What They're Buying: Nike for J. Crew Vintage Collection Challenge Court Sneakers, $98; Alden for J. Crew Indy Boots in Suede, $500

So you finally sold your precious collection of Jordans on eBay for just enough scrilla to move out of your parents' basement. They couldn't be prouder! Even better, you got enough profit to go buy yourself some real big boy clothes and not run around in the same BAPE hoodie and A.P.C. New Standards you always wear. Thing is, instead of the Ludlow suit you meant to buy for that job interview at McDonald's... you walked out with a New Balance collab, a Nike collab, a pair of Aldens, and barely had enough for a chambray shirt. Whoops.