Off the Cuff - Carson Kressley [7]
In the summer, flip-flops are chic with absolutely everything—shorts and a linen shirt, denim and a blue blazer, khakis and a white cotton oxford. But feel free to wear them right into the fall, as long as snow has not yet fallen and the temperature is still mild. I once wore a brown Jil Sander suit (that’s a fancy lady designer from my homeland) with brown Old Navy flip-flops. But this look is not for amateurs. I’ll admit that flip-flops are hard to wear in the city and hard to drive in (see Driving Moccasins, below, for those occasions), but that’s part of the cachet.
5.The Cowboy Boot. The cowboy boot is a classic American icon, right up there with baseball, apple pie, and show tunes. Okay, maybe not so much the show tunes for you. But cowboy boots made America great, and they’ll look great on your feet, trust me. Go out and get a pair or I’ll kick your ass. Wear them everywhere: in your living room, to a game, to the Emmys, to the opera. They can go everywhere except weddings or funerals, unless a rodeo clown is getting married or has died. Then you’re in luck!
6.The Chelsea Boot. They’re called Chelsea boots because everyone in New York’s Chelsea neighborhood, where nearly everyone is gay, owns a pair, and gay men know shoes, people. Chelsea boots are compact boots with a side gore, which is a stretchy little elastic panel that allows the boot to fit snugly even though it doesn’t have laces. I prefer them in black, but brown suede is yummy, too. Chelsea boots are classics that go well with absolutely everything—they’re sexy and a little more rugged than your average dress shoe. And because they were invented for riding, they add just a little equestrian flair to your wardrobe. Trust me, horse people know clothes. It’s never a bad idea to copy them.
The Glories of Shoe Shopping
Here are some little shopping tricks For treats for your tootsies. First of all, you should try on shoes later in the day, because your feet tend to expand as the day goes on. And make sure you’re wearing the socks you’re really going to wear—no trying on dress shoes with big white tube socks. Most importantly, don’t get suckered by the cute salesgirl who tells you, “Don’t worry if they’re not comfortable now! They’ll break in.” Let me tell you a secret. “Break in” is a code word for “Not gonna happen.” Shoes should feel comfortable when you try them on. If they’re not comfortable when you buy them, they’re probably not just going to magically morph into comfortable shoes later on.
Finally, if while on your shopping journey you find a pair of comfortable shoes that you absolutely, absolutely love, and they are so “you,” and so great looking—go back and buy a second pair of the exact same shoe. Just like condoms, it’s always good to have a backup. Trust me, you’ll thank me later.
7.The Classic Tennis Shoe. I’m not talking about white Reeboks here. And I’m not talking about all these exotic colored sneakers that make you look like a refugee from the Namibian national soccer team. I’m talking about black, navy or natural cotton Converse Chuck Taylors, which look great with jeans or a suit. They’re always timeless and cool. Think James Dean. If Chucks don’t tickle your fancy, try the classic black-and-white Adidas sambas or a chic pair of suede Pumas.
Going Sockless
Going sockless can add a WASP-ish, care-free joie de vivre to your look. It’s so cool and has a trendy kind of sophistication. I often like to wear shoes without socks from Memorial Day through Labor Day, for the perfect summer chic casual look. But this is only acceptable in casual situations—for those easy breezy summer weekends when you’re on vacation or at the beach and it’s fun to wear a pair of jeans, a blue blazer, and a white shirt with loafers and no socks. Seeing the tanned tops of your feet can give you all the sexy allure of a Kennedy, without those pesky DUIs.
But going sockless is not for dinner at the White House or for a meeting with your loan officer. In fact, you