How to Wear a Hat Without Looking Like a Nerd

Have you worn a hat recently?

Most women I know have a love/hate relationship with hats. On one hand, they are the fastest way to cover up a bad hair day (or non-showering week) and, if done well, can invoke style in a way other accessories just can’t compete with; on the other hand, they can be tricky to wear without looking, well, nerdy. We’ve all been there—you leave the house feeling like you finally nailed this hat thing, only to walk by a window and realize you look more Lord Grantham out for a day of hunting than Lady Mary at tea and, actually, you were hoping to not look like any character from Downton Abbey, but instead like Jessica Alba at her most effortless, breezing into a meeting and taking charge while eliciting “oohs and ahhs.” Not that I’ve put any thought into this at all.

Fortunately, there are a few tried and true tips for how to wear a hat that, if followed properly, will turn you into a hat aficionado, able to wear hats in any season with any outfit. I’ve put together some of this season’s hottest hats with tips that apply pretty much across the board. So quit showering and go get yourself a hat! Check them out in the slideshow.

More Style Tips:

How to Wear a Hat Without Looking Like a Nerd

Knit Hat

...as worn by Hilary Duff

It's winter and it's cold and you absolutely should be wearing a hat (although I'm also partial to this fluffy ear muff, but that's a story for a different day), and there's nothing more on trend than a beanie ski hat, especially when worn indoors as part of your outfit. Yes, you read that right. In an effort to curb unsightly hat head, fashionistas everywhere are taking their knit hats inside, which for a mom like me is pretty much an open invitation to never shower again.

Hot tip: Always pull some hair out from the hat even if you're wearing a ponytail or your hair back. It will soften the look and frame your face nicely.
Round Wool Fedora

...as worn by Leanne Barlow

This season round hats are everywhere and for good reason---they're easy to wear and work with just about anything. Pair them with jeans and an easy tee for a cute playground look, or take it up a notch with a casual dress and boots for lunch with friends (a girl can dream). It's the perfect hat for hair that really could do with a wash but has enough bounce you're pretty sure you can make it another day.

Hot tip: You guys probably aren't going to like this, but one of the biggest mistakes people make when wearing hats is not doing their hair. I'm not saying it has to be perfectly styled or you have to try too hard, but most hats complete "a look," and part of that is often your hairstyle. Go for a hat on a second day of hair when it still has some structure or after you've let it air dry with product.
Beachy Straw Hat

...as worn by Jessica Alba

There is nothing more perfect for the beach than an easy straw hat. It keeps the sun off your face and the sweat out of your hair, and it ups your glamour quotient immediately. Throw on a pair of big sunglasses and order yourself a fancy drink to complete the look.

Hot tip: There's nothing worse than getting to your vacation locale and finding your new hat was squished in the suitcase (and who wants to have to carry it on?). Instead, buy a rollable straw hat that is virtually indestructible and will hold its shape throughout your travels.
Traditional Fedora

...as worn by Sienna Miller

Fedoras are one of those hats that never seem to go out of style. They're easy to wear and instantly take your outfit from ho-hum to adorable. And, like baseball caps and beanies, you can throw back a ponytail (with a few pieces pulled out on the sides), toss on a fedora, and be ready to go. (Who knew I was going to be so bossy when it came to how you can and can't wear your hats?)

Hot tip: A fedora should be easy and casual; it's a hat where you don't want to try too hard. Pair it with your favorite pair of jeans and flats in fall or shorts and a T-shirt in summer for a look that says you're all about relaxed vibes.
Baseball Cap

...as worn by Amber Fillerup

Personally, I feel like baseball caps are something you can either pull off or you can't. No matter how hard I try I always look like a Real Housewife whose newest boyfriend is really into baseball, while my sister can put on the same hat and look like your favorite girl next door. I say if you can do it, embrace it. And if you can't, well, nobody ever got thrown out of a game for wearing a fedora.

Hot tip: I know you guys know this, but the lady over in Section 21B didn't seem to at the last Bronco game I attended---baseball caps should be worn with sporty or casual clothes. That's all.
Floppy Hat

...as worn by Fit Fab Fun Mom

I love a floppy hat. Paired with a scarf and boots, it's about as glamorous as a gal can get. But I need to post a caveat: Floppy hats can be tricky to wear, mainly because you really have to commit to an outfit. (I know, hats are actually more work than they seem!) This isn't the hat to wear when you're in a rush to get out the door (see: fedora, beanie, baseball cap); this is a hat that takes some planning but is totally worth it in the end.

Hot tip: This is the time to wear your heeled boots, dramatic scarf, and over-the-shoulder cape. Floppy hats are all about drama, so feel free to play the part.
Round Straw Hat Fedora

...as worn by Design Love Fest

This is the sister to fall's wool version, and it's just as versatile and fun. Pair it with an easy sundress or jeans and a tank top for a look that says fashionable summertime fun.

Hot tip: Summer is all about ease, and this extends to hats. Think of your hat as a bold summer accessory, the same way you would a large necklace or over-the-top earrings, and keep everything else nice and simple.