What Your Dress Shoes Say About You

Son, I been in this #menswear game. Understand, longwings are to #menswear what the Pro Keds 69er was to sneakerheads. I done read Bobbito Garcia's "Where'd You Get Those?" so don't act like I don't know my history. You wanna test the kid on wardrobe staples? My OCBDs been worn so often I got all the collars frayed. I rep my squad in a repp tie, and learned Japanese just so I could read "Take Ivy." Come at me. I'm the Osiris of this blog shit.

I was born with Quadrophenia. Anything British I fux with. Fishtail parkas? Duh. Crombie jackets and Harringtons? Got like ten. Grew my hair out to a Beatles mop top when I was seven, then bent it to the side like Beckham after puberty. Asked for a Vespa for a 16th birthday, and some crispy Ben Sherman shirts. Flew to Savile Row and studied abroad at Tommy Nutters, hoping to get knighted by Sir Paul Smith.

I am a recovering hypebeast. I really wanted to wear my Concords with my tuxedo so I could really nail that "Boyz II Men at the Grammys" look, but they got the veto from my parents, who said that they were inappropriate for a court appearance.

The only reason these got copped is because Mark McNairy's the shit and these were the only semi-affordable joints since they were on super sale.

I'm allergic to branding and everything else in my wardrobe is super minimal. I love designers like Jil Sander and stores like Uniqlo and Muji. Despite the fact that I'm a grown man, when I order at restaurants I make sure that they plate my food in a way that it doesn't touch each other. Or else I will straight up throw a tantrum.

I bought these because Nick Wooster wears them.

I know what luxury is. When I have to step out of the Rolls Royce, I switch from my velvet slippers into these—after I throw on my cashmere socks though. I'm the dude from Rick Ross' "London Skit." My bare feet have never touched ground that wasn't plush carpet. I have $200 house slippers for hardwood and tile. I was born with a silver spoon in my mouth and melted it down to make the bits on my loafers.

Everything I ever needed to know about style I got from the Internet. I had no idea what double monks were until I saw some dude on Tumblr really stunting in a pair. I knew I had to have them, and since then my life has been an endless quest for "sprezzatura." One day, when I stop buying so much expensive clothes, I'll move out of my parent's basement. Until then, I can stunt on herbs in the mall. See me outdressing fools in Hollister kits.

I cried for days after Ralph Lauren announced it was closing Rugby. Brooks Brothers Red Fleece held me down for a little, but it wasn't the same. When the Ovadia brothers showed their J. Press York Street line, I finally left the house for the first time in months. My pants have never met the tops of my shoes, and I have every color except khaki and navy. I don't have the balls to tell anyone to "go to hell," so I let my wardrobe do it for me.

Sorry, what were you saying about my shoes? I couldn't hear you over my piles of money. No, I don't read blogs. Too busy counting paper and looking at my stock options. Do you like apples? Cool, I have about 700 shares in Apple. How you like them apples? I'd pay more attention to style if I wasn't so busy being successful. Besides, I only wear shoes about three hours a day. The rest of the time I'm barefoot. On my yacht.