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

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How to Wear a Hat

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.

If you’re wondering what are the different types of hats available, what kind of hat you should wear, and how to style that hat in an outfit then this resource is what you’ve been looking for!

I’ll also share many photos of outfits with hats, so you have direct examples of what I am talking about and hopefully get inspired to take that hat out for a spin or finally add a stylish hat to your wardrobe.

Outfits with Hats

If you scrolled through this post already, you might be thinking Woah, that is a lot of outfits with hats! Yep!

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.

Scroll to the section that you want to learn more about or read the entire post if you’re curious as to how you can wear a hat year-round.

If you need to add a straw hat to your summer wardrobe take a look at Free People, I love the variety of summer hats they offer and the prices range from low to high.

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!

If your favorite pass time in the summer months is lying on the beach, you need a fabulous sun hat for your beach outfits. It’ll not only protect you from the sun, but you’ll look oh so stylish.

If you want to wear a hat in the summer look for hats that are lighter in color, like light brown, cream, off white, and white. Or a mix of colors, dark brown and cream or black and tan like in the hats I’m wearing in the outfits below. These two-toned style hats are very interesting. Or the hats with ribbons around the hat in a different color are nice as well.

The main material to wear in summer hats is straw. Don’t think that straw hats have to be country looking, no, straw hats are chic and stylish too. It’s best to wear straw because of the light material and keeps your head from getting too hot. You don’t want to wear felt, wool, or cashmere hats in the summer.

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.

When putting together summer outfits with hats the three things to remember is color, balance, and proportions. Since the summer and spring, hats are usually light in color consider how your clothes will either match or contrast the hat. If your hat is neutral you could wear neutral colors in your clothes so it all coordinates.

For example; in the black summer off-the-shoulder dress and brown and black hat outfit I’m wearing below, I brought the colors of the hat to my outfit which is why that outfit looks so balanced. Everything is coordinated.

Or you could play with contrasting colors and really make your hat the focus of the outfit. In the second outfit with a dress and hat, I loved the contrasting colors, the dark blue dress with white stripes and a bright white hat with black ribbon.

If you want to play with proportions with a large sunhat, keep the rest of the outfit sleek. You could wear a large flowy dress and a huge sun hat if that is the look you are going for but keep in mind you don’t want your outfit to drown you. Keep balance in mind. If you need more tips on balance and other outfit tips check out, How to Look Stylish Every day – Your 5 Step Checklist and How to Dress Classy – 7 Style Tips You Need to Know.

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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.

Don’t be afraid to play with styles. In the first spring outfit pictured below, I paired the Panama hat with a light, flowy white dress and denim jacket. The white dress is feminine and free, the jacket brings the outfit structure, and the hat adds some masculinity. Let’s not forget the sandals. The sandals add a pop of color to the outfit needed. Overall, the outfit is balanced and fun. Remember these points when putting together your spring outfits.

On the second summer outfit, I paired stripes and a large gold chain to play on the nautical theme but still keep a feminine look.

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.

Also, note that all the outfit examples are with different styles of shorts. From distressed denim shorts to pretty printed dressy shorts, the variety of styles of hats and outfits will provide you with outfit ideas for a variety of occasions. From wine tasting in a winery in Napa Valley to take in the sun rays at a beach.

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. This summer hat and outfit is one of my favorites!

On the opposite end of the outfit spectrum, you could pair a hat with simple jeans. This very casual look is something you can really wear at any time. If you wondering how to wear a baseball hat consider the outfit I put together below. I paired the baseball cap with a plaid shirt, white tank top, blue jeans, and boots. This is a cute hiking outfit I wore while exploring a lake in California.

I included these two different hat styles and hat outfits to show you how to pair a hat with a jumpsuit and romper. The first hat is a light boater hat with a pink ribbon that I paired with a bright yellow jumpsuit. If you have not worn jumpsuits before make sure to read: How to Wear a Jumpsuit – 5 Must-Follow Style Tips. This is a summer outfit I wore while traveling around Provence in France. I love wearing jumpsuits while traveling because they are simple and cute one-piece outfits so it doesn’t take up a lot of room in your luggage.

In the second outfit, I paired a large gray hat with a black romper. This is what I wore to Coachella one year. This outfit is super cute because of the pattern on the romper and the fun style of the look. This is not necessarily an outfit I would wear any day but if you’re going to a festival soon, here is an outfit idea.

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. Take a look at 20 Business Casual Outfits for Women [Ideas & Inspiration], for ideas on what to wear to work.

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. This is the reason I have three different colors of fall hats; forest green, gray, and red.

Scarves are a great way to add pattern and color to a fall outfit, you can coordinate the color with your hat or take a look at the color wheel to see which opposite color would look best. If you have many scarves in your wardrobe, check out Ways to Wear a Scarf & How to Tie a Scarf: The Definitive Guide for a lot of outfit ideas.

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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.

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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! As with all the style tips I mentioned above, keep your beanie outfits color coordinated. Either match the beanie color with something piece in your outfit or wear complementary colors.

In the first beanie outfit below, I’m wearing a light gray beanie that matches the light gray turtle neck. I wore a bright red vest for a pop of color because the rest of the outfit is black. There are only three colors in that outfit but a bright red vest and a variety of textures make this outfit interesting.

I wore the red vest again in the third outfit. This time instead of a gray sweater I swapped it for an off-white sweater and wore the same black leggings. If you usually wear leggings in the winter, I think you’ll like this style guide: What to Wear With Leggings & 20 Style Tips on How to Wear Them.

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. This criterion is especially important when it’s an investment hat. Taking the time and finding the perfect hat style for you will ensure that you look good in a hat!

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. I purchase hats at a variety of prices from $20 to hundreds, my hat collection has grown over the years and I continue to add to it but as you can see in this post, I use them a lot.

If you have long hair as I do and you don’t know how to wear a hat with long hair, scroll through the many hat outfits above and you’ll see that there are two main ways I style my hair with a hat. I wear my hair styled down, like in the picture below, this is my favorite way to style my long hair with a hat but it’s the most time-consuming. I also braid my hair, this can be one braid or two braids. They are very loose braids so my long bangs frame my face. I don’t like pulling all my hair back away from seeing it because then it looks like I have no hair and that’s not a style I like.

I hope this guide on how to wear a hat has given you plenty of outfit ideas and inspired you to give different types of hats a try!

Let me know in the comments what are your favorite hat styles are and how you normally wear them!

Also, which of the many outfits with hats above is your favorite? I would love to know!

Stay Stylish,

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