Casual and dressy outfit with khakis

Photo: Devon Jarvis/Studio D

The Khaki
Go one size larger than usual. Khakis should fit like boyfriend jeans—not too pressed or tight. A sparkly heel and layered, embellished top complete the high-low mix.

Jacket, $1,195; Gryphon, 212-764-3059. Top, $178; BCBG. Khakis, $50; Gap.
Casual and dressy outfit with flats

Photo: Devon Jarvis/Studio D

The Flat
There is nothing more modern than wearing flats with a cocktail dress. It's a very self-assured look, so go for it! Tan accessories balance the formality of the dress.

Dress, $485; Lotusgrace. Belt, Lands' End. Bag, Raoul. Bracelet, Bougainvillea. Shoes, Tory Burch.
Casual and dressy outfit with sweatshirt

Photo: Devon Jarvis/Studio D

The Sweatshirt
Wear it the same way you would a T-shirt. Because a sweatshirt has more volume, a fitted bottom (like this patterned pencil skirt) is best.

Top, $20; Uniqlo. Skirt, $39; Joe Fresh.

Next: Your ultimate guide to spring denim