What to Wear This Back-to-School Season (Now That You're Not the Same Girl You Were Freshman Year)

July 29, 2025

You’ve changed. Maybe it’s your body. Maybe it’s your mindset. Maybe you just don’t feel like the girl who used to live in biker shorts and oversized tees. Now that school’s back in session, your style should reflect who you’ve become.

This isn’t about reinventing yourself overnight. It’s about evolving—quietly, confidently—and having the tools to help you figure out what works for you now.

LookSky is your favorite online clothing store—but smarter. See your picks, try them on, and buy what actually works. Every look is matched to your shape, color season, and vibe.

First-year you had a uniform. Now you're building a wardrobe.

Back then, it was all about grabbing something comfortable and hoping it passed for cute. But now, your style’s shifting. You want to look more intentional—even if you’re still rushing to class. You want clothes that feel good on your body, not the girl next to you. You want to show up—without overthinking it.

That’s where LookSky comes in.

The easiest way to figure out your style right now

When you open the LookSky app, you’re not just getting “what’s trending.” You’re getting a feed of outfit ideas personalized to your body shape, style vibe, and color palette. It’s curated for you today—not the you from 18 months ago.

Just take the quiz, upload a photo, and let LookSky show you what fits, what flatters, and what feels like your next chapter.

Here’s what that evolution can look like

You don’t need to throw out your whole closet. These five outfit formulas blend comfort with grown-girl energy. Think polished but wearable. Effortless but intentional.

Back to School outfit with ribbed tank, oversized shirt, and skort

Ribbed Tank + Oversized Shirt + Skort

Same chill energy, but with a little more structure.

LookSky Picks (all available for purchase on the app)

• Everyday Linen Shirt

• Where it’s from: Free People

• Women's Ribbed Tank Top Knit Square Neck Sleeveless Shirts SUmmer Casual Basic Tanks

• Where it’s from: Amazon

• Breezeful High Waisted Wrapped Pleated 2-in-1 Pocket Adjustable Buckle Mini Quick Dry Casual Skirt

• Where it’s from: Halara

• YPE SculptLUX Lined Asymmetrical Wrap Skort

• Where it’s from: Abercrombie & Fitch

Try it on virtually to check how the proportions feel on your current shape.

Floral mini dress and letterman jacket back to school outfit

A Cute Floral Mini + Letterman Jacket

Cute for those Friday night date nights

LookSky Picks (all looks available for purchase on the app)

• Valencia Dress

• Where it’s from: Reformation

• Eliza Floral Tie-Front Mini Dress

• Where it’s from: PacSun

• Floral Open Back Print Cami Short Dress

• Where it’s from: Commense

• Fernando Jacket

• Where it’s from: Revolve

Use the virtual try-on to test where the hem hits and whether the color works for your skin tone.

Pleated mini skirt and oversized sweatshirt outfit idea

Pleated Skirt + Oversized Sweatshirt

Cozy, but elevated. Cute, but grown.

LookSky Picks (all available for purchase on the app)

• Solid Pleated Denim Mini Skirt

• Where it’s from: Lewkin

• Topshop Denim Box Pleat Mini Skirt in Brown

• Where it’s from: ASOS

• AE NFL Kansas City Chiefs Crew Neck Sweatshirt

• Where it’s from: American Eagle

• Pleated Skort

• Where it’s from: Uniqlo

Try this combo on in-app to balance warmth, shape, and style for your proportions.

Back to school outfit with rugby shirt and denim jeans

Rugby Shirt + Wide-Leg Denim

The most basic upgrade. Still wearable every day.

LookSky Picks (all available for purchase on the app)

• Maurie Polo

• Where it’s from: Revolve

• Magda Low Rise Acide Wash Jeans

• Where it’s from: Pacsun

• Leisure Long Sleeve Top

• Where it’s from: Revolve

• Dome High Rise Wide Leg No Cuff

• Where it’s from: AGOLDE

See the full look on your virtual body before you buy. No regrets, no returns.

Sporty back to school tank top and track pants outfit

Basic Tank + Track Pants

This is your “I woke up like this, but in It-Girl way” look.

LookSky Picks (all available for purhcase on the app)

• Always a Vibe Basic Knit Tank Top

• Where it’s from: Winsor

• Missguided x Playboy Wide Leg Side Stripes Varsity Sweatpants

• Where it’s from: Missguided

• Women's Sleeveless Ribbed Tank Tops Knit Summer Basic Tee Shirts

• Where it’s from: Amazon

• All Star Season Track Pants Navy

• Where it’s from: White Fox

Use virtual try-on to test movement, waist rise, and proportions in real time.

Trying things on is how you evolve—not guess

You don’t need to reinvent your entire vibe. You just need to see what feels good now. That’s where LookSky’s virtual try-on comes in. Instead of buying pieces that worked for you two years ago, or hoping TikTok trends fit your body, you get to preview the full outfit on your actual shape.

You can try a crop top again. A new color. A mini skirt that doesn’t scare you.
It’s about experimenting without commitment—and learning what today-you actually loves.

FAQs

What if I don’t know my style yet?
Perfect. LookSky helps you figure it out. You’ll get personalized outfit ideas based on your shape, style preferences, and color palette.

Is this like a stylist app?
Nope. It’s not someone else’s opinion. It’s smart tech that pulls together outfits that are already tailored to you.

Can I shop in the app?
Yes! One cart, 400+ brands, and free shipping on eligible picks.

From the Founder:

“Style evolves—especially during college. We built LookSky to help you dress for who you are now, not who you used to be. Because growing up doesn’t mean losing your style. It means finding it,” says Samantha Shih, co-founder of LookSky and fashion industry veteran.

Ready to upgrade your back-to-school wardrobe?

Try on new looks, experiment with your vibe, and build a closet that finally feels like you.

[Let’s See What Fits the New Me]

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