woman trying on a hat in a peplum skirt

Photo: William Garrett

Peplum Skirt
There's a lot of flounce for the ounce here, so select a soft material. "Stiff peplums look too Dynasty," says O creative director Adam Glassman.

How to Wear It: Embrace the skirt's femininity by choosing a sexy peep-toe or strappy heel.
If You're Short: Avoid wedges—they visually shorten your legs.
If You're Tall: A wide belt is an unexpected, chic addition.
What to Avoid: A full top that obscures the peplum. And no boots, stiletto or otherwise.

Blouse, Tucker by Gaby Basora, $298. Skirt, Eva Franco, $195. Hat, Kangol. Cuff, Kenneth Cole New York. Belt, L.K. Bennett. Shoes and clutch, L'Wren Scott.

Shot at Goorin Bros. Hat Shop, New York City.

woman wearing full skirt carrying flowers

Photo: William Garrett

Full Skirt
A voluminous skirt hides larger thighs and makes your waist look "tiny by default," says Adam.

How to Wear It: A fitted top always works, though a chunky sweater is a fun alternative. Full skirts look especially pretty with pointy flats and kitten heels.
If You're Short: Match the color of your tights to your heels.
If You're Tall: Anything shorter than knee length looks juvenile.
What to Avoid: Boxy tops and full coats and jackets.

Sweater, August Silk, $68. Skirt, Eva Franco, $320. Purse, Marc Jacobs. Ring, Anna Pellissari. Watch, Michael Kors. Bangles, Varelli and R.J. Graziano. Tights, Express. Shoes, Sigerson Morrison.

Shot at FleuraMetz, New York City.

woman in changing room wearing trumpet skirt

Photo: William Garrett

Trumpet Skirt
"This style shows off the derriere, so you need to be comfortable playing up your curves," Adam says. The skirt can also help build up your rear view if it's on the flatter side.

How to Wear It: The top—whether it's off-the-shoulder or more fitted—needs to come in at the waist. Nothing should be loose or untucked.
If You're Short: Make sure the hem doesn't dip below the knee, or you risk looking "too flamenco dancer," says Adam. "The rule of thumb when it comes to hemlines? Petite women look best in skirts that hit just above the knee; taller women should wear knee length or longer." And no matter your height, choose skinny heels.
If You're Tall: Have fun with patterned tights and seamed hose. "Think Sophia Loren in Rome."
What to Avoid: If you want to wear a jacket, make sure it ends around the waist, no longer. As for shoes, avoid any style that ties around the ankle (too cha-cha!), boots, and wedges.

Bra, Chantelle, $78. Skirt, Etro, $1,547. Shoes, L.K. Bennett.

Shot at Maison Kitsuné, New York City.

woman in trumpet skirt carrying a birthday cake

Photo: William Garrett

A Rule of Thumb
"The trumpet skirt is a lot of look on its own, so keep everything else simple," Adam says.

Jacket, Raoul, $295. Skirt, Nanette Lepore, $298. Ring, Alexis Bittar. Bag, Victor Hugo. Belt, Ann Taylor. Stockings, Spanx. Shoes, Vince Camuto. Cake: Signe Sugar; SigneSugar.com.
woman looking at a record wearing a maxi skirt

Photo: William Garrett

Maxi Skirt
"I love the maxi for day," says Adam. It's a very fashion-forward look." But the skirt needs to be long enough—it should be no shorter than half an inch from the bottom of your shoe.

How to Wear It: Choose a style that is streamlined but has some movement, and pair it with knits and booties or menswear-inspired flats.
If You're Short: It may seem counterintuitive, but a long skirt can make you look taller. Make sure the hem of your top doesn't hit much lower than your natural waistline.
If You're Tall: Experiment with layered tops, like a sweater and vest or loose, diaphanous tees.
What to Avoid: Pointy stilettos, knee-high boots, or anything too dressy. "Rugged shoe styles are fresher," says Adam.

Sweater, Twelfth Street by Cynthia Vincent, $325. Blouse, Marciano, $168. Skirt, Moschino, $895. Belt, Longchamp. Boots, Boutique 9.

Shot at Rebel Rebel, New York City.

woman in midi skirt with baby

Photo: William Garrett

Midi Skirt
The freshest—and hardest—style to wear, the midi isn't for everyone. Lengthwise, it should hit anywhere from three inches below the knee to midcalf. "It's really easy to get costumey with this skirt, so be careful," says Adam.

How to Wear It: Tuck a blouse into a high-waist midi and pair it with ankle boots. The midi is also great for those with longer torsos, because the length will balance your upper and lower halves.
If You're Short: Unless you're wearing a longer skirt for religious reasons, you should avoid this trend, says Adam: "A midi will just make you look shorter."
If You're Tall: Wear it with menswear-inspired brogues. "They're cool and unexpected with skirts," says Adam.
What to Avoid: Midcalf or knee-high boots—a proportion nightmare with this type of skirt.

Cardigan, blouse, and skirt, L'Wren Scott, $1,990, $1,025, and $1,025. Belt, Gap. Stockings, Assets Red Hot Label by Spanx. Shoes, Fratelli Rossetti. Baby clothes: Tane Organics; TaneOrganics.com.

woman with dogs in mini skirt

Photo: William Garrett

Mini Skirt
"You have to be young—under 30—or have great legs to pull off a mini," says Adam. "If neither of those things applies to you but you absolutely must wear one, wear it with tights so you'll feel more comfortable. I may get a lot of flack for this, but I just don't think you should wear a mini if you're over 30."

How to Wear It: Choose skirts that are slightly A-line (not tight), and pair them with flats or wedge boots. Wear looser tops to balance the skirt's skimpiness. And please, don't wear a mini to the office.
If You're Short: Petite women can get away with minis more easily. But they still need to wear tights if over 30.
If You're Tall: Have fun with proportion: Pair with long cardigans and three-quarter-length jackets.
What to Avoid: Blazers ("too Ally McBeal" says Adam). And don't even think about a stiletto unless "trashtastic" is the look you want.

Coat, Jones New York Collection, $299. Skirt, Uniqlo, $30. Scarf, Baby Mo. Tights, No Nonsense. Boots, Pollini by Nicholas Kirkwood. Great Dane provided by the Mid-Atlantic Great Dane Rescue League.

women in pleated skirts having drinks

Photo: William Garrett

Pleated Skirt
This style flatters most body types. "It glides as you walk, leading the eye away from problem areas," says Adam.

How to Wear It: Choose a fabric with an easy drape, like silk crepe, and if you're thicker in the middle, make sure the skirt has a wider waistband. Top with blazers and knits; shoes should be delicate. Think stilettos, pumps with bow details, slingbacks, and T-straps.
If You're Short: Don't go shorter than knee length "unless you want to look like Britney Spears in the 'Baby One More Time' video," says Adam.
If You're Tall: Try a midcalf length for a '20s look.
What to Avoid: Any kind of boot, which will clash with the skirt's ladylike vibe.

Shirt, Tommy Hilfiger, $70. Jacket, Lauren Ralph Lauren, $260. Skirt, Kate Spade New York, $298. Watch, Michael Kors. Tights, DKNY. Shoes, CH Carolina Herrera. Sweater, 525 America, $48. Skirt, Trina Turk, $238. Watch, Movado. Stockings, Assets Red Hot Label by Spanx. Shoes, L.K. Bennett.

Shot at the John Dory Oyster Bar, New York City. These tasty cocktails—the Set Sail (left) and the Queen's Park Swizzle—are the NYC restaurant's signatures.

Next: 7 new fall skirts—plus the perfect shoes to pair them with