When we think of vintage or retro, what comes to mind? Elegance. Class. Timelessness. Style.
Thoughts of old Hollywood stars wearing beautiful headwear and stylish fifties women in hats that turn heads. But not every hat from the past was a fashion win.
Some hats were just plain weird. Others were too over-the-top to ever be considered good. A few were so ugly, we still laugh about them today.
Let’s look at 10 of the ugliest hats and headwear styles that made their mark in fashion history for all the wrong reasons.
 |
| Ugly hats. Unhappy faces. (Image, CHATGPT-generated) |
Fez Hats
When: 1800s and later in pop culture.
What they looked like: A round, flat-topped red hat with a tassel.
Why is it ugly? Because it looks like a fancy flowerpot with a string. The fez became popular in vintage men's fashion, but let’s be honest, it makes most people look like they’re trying too hard to be quirky.
 |
| Fez hat (Source: Wikimedia) |
Conehead Hennins (Medieval Princess Hats)
When: 1400s (Middle Ages).
What they looked like: A Tall, cone-shaped hat with fabric hanging down from its tip.
Why ugly? This hat made your head look like a traffic cone. Medieval noblewomen wore them to look elegant, but to be honest? They just looked silly, like stupid birthday hats gone wrong.
Neon Plastic Visors
When: 1980s and 1990s.
What they looked like: Bright, see-through visors worn for sun protection.
Why ugly? Because the retro-style hats made you look like a lifeguard in a kids' cartoon. They didn’t block the sun properly. And the colours? Lawd! They were an eyesore and came in weird colours, like Neon pink, green, and orange.
Bejewelled Trucker Hats
When: Early 2000s.
What they looked like: Foam-and-mesh trucker hats covered in gems or glitter.
Why ugly? Trucker hats were already bad. Adding fake jewels and glitter words like “Diva” or “Hot Mess” didn’t help either. It was a confusing mix of glam and gas station fashion.
Coonskin Caps
When: 1700s and two centuries later, in the 1950s (thanks to TV shows).
What they looked like: Hats made from animal fur, often with the poor creature's tails attached.
Why ugly? These hats looked like a raccoon was napping on your head. They were meant to show you were outdoorsy, but rather, they made you look like you forgot to finish dressing for the costume party.
Pillbox Hats with Netting
When: 1950s to 1960s.
What they looked like: Small, round hats that sit on top of the head, often with a short veil made of netting.
Why ugly? Some people successfully pulled these off (hello, Jackie O). But most pillbox hats looked like you were balancing a frosted cake on your head, with a little net curtain that didn’t actually do anything but look out of place.
Flowerpot Hats
When: Mid-20th century (1950s).
What they looked like: Hats shaped like actual flowerpots, without the plants.
Why ugly? Because they really looked like flowerpots. These retro hats were stiff and clunky, sitting too high and too awkwardly on the head. Not flattering. Not fun. Just weird.
Fur-Lined Bucket Hats
When: 1990s and 2000s.
What they looked like: Floppy bucket hats lined with fake fur.
Why ugly? Imagine wearing a fuzzy slipper on your head. That’s how ugly this hat looked. It was hot, heavy, and so un-stylish, unless you were trying to look like a confused teddy bear.
Mini Fascinator Hats
When: The Early 1900s to the present day (still seen at weddings and horse races).
What they looked like: Tiny hats or decorations on a headband, often with feathers.
Why ugly? Because they looked so comical. These tiny hats often resemble a craft project gone awry. They're too small to be real hats, and too loud to ignore. Great if you don't mind people asking, “What is that on your head?”
Oversized Puff Berets
When: 1980s.
What they looked like: Large, soft, puffy berets.
Why ugly? The hats looked like someone had put a pillow or a giant croissant on your head. They were big, heavy, and never sat right. More like baked goods than fashion.
Weird Hats, Off Forever
Fashion wasn't, and sometimes, still isn’t always pretty, and these ten headwears prove it. Over the years, some trends just never made sense, and definitely didn’t age well. While we love exploring retro styles and vintage-inspired fashion, not everything deserves a comeback.
These ugly hats had their moment, but we are happy to leave them in the past, or at the bottom of the fancy-dress costume box.
Copyright © Viryabo 2025. All rights reserved.
Other articles of interest
7 Famous Fashion Designers of the 1960s
No comments:
Post a Comment