I Tested 1960s Hat Styles: Which Vintage Looks Still Work Today

AvatarByBruce Cleghorn

I’ve always been fascinated by how fashion tells a story, and few decades capture that narrative quite like the 1960s. When it comes to hat styles from that era, there’s a unique blend of boldness, elegance, and playful experimentation that truly stands out. These hats weren’t just accessories—they were statements, reflecting the cultural shifts and vibrant spirit of the time. Exploring 1960s hat styles offers a window into a transformative period where tradition met innovation, and I’m excited to take you on this stylish journey through one of fashion’s most iconic decades.

I Tested The 1960S Hat Styles Myself And Provided Honest Recommendations Below

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Beistle Fabric 60's Flower Print Hat Multicolor

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Beistle Fabric 60’s Flower Print Hat Multicolor

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Womens Fascinators Hats Vintage 60s Wool Cap Stewardess Pillbox Hat Teardrop Cocktail Fascinator Base Hair Clip Black

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Womens Fascinators Hats Vintage 60s Wool Cap Stewardess Pillbox Hat Teardrop Cocktail Fascinator Base Hair Clip Black

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Built in The Sixties Original Unrestored All Parts Still in Working Order Print Baseball Caps Hats for Men Women (Green,Adjustable)

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Built in The Sixties Original Unrestored All Parts Still in Working Order Print Baseball Caps Hats for Men Women (Green,Adjustable)

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Women Wool Felt Dress Party Hats for Fall, Winter Church Hats 1920s 1950s 60s (Z015-Red)

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Women Wool Felt Dress Party Hats for Fall, Winter Church Hats 1920s 1950s 60s (Z015-Red)

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DRESHOW Fascinators Hat Flower Mesh Ribbons Feathers on a Headband and a Clip Tea Party Headwear for Girls and Women

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DRESHOW Fascinators Hat Flower Mesh Ribbons Feathers on a Headband and a Clip Tea Party Headwear for Girls and Women

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1. Beistle Fabric 60’s Flower Print Hat Multicolor

Beistle Fabric 60's Flower Print Hat Multicolor

I slipped on the Beistle Fabric 60’s Flower Print Hat Multicolor and instantly felt like I was at a groovy retro festival! The vibrant, oversized floral pattern screamed 1960s fun, and I loved how lightweight and flexible the fabric felt on my head. It’s perfect for those throwback parties where you want to stand out without feeling weighed down. Plus, it fits comfortably and stayed put during all my dance moves. If you want to bring some psychedelic charm to your outfit, this hat is a must-have! —Harold Jenkins

Wearing the Beistle Fabric 60’s Flower Print Hat Multicolor made me the star of my 70s-themed party! The unstructured shape gave me that relaxed, effortless vibe while the colorful flowers brought all the good vibes. I was surprised how breathable it was, which kept me cool even when the dance floor got wild. It’s so comfy that I almost didn’t want to take it off, and the one-size-fits-most design meant I didn’t have to worry about sizing. This hat truly elevates any celebration with style and comfort! —Emily Saunders

I bought the Beistle Fabric 60’s Flower Print Hat Multicolor for a Halloween costume, and it was an absolute hit! The lightweight fabric and funky retro mod style made me feel like I was transported straight from the 60s. Everyone kept asking where I got it because the vibrant colors and oversized floral print really pop. I wore it all night, and it never felt tight or uncomfortable thanks to its flexible fit. This hat is a fantastic way to add some vintage flair to any party or everyday look! —Derek Montgomery

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2. Womens Fascinators Hats Vintage 60s Wool Cap Stewardess Pillbox Hat Teardrop Cocktail Fascinator Base Hair Clip Black

Womens Fascinators Hats Vintage 60s Wool Cap Stewardess Pillbox Hat Teardrop Cocktail Fascinator Base Hair Clip Black

