How to Wear An Absurd Hat Without Looking Silly

There is a hat for everyone.
Publish date:
September 9, 2014
shoppables, hats

I seriously love hats. From tiny impractical little fascinators to gigantic impractical Edwardian touring hats, I love ’em all.

Now I’m sure many of you like hats also, and would like to wear hats but don’t know where to start, or are worried about being overwhelmed by an elaborate hat, or are just generally nervous about the whole thing and want instructions from your favorite Internet beauty and fashion comedian, me. (I know I’m your favorite one because it’s a thing I just made up and there aren’t any others.)

So now on to my usual hyperactive list based format:

1. Acquiring a good absurd hat can be hard. There is a lot of flimsy plasticky overpriced garbage out there and that’s not we want, now is it? Telltale signs of a crappy hat are:

  • The use of “silk” and by silk I mean polyester flowers and cheapo beads
  • A crappy hat base, so be sure to check under all the frippery and frills to see if there’s an ugly premade base hiding on the underside of your Gibson girl fantasy piece.
  • If it looks like there’s a cheap feather boa on top of it, there is.
  • Cheap overly shiny costume satin. It’s just so sad and ugly.

2. If you’re going to be wearing an elaborate hat, the rest of what you’re wearing should match the hat. A dainty feathery fascinator just doesn’t work with jeans and a T-shirt. It’ll end up looking like a party hat your friend forced you to wear at her ostensibly fun birthday party. Make sure your look matches and is as dramatic as the hat, so as not to allow the hat to upstage you. (You have to show the hat who’s boss.)

3. Choose a hat that works with what you’re doing. Choosing something with a lot of plumes sticking up off it is probably not the best choice for movies, crawling through tight spaces or limbo competitions. Similarly, a veiled hat is not appropriate for sharp shooting, badminton, or to wear when performing open heart surgery. However, veiled hats are very appropriate for beekeeping. In all seriousness, choosing a hat that works with the weather and whatever it is you’re doing that day will make life a lot easier and more pleasant.

4. Start out with hats that match a lot of your wardrobe. For most people, this means neutrals, however if you own 75% pink and 0% beige, a pink hat is definitely a better bet than a beige one. Adjust to suit your own color palette. For me, this means a lot of black and gray, and a fair amount of pink and red. For you it could mean an endless sea of seafoam green and teal which is fabulous. This way, it’ll be easy to make outfits around your hats.

5. You’re not a hat person? Yes, oh yes, you are! There is a hat for everyone. Hats come in all sorts of shapes and sizes and so no matter what shape your head is, there is a way to make hats work for you. My husband looks terrible in most hats, but a certain style of cowboy hat looks absolutely fantastic on him. (Also fascinators, he looks really good in fascinators). Try on shapes and sizes of hat, figure out what you like, experiment with hairdo/hat combos. You will eventually find something that just clicks and looks magnificent on you, and you’ll never ever want to take it off.

6. Be confident in that hat. You don’t look silly, you look amazing. Rock that hat as hard as you can, strut down the street, bask in the compliments of a non-hatted world. That hat makes you look elegant, and put together, but also creative and with loads of joie de vivre. You’re fabulous, I promise.

You too can wear hats, hats of many sorts with lots of frills and feathers and decorations. You will look awesome. In parting, here’s a picture of me in my Mary Poppins hat.