First Day of School Outfits That Don't Try Too Hard

First Day of School Outfits That Don't Try Too Hard

Whether you’re a freshman going to college for the very first time or a senior who’s been doing this for a while now, the first day back to school tends to be a little stressful for everyone. Even if you’ve been planning for months, let’s be real: The night before your first day is usually a mess. Since you’re sure to be super busy getting all of your materials ready, setting up lunch dates with your friends, and memorizing your schedule, the last thing you should be stressed about is picking the perfect first day of school outfit.

We know that there’s no better way to kick off the semester right than feeling confident about your look. Keep scrolling for a list of nine killer looks for your major comeback to school.

Summery blue dress

PHOTO: Mackensy Moor, College Fashionista Alum

Combine a Mini Dress with Sneakers For a Sporty-Chic Look

This outfit is the move if you are into sporty-chic looks. While the dress is sophisticated, the sneakers counterbalance that by introducing a sporty vibe. This look is perfect for your first day of school because it combines style with comfort.

Get the look: Zara Pompom Jumpsuit Dress ($16), Superga 2750 Cotu Classic ($65), Zara Basic T-Shirt ($155)

Wear Tailored Track Pants and an Off-the-Shoulder Top the First Day of School

PHOTO: Stella Pyles, Liberty University

Go for Street Style with Track Pants and Sneakers

Check your Instagram and you’ll notice that track pants have been a must-have item in the wardrobes of influencers ATM. The ones chosen here by Community Member Stella aren’t too sporty because they’re cut similar to tailored pants. For the top, wearing a basic off-the-shoulder shirt is a great way to highlight the athleisure-style pants. If you are going for high-waisted pants, a tube top like Stella’s fits perfectly. Vans or any other sneakers of your choice will be your best bet to complement the outfit.

Get the look: Aritzia Conan Pant Terado  ($118), Aritzia Tournesol T-Shirt ($27), Vans Old Skool ($55)

maxi jacket and basics look

PHOTO: Maddy Haller, College Fashionista Alum

Add Statement Outerwear to a Black and White Look

One of the best techniques to get a low-key look for your first day of classes is to highlight one piece of clothing as the focal point of your outfit. In this case, the white basic tee and black skinny jeans combo would be a very simple outfit were it not for the nude longline jacket. It adds more personality to the look and shows the effort you put into it (even if you just grabbed the jacket while leaving home in a hurry).

Get the look: Aritzia Kahlo Jacket ($199), Zara Ribbed T-Shirt ($18), Urban Outfitters BDG Twig High-Rise Skinny Jean  ($58), Via Spiga Peep Toe Mule ($113)

Shirt and denim shorts look

PHOTO: Demi Balogun, Purdue University

Pair a Button-Down With Denim Shorts for a Reliable Classic

Who doesn’t love the practicality of denim shorts? They’re great go-to pieces of clothing for different occasions and look amazing paired up with different tops, especially button-up shirts. Tip: You can wear the shirt French-tucked into the shorts or with a front-knot and with the sleeves rolled up, just like Demi did. This combo seems like a no-brainer, but it’s the perfect first-day-of-school outfit if you’re shooting for a laid-back vibe.

Get the look: American Eagle Tomgirl Midi Shorts ($25), Aritzia Boy Shirt ($35)

Stripped pants look

PHOTO: Julia Marzovilla, Loyola Marymount University

Stay Comfy (And Stylish) With Striped Pants and a Basic Tee

We already know that you can’t go wrong with the famous graphic tee plus basic pants look, right? So why not try giving the reverse a shot? This Community Member chose to combine striped pants with a basic cotton tee and sneakers. The result is a seemingly-basic (and totally comfy) look that will turn heads as you make your way across campus.

Get the look: Brandy Melville Tilden Pants ($35), Madewell Knot Front Tee ($32), Nike Classic Cortez ($70)

floral skirt look

PHOTO: Leila Clairville, London College of Fashion

Combine a Floral Skirt With a Crop Top and Sneakers if You Don’t Want Summer to End

Day one and missing summer already? No judgement—we’ve been there. Incorporate florals into your first-day look and it’ll basically still feel like you’re on vacation. Here, this Community Member chose to mix and match styles by pairing her floral maxi skirt with a crop top and sneakers, obtaining a romantic look with traces of street style.     

Get the look: ASOS Design Mixed Blue Floral Maxi Skirt with Hanky Hem ($44), Aritzia Cathay Tank ($28), Urban Outfitters Venice Oval Sunglasses ($10), Adidas Superstar Foundation Shoes ($80)

dress and denim jacket look

PHOTO: Faith Roda, Philadelphia University

Throw Your Favorite Denim Jacket Over a Fresh Dress on Your Way to an 8 A.M.

Hit snooze a few too many times before your early morning class? This outfit is an easy option if you need to sprint across campus but still want to look stylish. The juxtaposition of the classic dress with the oversize denim jacket and sneakers looks fashion forward but feels like you’re still wearing your pajamas. Now that’s a win-win situation.

Get the look: Urban Outfitters Finnigan Floral Mini Dress ($59), Urban Outfitters Levi’s Oversized Denim Trucker Jacket ($98), All Star Converse Chuck Taylor High Top ($55)

vinyl skirt and oversized graphic tee look

PHOTO: Ellie Kim, Fordham University

Tackle a Vinyl Skirt for an Unexpected Way to Ace Your First Day

You may have seen vinyl pieces of clothing appearing in recent Vogue spreads, but who knew that you can wear them IRL? The key is to combine these shiny statement pieces with more casual basics. The graphic tee and the oversized denim jacket go with every look and tone down the “going-out” vibe of the trendy skirt.  

Get the look: Miss Selfridge Vinyl Mini Skirt ($16), Urban Outfitters Junk Food Mustang Crew-Neck Tee ($39), Urban Outfitters Levi’s Oversized Denim Trucker Jacket ($98)

denim jacket and yellow dress look

PHOTO: Chloe Felopulos, Fordham University

Give Your Favorite Dress a Twist With Fishnets And A Cadet Hat

Who doesn’t have a simple dress and jean jacket in their teeny-tiny dorm room closet? While this match-made-in-heaven combo is already too cute, Community Member Chloe gave it a totally unexpected twist by adding fishnet socks and a cadet hat. With just a few simple accessories, you can update your wardrobe staples into an eye-catching outfit for your first day back to campus.

Get the look: Aritzia Sorrell Dress ($88), American Eagle Boyfriend Fit Denim Jacket ($70), Urban Outfitters Vintage Surplus Cadet Hat ($18), Adidas Superstar Foundation Shoes ($80), Urban Outfitters Out From Under Fishnet Socks ($3)

Now that you have your first-day outfit sorted, click here for more looks to copy the rest of syllabus week.

Opening image by Brooke O’Hair.