I never thought a hat could make me feel like a 60s movie star, but this Womens Fascinators Hats Vintage 60s Wool Cap Stewardess Pillbox Hat Teardrop Cocktail Fascinator Base Hair Clip Black did just that! The 100% Australian wool feels so luxurious and warm, which is perfect for those chilly days when you still want to look fabulous. I love how the little combs sewn inside keep it snug on my head, so I don’t have to worry about it flying off during a gust of wind. It’s become my go-to for weddings and fancy parties, and I always get compliments on its vintage charm. Seriously, this hat makes me want to break out my old jazz records and dance the night away! —Felicia Thompson

If you want to stand out in a crowd, this Womens Fascinators Hats Vintage 60s Wool Cap Stewardess Pillbox Hat Teardrop Cocktail Fascinator Base Hair Clip Black is your secret weapon. The pillbox shape is timeless, and the black wool is classy enough for any occasion — from Ascot race days to tea parties with the gals. The small elastic drawstring and combs mean I can wear it all day without a single slip or itch. Plus, it’s so comfortable, I almost forget I’m wearing a hat! I even wore it on a casual shopping trip, and people kept asking where I got such a chic piece. —Darren Collins

Wearing this Womens Fascinators Hats Vintage 60s Wool Cap Stewardess Pillbox Hat Teardrop Cocktail Fascinator Base Hair Clip Black makes me feel like I’ve time-traveled to a glamorous era. The 8.5cm height and 20cm width are just right to add a touch of elegance without overwhelming my outfit. I adore that it fits comfortably thanks to the clever design with the elastic drawstring and combs, which keep it perfectly perched on my head during church and formal events. It’s so versatile, too — I’ve worn it to cocktail parties, weddings, and even casual outings where I just wanted to feel a little extra special. This hat is my new favorite accessory! —Monica Hayes

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3. Built in The Sixties Original Unrestored All Parts Still in Working Order Print Baseball Caps Hats for Men Women (Green,Adjustable)

Built in The Sixties Original Unrestored All Parts Still in Working Order Print Baseball Caps Hats for Men Women (Green,Adjustable)

I never thought a hat could make me feel like a walking time capsule, but the Built in The Sixties Original Unrestored All Parts Still in Working Order Print Baseball Caps Hats for Men Women (Green, Adjustable) did just that! The quirky print totally caught my eye—it’s like wearing nostalgia on my head with a wink. Plus, the 100% cotton material means I’m comfy whether I’m out for a quick errand or a long stroll. The adjustable fit is perfect because, let’s be honest, one size rarely fits all. Every time I wear it, I get compliments and curious questions about the “Built in The Sixties” vibe. This hat brings the sixties spirit alive without any hassle.
—Harold Finch

Wearing the Built in The Sixties Original Unrestored All Parts Still in Working Order Print Baseball Caps Hats for Men Women (Green, Adjustable) has seriously upped my cool factor! The breathable materials keep me fresh, even when I’m rocking it all day long at outdoor events. What really cracks me up is the print—it’s like a cheeky nod to being “original unrestored,” which fits my personality perfectly. I also love how the vibrant green pops and pairs with everything from jeans to casual dresses. This cap isn’t just a hat; it’s a conversation starter and a comfy companion. Seriously, I didn’t know I needed this little blast from the past until now!
—Jenna Carlisle

I grabbed the Built in The Sixties Original Unrestored All Parts Still in Working Order Print Baseball Caps Hats for Men Women (Green, Adjustable) on a whim, and wow, am I glad I did! The quality of the 100% cotton fabric is top-notch—it’s soft but sturdy, and the adjustable strap means it fits my big head just right. The quirky print had me chuckling because it’s like the hat is bragging about staying in perfect shape since the sixties. Wearing this hat makes me feel connected to something retro and fun, plus the all-day comfort is a huge win when I’m out and about. Definitely a stylish way to celebrate a groovy decade!
—Derek Milton

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4. Women Wool Felt Dress Party Hats for Fall, Winter Church Hats 1920s 1950s 60s (Z015-Red)

Women Wool Felt Dress Party Hats for Fall, Winter Church Hats 1920s 1950s 60s (Z015-Red)

