In 2004, actor Joseph Gordon-Levitt brought to brilliant, heartbreaking life unrepentant teenage gay hustler Neil McCormick in the Gregg Araki-directed Mysterious Skin. Now granted, perhaps not the most obvious choice as a Fashion Icon, but I ask you honestly: Is there anything sexier than an angel with a dirty mind?

Of course life on the mean streets isn’t all Fruit Loops and riding in cars with Michelle Trachtenberg—it can be a tricky fashion row to hoe: You’ve got to stay warm and look cool at the same time (see #3), you’ve got to always be ready (see #7), you’ve got to have faith (see #2) and you need to walk away from any situation smelling like a rose—or even better, white pepper, ginger and vetiver (see #11).

While I thankfully never played little league with an overly friendly coach, I did survive that childhood hell known as Boy Scouts. So with that in mind, I offer you one last piece of advice from the bottomless black hole where my heart should be: Always be prepared (see #9).

The Seen:
1. Western denim and leather vest from Stolen Girlfriends Club, $398, idontlikemondays.us
2. Three Saints charm necklace in matte black, $29.99, timoteo.net
3. Kill City waxed denim slim fit moto jacket, $159, shop.alterbrooklyn.com
4. 5-pocket skinny jeans in over-dyed black by Cheap Monday, $75, revolveclothing.com
6. Brileigh textured leather belt by Diesel, $150, store.diesel.com
10. Dr. Martens Alfie Boot with canvas upper, $69.99, journeys.com

The Un-seen:
5. Super low sport brief by Timoteo, $22, timoteo.net
7. 2-piece horseshoe cockring, $69, myhardwear.com
8. Blue Crown 6-pack ankle socks, $11.99, tillys.com
9. Benchmade Harley Davidson Levitator money-clip/pocket knife, $50.99, cabelas.com
11. Gucci Pour Homme EDT spray by Gucci, 1.7 oz., $49.95, perfumespace.com