Preppy Guy Candy

Chuck Bass

By Natasha Burton

With this sly and mysterious Gossip Girl hunk strutting around in a well-tailored suit, prep school never looked so good. XOXO, indeed.

Nacho Figueras

Of course Mr. Bass isn't the only man who can pull off the preppy look effortlessly. Ladies, drink in this sexy polo player and Polo Ralph Lauren model and just try not to wish you could stomp his divots. (Wink!)

Ralph Lauren

We can't ignore the man responsible for creating a look we love so much. Thank you, Mr. Lauren, on behalf of women everywhere, for allowing men to achieve the supreme quotient of hotness. And good for you for looking so darn cute in that paisley ascot.

Hunky Model #1

Preppy men, like this Lacoste model, aren't afraid of color. We wouldn't mind hopping on the yacht and sailing over to Hyannis to summer with this fine gent. (As every preppy knows, "summer" is a verb, after all.)

Hunky Model #2

What we love most about a man who can rock this style is how effortless, yet sublimely gallant, he seems. In case you didn't know, we must divulge that there are many perks to having a preppy boyfriend or husband, the most important of which is that you get to borrow his sweaters, essentially doubling your wardrobe.

Hunky Model #3

And this more dressed up look isn't so hard on the eyes either. We envision walking on this man's arm en route to a lovely dinner in Provincetown, Cape Cod. (And we can't help but imagine how we'd pair that oversize blazer with some dressy shorts and heels when we get back to the city. ...)

Tommy Hilfiger

Slippers on the red carpet are a definite "do" in the preppy world. And we certainly wouldn't mind popping over to Nantucket to hang with the Hilfigers — along with some of this designer's male models in tow, of course.

Tom Ford

Another designer who embraces the prep, albeit in a more Upper East Side than Nantucket way, is this bow-tie-rocking gentleman. Seriously, what is it about a guy in a well-tailored suit that gets us all hot and bothered? Men should be required to wear them at all times.

Patrick Robinson

Here's another one of our favorite designers sporting this classic look on the red carpet. We'd gladly be the accessory (read: arm candy) to Patrick's super sleek and sexy style any time.

Joshua Jackson

It's not just fashion gurus who are giving those good 'ol ascots some action. We much prefer this debonair style to the laid-back, chest-hair-showing look of some celeb men. (Looking at you, Rob Pattinson. We love you. We love your chest hair. We'd just rather see it in private.)

Kyle McLaughlin

We can't look at this actor without thinking about his Sex and the City character, Trey. Seriously, does a name get any preppier than that? Wait, don't answer that just yet — Biff, Chip and Tad totally one-up Trey.

Roger Federer

He may not be winning any trophies for his style, but if life was a U.S. Open, we would happily bestow Roger a silver gilt cup for his Edgartown-appropriate look. And then we'd request to sit court-side at his next match, so we could ogle him properly.

Carlton Banks

It's hard to believe that, not so long ago, the preppy look was portrayed as more silly than sexy on the hit TV show The Fresh Prince of Bel Air. (And, instead of swooning over him, the ladies full-on ran away from poor Carlton and his sweater-over-the-shoulders style.)

Prince William

Oh, how we love a man in uniform. If anyone can pull off all white — before and after Labor Day — it's this Brit.

Prince Harry

The younger prince is quite the looker as well. We sure wouldn't mind hopping on the back of his horse and letting him ride off with us into the sunset. (Though, that would probably put quite a damper on the polo match.)

President Obama

But it's not just British royalty rocking this classic style — our very own President Obama looked quite dapper during his jaunt off to Martha's Vineyard this summer. (And Michelle looked gorgeous, too, as usual.)

Jay Gatsby

A gallery of hot preppy men just wouldn't be complete without this famed novel character, portrayed by Robert Redford in the movie adaptation of The Great Gatsby. A mustard-colored tie never looked more dashing.

F. Scott Fitzgerald

Of course, we can't forget the man who gave us a glimpse of upper-crust prep culture in his famous book. It appears that Mr. Fitzgerald was quite the proper gent himself with that tailored suit of his. And now if you'll excuse us, we've got a party to attend in East Egg. ...