How-To: Wear Hats! (Because You Should)

Q. Hi, Jordan!

I love hats. I would wear a hat every day if I could, but I have a problem: I can’t figure out how to wear them. Any advice?

– Steph

A. Oh, I used to be so not into hats. I didn’t think they looked good on me, and besides, every time I wore one I was just so aware of the thing, and felt like everyone else was, too. “Oh, that girl? You mean the one IN THE HAT?” Sort of like that.

This is me on the way to the airport at five in the morning last March (this trip), literally in the process of discovering that Hats Are Fun. I had bought a straw fedora in a moment of wild, reckless abandon (I know: so wild! so reckless!), and then when I was packing realized that the trouble with the thing was that there was nowhere for it to go save for on my head. So I was sort of forced into wearing it with a completely ridiculous outfit, and discovered that I quite like the drama of odd hat/clothing pairings.

Anyway, in the months since, I have wholeheartedly embraced this new world of accessories, and think you should give it a shot, too.

When it comes to hat-wearing, I generally stick to three basic categories:


(This is one of my favorite outfits in my closet. I think it’s mostly the snazzy hat’s fault.)

The key to this look is choosing a hat with gorgeous details, like a beautiful ribbon around the brim, a great shape, or something a bit over-the-top like a plume or crystal accent. The rest of the outfit can be as simple or as mixed-up as you like, but it should all have the feel of being fairly done. This is not a hat to wear with your sloppy sweats.

As a finishing touch, add sunglasses (totally unnecessary; so fun) and give your hair a bit of a style – at the very least, rub product through the ends or spend a few seconds with a curling iron. If you want to get crazy with it, pull your hair into a side bun underneath your ear. That’d be pretty.


Big, furry hats – or any others that fall into the “Completely Bizarre” category – are a look you have to commit to.

It’s a new one for me, the HELLO, I AM WEARING A RIDICULOUS HAT look. But I like it.

With a hat like this, I’d keep the rest of the outfit pared-down in terms of color and pattern, and stick to minimal accessories. While in the above shot I’m wearing the hat with purple velvet lounge pants, which are sorta over-the-top themselves, the look works because the clothing is all fairly streamlined and has a simple, clean shape to it. Plus, an off-the-shoulder sweater keeps the focus right where it should be: on your face (and the thing sitting above it).




This, of course, is the easiest category, and an excellent way to get in a hat-wearing state of mind if you’re wary of the idea. Winter picks are obvious – big, chunky knits, pom-poms, things like that – but it’s a little bit more of a leap to grab a hat when it’s steamy out. But you should; it’s a great solution for hiding less-than-lovely summer locks and keeping away those terrible UV rays. And besides, it’s an easy way to give style and polish to an otherwise verging-on-boring outfit like a tee and shorts.

While we’re on the topic, want to see my Hat Party Trick? Here you go.

Click images for additional outfit info; hat product info after the jump.

SNAZZY: Albertus Swanepoel for Target, Mossimo Supply Co., TopShop

COMPLETELY BIZARRE: Target Natural, Albertus Swanepoel, Mossimo

SEASONAL: TopShop, Mossimo, TopShop, Mossimo

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