woman in midi skirt with baby

Photo: William Garrett

6 of 8
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.