How to Wear Retro Hats and Fascinators

A stylish hat can convey so much with so little. Hats can be demure, bold, quirky, and classic. They can combine modern and vintage styles into a cohesive look. Many people don’t consider hats when cultivating their look, but a retro hat or fascinator is a simple way to discover your own Easy Retro Style.

My friend Lindsay from Maman Loup’s Den didn’t dub me “The Curious Cat in the Hat” without reason. I love incorporating a sassy hat into my wardrobe and giving an outfit a new life.

When I receive compliments on my retro hats, they are often followed by, “But I could never wear that.” Except they’re wrong. Anyone can incorporate easy retro style with hats – from fascinators, to fedoras, to cloches, to pillbox – with a little imagination. If hats feel intimidating, fascinators and headband hats are a simple, affordable way to start.

My mom gifted me a selection of vintage hats years ago and I’ve always been slightly obsessed with them. I used them as decoration for a few years until I finally worked up the courage to try one with a Sunday dress. My ultimate dream is to become my own milliner, creating hats for myself. Until then, I use Sunday as my #HatSunday on Instagram, often wearing easy fascinators purchased from Amazon or the thrift store.

Tips for Wearing Retro Hats and Fascinators

1. Don’t Go Costume. You can, of course, recreate a whole era from  head to toe if you’d like. Most of the time, however, retro style is a nod to the past with modern interpretations.
2. Mix and Match. I don’t live in the past, so I’m not worried about doing an exact replica of a look from one era. Don’t be afraid to mix a vintage hairstyle from 1940 with a hat from 1950 and an eyeliner trick from 2017.
3. Plan Ahead. Sometimes I style my hair first without thinking about which hair accessory I want to wear with my outfit. Victory rolls are amazing, but they don’t work with all hats. I recommend pairing your hat or fascinator first, then styling your hair to compliment your accessory.
4. Have Fun! Wear hats as a way to develop and complement your own personal style. Play around with hats. Wear a hat with a sweater and jeans. Place a fedora on your head on a day when you don’t have time for make-up, but you want to have fun with your look.

What’s your favorite hat style?