The skinny

Melissa shoes: left, $59; middle, $64, both at Akira

A little baby powder and Vaseline can alleviate the rub-your-thighs-dry chafing effect of skinny jeans in the summer, but they don’t do jack when it comes to preventing “peg leg.” We turn to two sartorial aces for advice on how to flatter your legs without tall winter boots.

While Kelly Whitesell, co-owner of Wicker Park boutique Eskell, touts the round-toe flat for an Audrey Hepburn–esque silhouette, she’s all about the wedge (pictured, left) when it comes to a lean, long look. That said, “You don’t want to run around looking like you’re wearing heels all the time…like you’re trying too hard,” says Whitesell, so she suggests the wedge-in-disguise 80%20 (pictured, right). Made by Ce Ce Chin in New York, kicks like this canvas lace-up appear as casual as a run-around-town sneaker but, with a built-in two-and-a-half-inch lift, elongate your legs like a heel. $90 at Eskell (1509 N Milwaukee Ave at Honore St, 773-486-0830, eskell.com).

Whitesell and Levi’s style expert Erica Archambault both are fans of scrunching the edge of the pant, but you also can mix it up with the cuff. Try these two versions: the four- to five-inch ’50s-style cuff above the ankle or a one- to two-inch roll around the ankle.

If you’d rather not roll ’em, the decorative green stitch beneath the fold of these Levi’s organic cotton eco Hi-Rise Skinny Jeans (pictured, middle) break up the bottom of the leg and come in a dark (read: more flattering) finish. “A high-rise jean makes your legs look longer and leaner,” says Archambault, and who would argue with that? $78 at Levi’s.