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Top It Off with Vintage: A Guide to Styling Hats from the Past

Classic hats from bygone eras are the perfect way to add a splash of retro charm to modern looks. Vintage headwear brings us back to more genteel times when hats were a staple accessory. While mainstream hat wearing may have waned, vintage lids deserve a revival of their own.

This guide will explore popular hats throughout the decades of the 20th century. I’ll highlight what made each style iconic and offer tips on how to incorporate vintage hats into your everyday wardrobe and special occasion outfits. Let’s delve into the world of splendid hats from the past!


1920s Cloche Hat


The archetypal headwear of flapper fashion, cloche hats were snug-fitting and rounded, with the brim pulled low over the forehead. Typically made of felt, the cloche contoured neatly to the head, showcasing sleek finger-waved hair. Cloche styles can lend a glam yet garconne air to modern dress. Opt for cloches in felt or wool and in solid colors or subtle patterns. Pair with a shift dress and Mary Janes for a 1920s look. For everyday wear, don a cloche over curls or a bob with casual dresses or jeans. Finish the look with brooches and feather details.

1930s Turban


Turbans emerged as chic headwraps in the 1930s, influenced by exotic locales and foreign intrigue portrayed in films. Silk and velvet turbans added drama and mystique to the decade’s sleek, bias-cut gowns. The turban is quite versatile today. Wrap one over curls in a retro hairdo or simply over straight locks. Choose a printed style and let it stand out as the focal point. Or go for rich solids like ruby red or midnight blue velvet. Pair with cocktail attire or feminine day dresses.

1940s Fascinator


Whimsical fascinators adorned women’s hairstyles in the 1940s. Small cocktail hats with netting, flowers, feathers or veiling were perched upon updos and pinned in place. Lavish trimmings added playfulness during wartime austerity. The fascinator makes a perfect accent for weddings and events. Opt for vintage-inspired styles decked out in satin ribbons, netting or floral details. Colourful fascinators look lovely with tea dresses. For a more formal do, choose one in jewel tones or with crystal beading to complement an evening gown.

1950s Pillbox Hat


Named for their open, box-like design, pillbox hats resembled small caps sitting atop the head. They were made rigid and round, typically of felt or wool. The simplicity offset the decade’s fuller, New Look skirts. Pillboxes remain eternally chic. Wear one tipped forward or back on the head and secured with a partial veil for vintage flair. This petite hat complements both professional wear, like a suit, and casual styles like trousers and a shirt. For retro charm, go for a ladylike colour like mint green or pink. Finish with gloves and a pretty frock.


1960s Newsboy Cap


In the 1960s, women embraced menswear-inspired hats like the newsboy cap. This rounded hat with a centre dent and button top was popularised by new wave and punk rock culture. Newsboy caps imparted a cool beatnik tomboy vibe. The newsboy cap offers a casual vintage-infused option for weekends and off-duty days. Try one in soft felt or wool. Corduroy and twill give textural interest. Pair your newsboy with relaxed fitted blazers, slouchy trousers, band tees and sneakers for an eclectic look. Top your cap with mirrored aviator sunnies.

1970s Wide Brim Sun Hat


Floppier hat forms came into fashion in the hippie-influenced 70s. One key style was oversized sun hats with broad brims of 6 inches or more to provide ample shade. Natural materials like straw added laidback appeal. Bring back the chill sun hat style for picnics or festivals. Look for a wide-brimmed hat shaped of woven straw, raffia or linen. Brimmed hats flatter most faces but still allow hair to cascade. Pop one on with breezy boho dresses or high-waisted denim. Finish with artisan jewellery pieces.


1980s Visor



The plastic visor became a popular hair accessory in the fitness-focused ‘80s. These mini brimmed hats sat towards the front of the head, shielding the eyes and forehead. Visors came in bright colours and neons and sometimes featured athletic brand logos or pop culture icons. Channel sporty 1980s style with a plastic visor in a bold or pastel hue. Pair it with a leotard, high-cut biker shorts, and legwarmers for an aerobics class look. For a modern take, wear a visor with a graphic tee, jeans, and sneakers. Seek out fun retro logos like ‘80s bands, movies, or patterns. Keep hair long and loose, as visors were worn with voluminous locks.

1990s Bucket Hat



The bucket hat - a casual reversible hat with a wide, downward-sloping brim - became ubiquitous in 1990s fashion. Typically made of cotton canvas or nylon, bucket hats were worn by hip hop artists, skaters, and celebrities alike. The laidback hats exuded a streetwise, sporty vibe. Bring back ‘90s flavour with a bucket hat in canvas, denim or knit. Pop one on with high-waisted mom jeans and a crop top for a retro casual look. For extra ‘90s edge, choose bucket hats featuring logos of vintage sports teams or bands. Keep the rest of your look minimal to let the bucket hat shine. This reversible style offers sun protection with plenty of attitude.

How to Make Hats Work Today

Vintage hats add panache and personality to all types of modern outfits too. You can channel retro charm while staying firmly in 2023. Here are tips to make hats work seamlessly today:

  • Choose hats in classic materials and patterns without over-the-top trimmings.

  • Style wide-brim sun hats with casual attire for weekends and holidays. Save smaller fascinators and pillboxes for events.

  • Match your hat hues and materials to the colour story and textures of your outfit.

  • Let hats complement your hairstyle rather than compete. Show off sleek updos or wear with loose hair to soften the look.

  • Tilt hats slightly rather than pulling brims low over your eyes. Angle them to flatter your face shape.

  • For formal events, coordinate your hat with other accessories like gloves, handbags and jewellery.

  • Stick to one statement per look. Avoid overloading your outfit with multiple bold items like hats, fascinators, bold prints, bags, shoes etc.

Immerse yourself in past millinery and rediscover the magic of hats. With the right style and savvy tips, you can wear vintage hats seamlessly today. Topping off your look with retro headwear adds timeless class and flair.


Until next time

Emma x






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