40+ Outfits with Hats: How to Wear a Hat with Style & Ease!

Hats Outfits

Stylish Hats!

Stylish hats! They are one of my favorite accessories! Along with adding some pizzazz to an outfit, a hat can completely change a look. An outfit can go from simple to interesting just by adding a stylish hat. If you're wondering how to wear a hat or how to look good in a hat, that is why I put together this guide, this style guide is for you!

First, wearing a hat isn't all that difficult. Plop it on your head, and you're good to go. It's not how you wear a hat necessarily but what you pair with your hat, it's the outfit itself.

Since a stylish hat is an accessory that you can wear in the Winter, Spring, Summer, Fall, and even while traveling, this is something you could slowly start adding to your wardrobe and wearing once in a while, if you haven't already.

Outfits with Hats

I did say in the first sentence that stylish hats are one of my favorite accessories! I wanted to show you a wide range of outfits with hats to inspire you throughout the year. So the following images are broken down by season — spring and summer than fall and winter.

Stylish Summer and Spring Hat Outfits

In the summer you're given to green light to bring out your most wide-brimmed sun hat! Wide-brimmed hats make wearing a hat in the summer so much fun! So don't be embarrassed, be confident!

The different types of hats you can wear in the summer include a boater hat, sun hat, wide brim hat, Panama hat, straw fedora, bucket hat, and of course a fashionable baseball cap. These types of summer hats are the main categories and you will find a huge variety of styles within these main types of hats.

Summer Dress and Hat Outfits

A Panama hat is a stylish option for the Spring season because it adds a masculine touch to the delicate pieces of Spring. The juxtaposition of masculine and feminine makes for attractive spring outfits.

There are ten different hat and dress outfits below to show a variety of outfit ideas and inspiration.

How to Wear a Hat with Shorts

In the hat outfits below I'm wearing 6 different types of summer hats. To a wide-brimmed sun hat to a two-toned fedora, this section really shows you the variety that you can achieve in these looks.

The first two outfits show you what to wear with white shorts, simple but cute outfits you can wear to the beach or while exploring a seaside town. The third outfit is very boho casual with a white flowy top with cute pattern, chino shorts, neutral fringe bag, and of course a brown and black straw fedora.

How to Wear a Hat with Pants in the Summer

You can go from very nice to very casual depending on the types of pants you want to wear. In the first hat outfit as you can see it's on the nicer side. I'm wearing a pair of super cool vertical striped pants I purchased in a little boutique in Greece, with an off-the-shoulder white top, the famous Bali bag, and a white fedora.

A hat can completely transform an outfit from simple to interesting. Don't be afraid to experiment with different styles!

Stylish Fall Outfits with Hats

Fall is my favorite season to wear a hat! They look stylish with every outfit and something about the time of year makes wearing a hat very stylish and you'll always look good in a hat in the fall.

In the Fall, you can wear a hat with anything you wish. Jeans, dresses, blazers, skirts, you can even dress it up with trousers and heels. I wouldn't necessarily wear a hat to work but if you're going to an after-hours or weekend event, with the right outfit it would look amazing.

Wool or felt fedoras are my favorite style of hats to wear. Also, look for fur felt fedoras, a bit more expensive but the hats are high quality, and you'll keep them forever. That said, you don't have to spend a lot to find a stylish Fall hat. Most of the hats I'm wearing below are $50 or less.

How to Wear a Winter Hat

When wearing a hat during the winter, you'll most likely be pairing it with your coat, sweater, cardigan, or scarf. If you're only purchasing one hat make sure you find a color that goes with many winter pieces in your wardrobe.

Beanie Outfits

Beanies! I added beanies to this post because they are a type of hat. They keep your head warm in the chilly days of winter and these like sun hats are necessary.

When shopping for cute beanies I usually stick to neutrals or deep colors like forest green or burgundy. As you can see in the beanie outfits below I love beanies with the little pom on top!

How to Look Good in a Hat

If you have never worn a hat and don't own one yet find a local shop that specializes in hats. If you're not sure which hat to purchase during your first visit, don't rush. Try on as many styles as you can, take a photo of you wearing the hat, think about it, and make sure you love it before buying.

Only invest in hats if you know you'll wear them a lot. Some hats can be pretty expensive as a true Panama hat can cost hundreds of dollars. A Panama hat is Peter's favorite type of hat so every couple of years we purchase a new one and each costs about $200 to $300.

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