Frank's Dream Date: Shopping With Isaac Mizrahi

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You know Frank—he's been writing about menswear, sales, television, new shops, the recession, Lisa Loeb, the Golden Girls and getting blasted for Racked for almost two years. Well, we think it's time you got to know him and his quirky-irreverent views on life and fashion even better with his column: Love, Frank. Taking the form of an open letter and always signed with love, Frank will rant about whatever style-related conundrum he encounters in a given week. So buckle your two-toned leather Moschino belts, folks, it's going to be ? Something.

Dear Isaac Mizrahi,

Certainly you've found yourself amongst friends and engaged in a spirited, wine-fueled discussion of who-what-why hypotheticals. Brunch with Sandra Bernhard, perhaps? A movie night at Naomi Campbell's?

Things get a little messy; a little fuzzy; and people start getting really real. No holds barred, right? Who would you marry? Who would you kill? Who would you sleep with? With whom might you go apple-picking? No rules, no judgments, they can be living or dead, still-famous or way over?a conventional choice (Ryan Gosling) or, well, someone less so.

At my last such discussion—Sandra Bernhard couldn't make it—your name was brought up.

By me.

Because, I mean, Dream Shopping Date!

I can't imagine a more fun shopping buddy. And, like, we'd shop for everything. We'd have a full day.

I imagine we'd meet somewhere sort of uptown. It's a Tuesday because weekends are a mess, and we convene at some little bistro or something—one you just love—for a light lunch and some sparkling wine at noon-ish. From there we hit Madison Avenue on foot. We shop cashmere scarves, leather pouches, imported cheeses, chic pet accessories, monogrammed stationery and Tom Ford—all while talking a blue streak about cooking and fashion and the glory days. (Sample subject: Todd Oldham.)

We might stroll through a swath of Central Park, poke fun at tourists over not-quite-cold-enough Diet Cokes and some of those toasted nuts that always smell much better than they taste (not that they ever taste bad), before the requisite stops at Barneys and Bergdorf Goodman. We'd touch upon sunglasses, ceramics, artisinal chocolate, coffee table books, Marni, men's furnishings and Dries van Noten.

From there we'd be whisked downtown in the car I imagine you'd have waiting for us. My dream of dreams is that it's a valet-parked drop-top Mercedes and you zip us south as we gossip above a soundtrack of, oh, I don't know, Lisa Loeb and Dusty Springfield and Heart. It's autumn so we have the heat blasting to compensate for our roof-less-ness. Our sunglasses (new) are large; are scarves (also new) are flailing. But, I suppose it'd be fine if it's just a Town Car or whatever.

We park in the West Village, maybe we grab a quick cocktail somewhere lowkey. Then we'd do it all over again: Charming gift wrap, vintage pornography, some cute little nothings at Marc Jacobs, pastries and porcelain and pashminas and Pucci and antique tableware and fancy linens and quirky cookie cutters and fresh flowers and, I mean, everything.

Just everything.

Finally, exhausted, exhiliarated, we'd go to some little hole-in-the-wall trattoria where the staff knows and loves you (who doesn't love you?). There would be lots of red and chipped carafes and unfussy Italian dishes and we'd just gossip for hours. You'd give me your version of New York fashion history circa the last 20 years. Calvin Klein at his most drugged up; John Barlett at his most egomaniacal; Simon Doonan everything and everywhere; Michael Kors not just wearing black tee shirts every day; Marc Jacobs with his sense of humor and his love handles in tact.

It would be a wonderful day. And we'd end up right where I started: Discussing who-what-why hypotheticals

Anyway, now that I've utterly terrified you—carry on!

(In the off chance I did not terrify you, call me!)

· Love, Frank [Racked]