Purely anecdotal statistic: 97 percent of dudes who wear boat shoes don’t own a boat. Docksiders remind me of puberty (slow dancing with boys with sweaty palms). Unless you’re a tattooed graphic designer with emotional baggage and a heart of gold. Y-O-U can wear these lorum ipsum typesetting-inspired kicks—an inside joke this mag editor might just adore. Band of Outsiders for Sperry, $150 at Nordstrom.
True confession: Flip-flops turn me on. These classic thongs say you’re carefree, romantic and cute; probably read Raymond Carver and write (bad) poetry while drinking Red Stripe. You may be too young for me. But who cares? You’re great at making out and have front-row tix to My Morning Jacket at Merriweather. Let’s fall irresponsibly in love—and get hitched on the beach. Leather Rainbow sandals, $51 at Cohen’s Clothiers.
Your mom and sisters spoiled you rotten—you grew up reading (and drinking) their Cosmopolitans. Something big made you drop out of law school and start your own nonprofit. And I believe it when you say you’re now less rogue and more Mr. Darcy. As you walk me home, I imagine kittens flinging themselves out of trees into your capable arms. Bethune 3 by Robert Graham, $268 at Nordstrom.
Coral drivers point to a country club type who’ll whisk me away for a weekender in Nantucket. A toe-headed charmer who’s good with numbers, you work in finance but like to play the ponies. Republican? Likely, which may prove problematic. #ReadyForHilary. I’ll end up dating your grown stepson (Marriage No. 2) and doing Pilates with your first ex-wife. Broadway by Marc Joseph New York, $165 at Hyatt & Co.
I should be rolling my eyes, but can’t resist, when a jet-setting foreigner shows up in “flight-risk” loafers. It starts on the dance floor where you sweat just one glorious bead—and ends in your hotel room, which smells like swagger and Tom Ford EXTREME. Staring at your chiseled face in the morning, I can’t help but think, “God, we’d make such perfect babies.” Wait, is that accent fake? Donald Pliner Dacio II, $288 at JS Edwards.
NB man-boys are a little OCD like they just vacuumed the suede and will cry if it’s scuffed. (Don’t you have 47 pairs at home?) You’re playful (if pouty) and give good witty banter. You wear gingham boxers to bed and named your pitbull Manny Machado. I often wonder when you skateboard off to “work”… are you actually at Soundgarden pretending to be a record exec? New Balance 574, $150 at Nordstrom.
>> Read more stories from our summer Men’s Issue.