Preppy Spirit Week Outfits

Spirit Week used to stress me out. I liked the idea of it — the themes, the silliness, the excuse to wear something ridiculous on a Tuesday. Most days, I wasn’t in the mood to go all out. I just wanted something that felt playful but still… me.

So I’d grab the closest thing in my closet that sort of matched the theme — a striped pajama set on pajama day, a navy blazer for decade day, a ribbon in my hair for twin day and hope for the best.

This isn’t a guide to winning “most spirited.” It’s for anyone who likes to quietly play along — the girls who prefer loafers to tutus, and outfits that work just as well in math class as they do on theme day.

Pajama Day → The Cozy Prep

This one’s tempting. It’s 7:12 a.m., you’re tired, and technically, you could just roll in wearing what you slept in. But if you want to feel a little more put together (without trying too hard), here’s the move:

Go for a matching pajama set. Something with buttons and piping — maybe navy or striped or even a soft floral if you’re feeling sweet. Toss a crewneck or cardigan over your shoulders, slip on your go-to sneakers or flats, and you’re basically winning at cozy-but-cute. Still feels like pajamas, but in the “I’m trying a little” kind of way.

Twin Day → Just Pick a Uniform

This one’s fun if you plan ahead — or a little chaotic if you forget and end up whispering “wanna match?” to someone during homeroom. Either way, you don’t need anything dramatic.

Just wear something simple you both already own — like white button-ups and jeans, or a cardigan with sneakers. You don’t need to be twins-twins. If your outfits look like you maybe planned it on the walk to class, it counts.

Decade Day → A Hint, Not a Costume

The key here is to nod to the decade, not turn into a character from a theme party. You don’t need to dress like a movie extra — just borrow one or two pieces that give the idea.

A slouchy blazer and gold hoops can say ‘80s. You could wear a sweater vest and loafers and call it ‘90s. Or grab a midi skirt and a tee and say it’s ‘70s — no one’s going to fact-check you. Just pick something with the right vibe and don’t overthink it.

If it helps, think of someone from that era who actually had good style — not the exaggerated version. You’re not going to a costume contest. You’re just showing you got the memo, quietly.

Character Day → Just Steal Their Style

If the theme is to dress like a character, you don’t have to show up in a wig or carry a fake wand around. Just pick someone whose style you already kind of love, and wear something they might wear — not a full costume, just the vibe.

Rory Gilmore? Easy. Skirt, knit top, book in hand. Matilda? A pinafore and a bow. Even something as simple as a trench coat and ballet flats could pass as Audrey Hepburn if you squint.

It’s less “look who I’m dressed as” and more “I stole her closet for the day.” Subtle always wins.

Wacky Wednesday → But Not Actually Wacky

This one’s always a little weird. Some people go full chaos — shirts backwards, five hats, socks on their arms. But you can keep it simple and still join in.

Try wearing things you wouldn’t normally put together, but that still kind of work. Like a striped top with a plaid skirt. Or layering something preppy in a slightly off way — like a vest over a hoodie or two collars poking out.

It doesn’t need to be loud. Just a little offbeat is enough.

Anything But a Backpack Day → Quietly Ridiculous

This one always makes me laugh — people lugging their books in laundry baskets, toy carts, even a cereal box once. Total chaos, in the best way. It’s chaotic in the best way — but if you’re not into hauling a trash can around all day, there are still options.

Try something that’s funny, but kind of cute too. A vintage picnic basket. A tote bag from your mom’s closet. A little rolling suitcase. Even a giant handbag that barely fits your books — it counts.

The goal isn’t to be the most ridiculous. Just… not a backpack.

School Colors Day → Just Add One Thing

This one’s pretty chill. You don’t need to drape yourself in head-to-toe spirit gear or pull out face paint.

Just wear one thing in a school color — a sweater, a ribbon, maybe socks. If you already have something in your closet that works, great. If not, borrow. That’s half the fun anyway.

No need to go big. One little thing is enough to show you’re in it.

Final Thoughts

You don’t need a costume closet to enjoy Spirit Week. Just a few pieces you already love, a little creativity, and maybe a friend to match outfits with.

It’s not about being the most extra — it’s just about having a little fun and still feeling like yourself while you do it.

About the Author

Picture of Marija

Marija

Marija shares a slower approach to style from her home in Italy — one built on quality, quiet confidence, and a love for what lasts.

Leave a comment

SIMILAR POSTS

Join the Heritage Mode Maison Community – Timeless Fashion, Curated for You.