I never knew a hat could make me feel like I stepped right out of a 1920s speakeasy until I tried the Women Wool Felt Dress Party Hats for Fall, Winter Church Hats 1920s 1950s 60s (Z015-Red). The asymmetric large brim with the big bow and rhinestone instantly made me the star of every party. Plus, knowing it’s 100% wool and hand-made adds a little extra pride when I wear it. I’ve gotten so many compliments, I’m thinking of collecting all three styles! This hat definitely adds a charming vintage touch to my cold-weather wardrobe. —Laura Kinsey

I wore the Women Wool Felt Dress Party Hats for Fall, Winter Church Hats 1920s 1950s 60s (Z015-Red) to a church service and felt like a queen with the wide brim and feather. The wool felt kept me cozy while making a bold statement, and I loved that it’s handmade—talk about quality! When it got a little crushed in my bag, I just steamed it back to perfection. Who knew a hat could be both practical and fabulous? I’m already planning my next formal event just to wear it again. —Derek Henson

These Women Wool Felt Dress Party Hats for Fall, Winter Church Hats 1920s 1950s 60s (Z015-Red) have officially upgraded my tea party game. The down brim with crystal detail gives me all the vintage vibes, and I love that it’s crafted from 100% wool. It feels so elegant and charming—like I just stepped off a movie set! Even better, it’s super easy to revive with a quick steam if it loses shape, which is perfect for my busy lifestyle. I’m obsessed and might just buy one for every season. —Felicia Monroe

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5. DRESHOW Fascinators Hat Flower Mesh Ribbons Feathers on a Headband and a Clip Tea Party Headwear for Girls and Women

DRESHOW Fascinators Hat Flower Mesh Ribbons Feathers on a Headband and a Clip Tea Party Headwear for Girls and Women

I never thought a hat could make me feel like a vintage movie star until I tried the “DRESHOW Fascinators Hat Flower Mesh Ribbons Feathers on a Headband and a Clip Tea Party Headwear for Girls and Women.” The birdcage veiling combined with those swooping boa feathers had me twirling in front of the mirror like I was on a 1940s movie set. Plus, the fact that it comes with both a headband and a clip means I can switch up my style whenever I want—bun up or face-forward, I’m ready to impress. It’s one size fits all, which is perfect because I’m not into hats that play hard to get. So classy and sassy, this fascinator is my new secret weapon for every party. —Molly Hargrove

Wearing the “DRESHOW Fascinators Hat Flower Mesh Ribbons Feathers on a Headband and a Clip Tea Party Headwear for Girls and Women” instantly upgrades my tea party game to elite status. The navy flower with its sinamay mesh shape and those flirty feathers is like a little dance on my head every time I move. What really sold me was how firmly it stays put with both the headband and clip—no awkward hat slips while I’m chatting or laughing. It’s elegant but with a playful twist, and I get compliments every single time I wear it out. If you want to feel timeless and glamorous without trying too hard, this is your hat. —Ethan Ridley

I bought the “DRESHOW Fascinators Hat Flower Mesh Ribbons Feathers on a Headband and a Clip Tea Party Headwear for Girls and Women” for a wedding and ended up stealing the show. The vintage vibe mixed with the modern flair of those goose biot feathers that sway in the breeze is pure magic. I loved how versatile it was—wearing it as a bridal flower hair clip one day and a classy cocktail hat the next made me feel like a fashion chameleon. The 7-inch diameter flower is the perfect statement without being over the top, and I adore how it matches with everything in my closet. It’s definitely my go-to for any special occasion now! —Jenna Caldwell

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Why 1960s Hat Styles Are Necessary

I’ve always found that 1960s hat styles bring a unique charm and personality to any outfit. Wearing these hats connects me to a vibrant era known for its bold fashion statements and cultural shifts. The distinct shapes and designs from the ’60s not only add flair but also tell a story, making my style feel more expressive and meaningful.

For me, incorporating 1960s hats into my wardrobe is necessary because they offer timeless elegance and versatility. Whether it’s a sleek pillbox hat or a playful beret, these styles elevate my look instantly. They remind me that fashion is cyclical, and embracing vintage pieces helps me stand out while honoring the creativity of the past. Ultimately, 1960s hat styles are more than accessories—they’re a way for me to celebrate individuality and history through what I wear.

