July 23, 2025 — Charlotte Pennington
  • The best outfit ideas for high school prioritize long-term wearability as much as everyday comfort.
  • Hoodies, sweatshirts, shorts, jeans, and linen separates are dependable pieces you can wear year after year.
  • Cali1850’s Lazy Sunday collection offers chic athleisure essentials that are perfect for school, college, and everything in between.

A high school student who juggles academics, extracurricular activities, and a social life doesn’t really have the time to play dress up every morning. So, they need a wardrobe that keeps things simple and helps them look presentable without any guesswork. This can only be achieved through a good mix of tried-and-true staples that fit into cohesive looks. 

Athleisure wear is the best aesthetic to lean into for back-to-school high school outfits, thanks to its comfort and versatility that extends way beyond the classroom. However, we have a little more variety here to help you build a well-rounded wardrobe that will support you through your busiest academic years. 

1. A Cozy Sweat Set

A girl in black sweatpants and a matching hoodie

Cozy hoodies with a baggy fit are universally flattering. Pair one with equally loose-fitting sweatpants, and you have every high schooler’s comfort outfit for back-to-school season! Try lighter tops with darker bottoms to create contrast. Or, grab a matching sweat set for a coordinated look that requires minimal effort. Finish with any sneakers that complement the hoodie.

2. An Embroidered Sweatshirt and Shorts Set

A girl in a white embroidered sweatshirt & sweat shorts

Fleece sweatshirts are incredibly comfortable. It’s a fact. But the experience is on a whole other level with Lazy Sunday’s women’s embroidered sweatshirts and Cali1850’s cloud fleece shorts. These chic pieces offer warmth and softness like no other. They’re consciously designed to keep up with active lifestyles, so they’ll be in your line-up of high school outfit ideas until you decide to retire them. 

If you want to invest in only one set, stick to neutral colors so you can pair them with other tops and bottoms with ease. 

3. A Cropped Top and Flared Jeans

Two women in cropped tops & flared jeans

The idea of wearing sweats to school every day is tempting, but you’ll likely get over it as the year progresses. Keep a sharper look ready in your rotation with a pair of women’s flare jeans that go with all your comfy sweatshirts, sweaters, and T-shirts. 

Cargo-style jeans in a medium or light wash make any outfit more interesting, whether it’s paired with a cropped hoodie, oversized graphic tee, or button-down shirt. This is the perfect back-to-school outfit for style-conscious high school students.

4. A Striped Sweatshirt With a Skirt to Match

A girl in a sporty white sweatshirt & black skirt

Diversify your school wardrobe further by adding a skirt to the mix. Pick something sporty you can wear with a nice polo, cropped T-shirt, striped sweatshirt, and sneakers. A pleated tennis skirt is a stunner that brings a preppy vibe to any look, but an A-line style with subtle elevating details like a wraparound design or contrast stitching works just as well for an understated feel. For a more feminine high school outfit, try this idea with a ruffled skirt or a linen maxi skirt instead.

5. Airy Linen Separates That Pair With Everything

A girl in a white linen shirt & olive linen pants

Linen pieces deserve a place in every high schooler’s back-to-school outfit lineup simply for their breezy aesthetic. But they score full marks on comfort too! Grab a few linen button-down shirts and pull-on linen beach pants in soft, earthy colors to wear together or with other pieces in your wardrobe. These lightweight pieces will keep you cool through the heat of late summer and transition well into fall with the right layering.

Need more elevated basics for back-to-school outfits? Explore our best-selling women’s leisure wear to discover more high-quality pieces that keep you comfortable and styled from the classroom to the gym and beyond. Plus, get free same-day USA shipping on every order!

Author Bio

With a strong belief in using fashion as a means for self-expression, Charlotte Pennington helps individuals embrace their unique personal style and showcase it through their clothing choices. From her early days flipping through fashion magazines to her adventures scouring thrift shops for hidden gems, fashion has always been her muse. Shaped by California’s iconic and relaxed fashion influences and armed with a pen and a keen eye for trends, Charlotte now shares her love for fashion through her writing.