fall for trends. If it feels right, it is. Look good, feel good