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Back-to-school shopping has always been a thing. Whether it’s a first-day fit or Monday-to-Friday survival wardrobe, the classroom has doubled as a runway for over a century. And just like cafeteria food and slang, school style has gone through some phases.

From wartime pinafores to Gossip Girl plaid to TikTok thriftcore, school fashion has always mirrored the times. It reflects what we valued, what we pushed back against, and what trends were simply too good or too cringey to let go.

So grab your hall pass. We’re going on a fashion field trip through the decades to see which trends still pass the vibe check.

Back when “What are you wearing?” was not a question but a rulebook. 

Early 1900s looks were straight out of a period drama with high-neck blouses, pinafores, long skirts, and if you were lucky, a sailor collar for a little extra fun. Boys wore button-ups, knickerbockers, and knee socks. Think Anne of Green Gables without the scenic countryside.

By the 1930s, Peter Pan collars and pleated skirts became the unofficial uniform thanks to department store catalogs and old Hollywood films. When WWII arrived, rationing took over and style went fully practical. Utility dresses, sturdy cardigans, and sensible shoes had to last through both recess and a growth spurt.

Trending Then: Peter Pan collars, saddle shoes, hair bows

Trending Now: Collared blouses layered under sweaters, cardigans, Mary Janes

GAP Puff-Sleeve Collared Top // The A&F Madeline Textural Crew Sweater // Michaela Mary Jane Flat

The 1950s were peak polished. Imagine Grease’s Pink Ladies in cardigan sets or Sandy’s full skirts on the bleachers. Sweater sets, calf-length skirts, and loafers were everywhere.

By the 1960s, the British Invasion brought mod minis, bold prints, and Twiggy-approved shift dresses. Girls found ways to sneak shorter hemlines past the rules, and color suddenly mattered just as much as the cut.

Trending Then: Cardigan sets, shift dresses, headbands

Trending Now: Mod minis, knee socks, vintage plaid skirts, Mary Janes

Free People Misty Net Pointelle Tall Socks In Cream // Edikted Roni Plaid Pleated Mini Skirt // Beverly and Beck Elizabeth Mini Dress

The 1970s classrooms were a disco-meets-folk festival. Bell-bottom jeans, fringe vests, tie-dye tees, and platform shoes ruled the hallways. If you were feeling more preppy, plaid skirts with knee-high socks and blazers gave off “future student council president” energy.

The ‘80s cranked up the volume in every sense with bigger hair, bolder colors, more layers. John Hughes movies became style bibles: pastel polos and pleated skirts for the preppy types (Pretty in Pink), neon windbreakers for the sporty crowd (The Breakfast Club’s Emilio Estevez), and thrifted punk looks for the Molly Ringwalds who wanted to stand out.

Trending Then: Varsity sweaters, acid-wash jeans, scrunchies, high-top sneakers
Trending Now: Bomber jackets, oversized blazers, chunky sneakers

Levi’s Varsity Bomber Jacket // New Balance 9080 Sneakers // Cotton On Oversized Blazer

The 1990s could not decide on a single mood. Some went full Clueless in plaid skirt sets, while others took the My So-Called Life route with flannels, ripped jeans, and Docs.

Then Y2K arrived and subtlety disappeared. Britney’s “…Baby One More Time” inspired tied-up shirts and low-rise skirts. Mall culture put Abercrombie logos on everything. Juicy Couture tracksuits, butterfly clips, bedazzled everything, and mini bags that could barely fit a flip phone became the ultimate accessories.

Trending Then: Baby tees, cargo pants, layered tanks, mini skirts, chunky belts

Trending Now: Clueless plaid, wide-leg jeans, Y2K accessories

Princess Polly Cottesloe Blouse Top // The A&F Low Rise Ultra Loose Jean // Retro Oval Cat Eye Sunglasses

Today’s “trend” is that there is no single trend. It is all about the remix. You might wear a thrifted 90s slip dress one day and coquette bows the next. Gorpcore, balletcore, and vintage varsity jackets can live in the same outfit and no one blinks.

The old rulebook is gone. The only one that matters now is simple. If it makes you feel like the lead in your own teen movie, it works.

Trending Then: There is no “then”

Trending Now: Everything from every decade, styled your way

Levi’s Baggy Dad Jort // Steve Madden Astor Brown Leather Boots // Edikted Jett Asymmetric Top