I'm probably going to get shit on for providing a formulaic look, but APC New Standards (size down 2) Hanes T-shirts (or Uniqlo or Muji if you live in NYC) Gold Toe socks (or Uniqlo if in NYC, Pantherella or Paul Smith if you can find off of ebay or B&S) RM William Chelsea boots, Alden Chukkas, or Red Wing 8173s or Gentlemen's Travelers, or LL Bean Katahdins. Some shade of brown. White Chuck Taylors, Jack Purcells, Vans New Eras, Common Projects Achilles, Spring Court (personal preference), or Supergas That's the basics. You will want to expand with knitwear, coats, and jackets. This is where you will need to do your own research and look at the WAYWT thread at the top of this forum, the recent purchases thread, the Buy and Sell forum, troll eBay, and various online vendors and local department stores for sales. If you live in an Asian country, find a local tailor and get a dark navy or a charcoal suit made. Once you like the fit have him make a coat for you too. Research materials and cloth books after you meet up with him. If not, good luck. (If you want suits, forum affiliate Thick as Thieves provides a nice MTO/MTMeasure Yourself program online. Nice modern cut) But before anything I believe you need a haircut, better glasses (I like Moscot or Shuron), work out, and get laid. The last four I think are key to developing swagger and without it I think you will possibly become like forum user wagthesam. Make sure you get your measurements taken by a friend, yourself, or even a tailor before you buy online. Measure your best fitting clothes and compare with measurements people give you for the garment. Make sure the shoulder to shoulder measurements fit first, then look at pit to pit, then length. Sleeve lengths can be altered. Dress like above and you wont get mad rep here, but you will look a cut above your peers. Welcome to SF