When warm weather rolls around, one of my favorite things to wear is a dressy shorts outfit. Elevated shorts are an unexpected take on a summer evening look, and I’ve found them to be cooler (and more comfortable) than dresses and skirts.
If you’re looking for more ways to wear dressy shorts, keep scrolling for outfit ideas I put together for everything from date night to girls night out, a special dinner on vacation, or (for some of the looks) casual work environments.
Dressy Shorts Outfits
What Types of Shorts Can Be Dressed Up?
With the right styling, I think you can create dressy shorts outfits with just about any pair. Maybe the only exception is cutoffs and biker shorts, but tailored denim shorts will work—I’ve been loving this twill pair!
The job always feels a little easier when I start with shorts that look dressier. The main things that differentiate my dressy shorts from my casual pairs are the fabrication and cut.
Look for details like pleats, buckles, and longer silhouettes (not necessarily bermuda but past mid thigh). If possible, I recommend making sure your dressy shorts are high waisted—this makes it easier to tuck in a flowy blouse or to layer them on top of a fitted tank top/bodysuit.
You can also have fun playing with the layering (add a blazer to any of the looks above to make them more friendly for indoors and into fall!). Colorful short suits are trendy right now and I’ve seen a few affordable options at places like MANGO and Banana Republic—could be a fun combo to try!