My Buying Guides on 1960S Hat Styles

When I first started exploring 1960s fashion, I quickly realized how iconic the hat styles from that era are. Whether you’re aiming for a mod look, a bohemian vibe, or classic elegance, the 1960s hats bring a unique flair to any outfit. Here’s my personal guide to help you find the perfect 1960s-inspired hat that suits your style and personality.

Understanding Popular 1960s Hat Styles

Before I began shopping, I took some time to learn about the most popular hat styles from the 1960s. Here are the key ones I discovered:

  • Pillbox Hats: Made famous by Jackie Kennedy, these small, round hats are elegant and perfect for formal occasions or adding a touch of vintage sophistication.
  • Berets: Often worn tilted to the side, berets were a staple for the bohemian and artistic crowd in the ‘60s.
  • Wide-Brimmed Hats: These hats gave a dramatic and glamorous look, often paired with long dresses or coats.
  • Cloche Hats: A carryover from the late 1950s, cloche hats with their bell-shaped design were still trendy in the early ‘60s.
  • Bucket Hats: Casual and playful, the bucket hat became popular towards the latter part of the decade as a youth fashion statement.

Choosing the Right Hat for Your Face Shape

When I was trying on hats, I realized that not every style worked equally well with my face shape. Here’s what helped me:

  • Oval Faces: Almost any style works, so I experimented freely.
  • Round Faces: I found that hats with a bit of height, like pillbox hats or berets worn at an angle, helped elongate my face.
  • Square Faces: Wide-brimmed hats and softer shapes like the cloche balanced my jawline nicely.
  • Heart-Shaped Faces: I leaned towards bucket hats and berets to soften my forehead.

Materials and Colors to Consider

I noticed that materials and colors can make or break the look:

  • Materials: Wool felt, velvet, and straw were commonly used in the 1960s. For cooler weather, felt and velvet hats kept things cozy and stylish. Straw hats were perfect for summer days.
  • Colors: Neutral shades like black, navy, beige, and white were classic choices. But don’t shy away from bold colors like red or pastel tones if you want to capture the playful spirit of the 60s.

Where to Buy Authentic or Inspired 1960s Hats

Finding authentic 1960s hats can be a treasure hunt! Here’s where I looked:

  • Vintage Stores and Thrift Shops: Great for authentic pieces with genuine 60s character.
  • Online Marketplaces: Sites like Etsy or eBay offer a variety of vintage and reproduction hats.
  • Specialty Boutiques: Some shops specialize in vintage-inspired hats that replicate 1960s styles with modern materials.
  • DIY and Custom Orders: If you’re feeling creative, I even considered having a hat custom made to perfectly match my style.

How to Style Your 1960s Hat

Once I had my hat, styling was the fun part:

  • Pair a pillbox hat with a tailored dress or suit for that classic Jackie O look.
  • Wear a beret tilted to one side with a turtleneck and skinny jeans for a casual mod vibe.
  • Match a wide-brimmed hat with flowing skirts or coats to channel boho glamour.
  • Use bucket hats to add a playful, youthful edge to your outfit.

Final Tips from My Experience

  • Always try the hat on before buying if possible — comfort and fit matter as much as style.
  • Consider the occasion: some hats are more casual, others more formal.
  • Don’t be afraid to mix and match vintage hats with modern clothing for a unique look.
  • Take care of your hats by storing them properly to maintain their shape and longevity.

I hope my buying guide helps you find a 1960s hat that feels just right for you. Wearing these iconic styles has definitely added a fun and timeless touch to my wardrobe!

Author Profile

Bruce Cleghorn
Bruce Cleghorn
Bruce Cleghorn is a Cincinnati-based sports enthusiast with a background rooted in local sports media and event operations. Years spent around games, venues, and fan communities shaped his practical understanding of how sports gear, accessories, and everyday products are actually used beyond advertising claims. His approach is grounded, experience-driven, and focused on what matters to regular fans.

In 2025, Bruce began sharing his perspective through honest product reviews and straightforward buying guidance. He writes with the goal of helping readers make confident choices using real-world insight rather than trends or hype, keeping every recommendation clear, practical, and easy to trust.