How to Style Shorts for Every Occasion This Summer

Photo Credit: Madison Milliken

If you’ve ever stood in front of your closet and thought, “I want to wear shorts… but I don’t know what kind of top, shoes, or vibe I’m going for,” — same.

Styling shorts is supposed to be easy, but somehow it turns into a game of “does this look like I just rolled out of bed or does this actually work?” Shorts can feel too casual, too fitted, or just…off, depending on the occasion.

But once you know how to balance the vibe, they become your most underrated summer staple.

Here’s how to style shorts for every summer occasion—from coffee runs to date nights—and look instantly put-together.

1. For Casual Days When You Just Want to Be Comfortable (But Not Sloppy)

If you’re looking for a casual summer shorts outfit that doesn’t scream “pajamas,” this is the formula. Soft fabrics, neutral tones, and just enough polish to feel like you tried.

H&M

Ribbed Tank Top

$12.99

H&M

Airy Drawstring Shorts

$29.99

Amazon

Slip-Resistant Slides

$49.90

2. For a Summer Brunch Where You Want to Look Cute (But Not Overdressed)

This summer outfit with tailored shorts hits the sweet spot between effort and ease. Structured but not stiff—and cute enough for mimosas.

Amazon

Basic Bodysuit Tank Tops

$24.97

Amazon

Wide Leg Tailored Shorts

$24.99

Amazon

Leather Slides with Square Open Toe

$22.99

3. For the “I’m Just Running Errands But I Want to Feel Styled” Day

This is your go-to athleisure shorts outfit for summer. Comfy enough for Target runs, but still cute enough to post on IG stories.

Amazon

Drop Shoulder Casual Short Sleeve Tee

$24.99

Amazon

Beach Bottoms

$14.99

Adidas

Gazelle Indoor Sneaker

$120

4. For Outdoor Events Where You Want to Look Put Together but Stay Cool

If you’ve been wondering how to style Bermuda shorts without feeling like a substitute teacher, this is it. Balance the longer length with something sleeveless or fitted up top.

Nordstrom

Sleeveless Cotton Blend Crewneck T-Shirt

$25.00

Linden High Waist Denim Bermuda Shorts

$148.00

AllSaints

$199

Sian Raffia Two-Strap Sandal

5. For a Laid-Back Summer Date Night

This date night shorts outfit feels elevated without trying too hard. Bonus: faux leather or satin always makes things look more intentional.

Good American

Super Stretch Deep V-Neck Bodysuit

$69.00

Good American

Suiting Longer Length Shorts

$149.00

Nordstrom

Jamie Block Heel Sandal

$59.95

6. For Travel Days or Summer Road Trips

What to wear with linen shorts? Start here. This outfit is breezy, easy to layer, and perfect for long hours in the car or airport.

Franne Golde

Crisp Cotton Button-Up Shirt

$148

ASTR the Label

Asymmetric Pleat Shorts

$75.00

Zella

Go-To Rib Performance Tank

$39.00

Free People

Blossom Buckle Flat Sandal

$138.00

7. For the “I Want to Be in Shorts but Still Look Elevated” Moment

If you’re tired of the same old shorts-and-tee look, a co-ord set is your summer glow-up. One of my favorite shorts outfit ideas for summer 2025—you look styled without overthinking anything.

Petal & Pup

Flynn Cotton Tie Front Top & Drawstring Shorts Set

$89.00

Söfft

Nadia Slingback Sandal

$124.95