Back in the 1960s, fashion was fearless. We didn’t just follow trends—we wore them, owned them, and strutted around like they made perfect sense (even when they didn’t). From daring hemlines to dizzying prints, the ’60s gave us a lot to remember—and a few things we’d maybe rather forget. Still, deep down, there’s something charming about those old outfits that makes us smile… even if we wouldn’t be caught dead in them today.
1. Go-Go Boots with Everything
Oh, those white vinyl go-go boots. We wore them with mini skirts, shift dresses, and sometimes even things they really had no business going with. They were bold, shiny, and made you feel ten feet tall—even if they squeaked with every step. Cool Old Stuff marches down memory lane to explore the history of these boots and their own impact on fashion history around them.
Sure, they weren’t always the most comfortable choice, especially in warmer weather. But they were the symbol of swinging ’60s fashion, and everyone from mod teens to middle-aged trendsetters gave them a whirl. Looking back, we might cringe a little, but we also remember how fun they made us feel.
2. Psychedelic Prints That Could Cause Whiplash
If your outfit didn’t make people squint, was it even worth wearing? Psychedelic patterns in every swirling, eye-popping color imaginable took over blouses, dresses, and even men’s shirts. The louder, the better—and bonus points if it clashed with your pants. PRINT Magazine traces the rise of this trend and the implications of why it became so popular when it did.
These prints were bold statements of rebellion and individuality. We were embracing freedom, and fashion followed suit. Today, they might make us dizzy, but back then, they were groovy as can be.
3. Bell-Bottoms That Could Sweep the Street
Bell-bottoms were more than a cut of pants—they were a lifestyle. Tight at the top, flared dramatically at the bottom, and always paired with a little swagger, they made you feel cool, even if they dragged in puddles. Shaft Jeans also points out the role of these particular pants as a bold, stylish symbol of youthfulness and rebellion.
We wore them in denim, corduroy, and wild prints that could knock your socks off. Sure, they weren’t the most practical choice, especially in a surprise rainstorm. But the flare gave every step a bit of flair, and who didn’t love that?
4. The Beehive Hairdo
Achieving a beehive wasn’t for the faint of heart—it took teasing, hairspray, and at least one afternoon to get it right. The taller the better, and bonus points if it held through an entire night of dancing.
We laugh now thinking about the hairspray clouds and aching arms. But there was something magical about getting it just right and watching it hold like a sculpture. It was a crown, and we wore it proudly.
5. Nehru Jackets for the Cool Crowd
If you wanted to look worldly and just a little mysterious, the Nehru jacket was your go-to. With its collarless design and sleek silhouette, it said you were in tune with the global groove.
It popped up everywhere—from musicians on album covers to young men trying to stand out at school dances. Looking back, it feels a bit like a costume, but it sure had style in its moment. Regret it? Maybe. Miss it? Just a little.
6. Mini Skirts That Barely Passed the Dress Code
When the hemlines rose, so did eyebrows—and parents everywhere held their breath. Mini skirts were the fashion rebellion of the decade, and we wore them proudly, even if we had to tug them down every five minutes.
They came in bold colors, geometric patterns, and sometimes matched our go-go boots perfectly. Teachers didn’t always approve, but we felt modern and free. Today’s versions may be tamer, but the original minis were something else.
7. Matching Pantsuits for Women
Nothing said confidence like a brightly colored pantsuit with matching jacket and slacks. It was professional, playful, and unapologetically bold—especially when paired with a coordinating turtleneck.
We strutted into offices, parties, and PTA meetings like we meant business and had style. Sure, the cuts were boxy and the polyester less than forgiving, but they were empowering in a way that still sticks with us. Regrettable? A bit. Missed? Absolutely.
8. Tie-Dye Everything
Tie-dye wasn’t just a look—it was a philosophy. We twisted, dyed, and created our own wild masterpieces on shirts, dresses, and sometimes even undergarments. It was colorful, chaotic, and totally unique.
It also bled in the wash and never quite matched anything else you owned. But it stood for peace, love, and individuality—and that kind of fashion spirit never really goes out of style. Even now, we smile when we see it.
9. Wide Collars That Took Flight
Whether on a button-down shirt or a dress, collars in the ’60s didn’t sit quietly—they made a statement. They flared, pointed, and sometimes reached halfway down your chest.
Men rocked them with gold chains and blazers, while women paired them with pinafores and pastel sweaters. They made every outfit just a bit more dramatic. Subtle? Not a chance. Memorable? Definitely.
10. Patterned Tights in Bright Colors
Plain nylons just weren’t enough during the mod era. We slipped into fishnets, stripes, and colorful tights that turned our legs into works of art. Sometimes they matched our outfits… and sometimes they didn’t.
They ran easily and weren’t always comfortable, but we loved the way they transformed a simple dress. It was fun, expressive, and just plain different from anything that came before. We don’t miss the snags—but we do miss the whimsy.
11. Bold False Eyelashes
Eyelashes in the ’60s weren’t about subtle enhancement—they were about drama. We glued on big, bold lashes that looked more like feathers than makeup, inspired by the likes of Twiggy and Dusty Springfield.
They fluttered when we blinked and made everything feel a bit more glamorous. Sometimes they came unglued mid-party, but that was half the fun. They weren’t easy to pull off, but when it worked, it really worked.
12. Men’s Ruffled Dress Shirts
For formal occasions, a plain white shirt just didn’t cut it. Men wore ruffled fronts, pastel colors, and even velvet trims to stand out on the dance floor—or at prom.
It was flashy, a little romantic, and a lot of look. Some of those prom photos might make us blush now, but at the time, it felt daring and new. Regrets? Plenty. But also a weird kind of pride.
13. Matching Mom-and-Daughter Outfits
Catalogs loved showing off mother-daughter duos in identical outfits—usually floral dresses or bold pantsuits. We might have groaned about it back then, especially if photos were involved, but secretly, it felt kind of special.
It was a sign of unity, a moment of bonding that sometimes even crossed generations. As awkward as it could be, we still remember the matching dresses and side-by-side hairdos. Would we do it again? Maybe not… but we sure remember it fondly.
The 1960s were a bold time in fashion—full of choices that didn’t always age well but carried real spirit. We took risks, had fun, and wore what made us feel alive, even if it earned some head-shaking in hindsight. Today’s wardrobes may be sleeker, but they don’t always have the same sense of adventure. And sometimes, all it takes is an old photo to make us wish we could try just one of those outfits on again—if only for a moment.
