Hey Hint,
I’m a pleasantly plump social chronicler and published author who’s becoming something of a boldfaced name myself. Lately I’ve been getting beaucoup calls from TV types asking me to pontificate on all things fashionable, but even though I’m tres gay, I don’t know what to wear! Obvi, I’ve got tons and tons and tons of chic friends, but I worry they might be lying when they compliment my look. Thus, I’m desperately seeking a figure-flattering, media-savvy ensemble that will take me from the UES to the LES to CBS to Boom Boom to the West Side Club without ever looking out of place!

Xoxo,
Gossip Girl

Hey Girl!
Haven’t we met somewhere? The Cock? Le Depot? Slammers? I think you look great just the way you are, but if you want a mediagenic new look, you might try these…

Moncler Gamme Bleu jacket: $1390
Straight TV audiences only take gay men’s advice when they dress like fools (see Jay Manuel, Richard Simmons and Dwight from The Real Housewives of Atlanta). The only other way to be a famous TV gay is to be a lesbian.

Comme des Garçons Shirt hat: $193
If your hairline is retreating faster than a Lohan at an NA meeting, so why not cover it up with a festive chapeau?

Lanvin cufflinks: $320
All the great gay writers need something that reminds them of their childhood. Proust had a madeleine, now you can have My Little Pony cufflinks.

Marc Jacobs shirt: $454
What better to wear while you’re kissing ass than a blouse covered with kisses?

Y-3 suspender pants: $783
You can stuff the table rolls from all those benefit dinners you attend in the cargo pockets and no one will ever be the wiser.

Hermès Birkin bag: $64,800
Sure, $64,800 is a lot of money. But you can be as big as a house and no one will say one fucking word about it when you have Birkin elbow and a diamond-encrusted croc bag dangling from your arm.

Sculptees waist smoother: $35
Not fitting into designer loaners would be too, too devastating for words.

Go Softwear padded butt brief: $30
Every bottom needs a lift.

Comme des Garçons socks: $39
“One does want a hint of color.” —Starina, The Birdcage

Giorgio Brato coral scarf: $182
A dramatic gentleman demands a dramatic scarf.

Pierre Hardy moccasins: $682
Why should your feet ache after a busy day of social climbing?

Cartier Love Ring: $800
Use those writing skills of yours and start an internet rumor that this pink-gold engagement ring is from a wealthy Latin American industrialist with a serious case of the closets who you only see once a month at the Carlyle. Voila! You’re ten times more interesting.

L.G.R. sunglasses: $389
Wear these to Sant Ambroeus for brunch and no one will know you’re eyeing the crowd or crotch-watching the waiters.

Grand total: $70,097
If your book royalties can’t cover it, just remind a few of your society girlfriends about those photos in your phone. You’ll have the money in no time!

Stay classy,
Roberto

Email your problem and picture to Robert. If he’s moved, touched or turned on, he’ll virtually style you in the best fashion has to offer. Also visit his blog, The Barr Code.