Sporty Glam

Proportion is key You won’t get the relaxed vibe you’re after with all body-con or all oversized silhouettes. See how Oscar de la Renta balanced his runway looks with a prim fit-and-flare skirt and a body-skimming baseball t-shirt? The proportions play off each other to give it some ease. Do the same with a fitted t-shirt and girlie flared skirt or a slouchy knit and curve-hugging pencil skirt.

Don’t fear contrasting footwear. We’re looking right to Jenna Lyons, who finished a pair of slouchy camo pants with a polished pair of pointed-toe pumps. Yes, each piece hails from a different aesthetic, but together they make the look. It’s easy to replicate with baggy, boyfriend-style jeans rolled up to reveal your favorite heels.