In Milan, No Pants—No Problem

This color-coordinated outfit turns hot pants into an unexpectedly demure choice. The addition of black tights and a long trench offer some coverage to contrast with the shorts’ micro size.

A pair of oversize tailored shorts powers a playful twist on office dressing.

Let a pair of small shorts peek out from below a coordinated top. The look is streamlined without feeling too matchy-matchy.

In this season-bending outfit, white shorts are styled with wintry staples like a fuzzy coat and turtleneck. The final effect is cozy and polished, and it’s refreshingly easy to re-create.

Skip the traditional suit set for this heat-friendly combination. A pair of long shorts can work for creative offices or dressy occasions when you’re feeling more playful.

Life is easy when getting dressed is as simple as throwing on one great piece and running out the door. A tailored romper can be worn solo, or styled with tops or jackets for some additional color and texture play.

You may be most inclined to style shorts with seasonal footwear like sandals or sneakers. Instead, break out the extra-tall boots for a surprising foil to a pair of tiny shorts.

Try mixing and matching an outfit with a coordinated palette for a fresh ensemble that’s elegant and yet a bit more interesting than wearing a fully matching suit set.

Sweater shorts may seem like a style you’re inclined to wear solely at home on the couch, but go bold and leave home behind. A coordinated knit set is a look that is ideal for transitional weather.

Black on black is a look you can never go wrong with. In fact, this ensemble would work just as easily for lunch with friends as it would for a formal event when you want to swap out your usual party dress.