You Wear The Same Thing All The Time
Despite your many clothes, you find yourself drawn to only a few things that you wear the hell out of. The idea is that you should have a well-edited closet of versatile gear that you want to keep rocking, so if you have a lot of stuff, and wear less than half of it, get rid of the clothing that's collecting dust (better yet, donate it for a totally sweet tax write-off), and take a look at the pieces you're rocking on the regular.
You'll probably notice a pattern, maybe you tend to flock towards navy blue, always wear Jordans (like Drizzy up there) with everything, or button-down oxford shirts are your thing. Don't go overboard in bulking up on these items, but it gives you a good idea of your personal style: the kind of stuff you put on for any old day, without thinking too much about it. Build the rest out from there, and you'll have a few cool outfits in your rotation.