Hat and Outfit Pairings
January 03, 2022

7 Types of Hat and Outfit Pairings

Hats have held their place as stylish accessories for men and women for decades. The types of hats available today have diversified to the point there is a hat for every occasion. Hats shelter the eyes from the sun, keep heads warm and dry while complementing looks.

Different types of hats can be paired with different kinds of outfits, such as casual, semi-formal, and formal wear. When you shop for a hat, you should make sure it is perfect for the outfit you intend to pair it with. Also, I recommend you find a hat that looks good on your face.

You can also choose to create custom hats to make your matching more personalized.

Custom hats

Below are types of hats and the best outfit pairings for them.

1. Panama Hat with a Beach Outfit

Panama hat originates from Ecuador. Hand-woven using plaited leaves of the toquilla palm plant, it is sturdy and easy to wear. These hats are light in weight and are typically white in colour. Another admirable feature of these hats that make them a perfect accessory to wear on summers and seaside is their breathability.

Panama hats are a common sighting in tropics and seaside areas that enjoy warm weather most of the time. So, what is the best outfit pairing for a Panama hat? Due to the relaxed style of Panama hats, they blend perfectly with light-coloured summer clothes such as a white linen dress, shirt or a floral summer shirt on a beachy backdrop.

You can wear this hat to summer parties, pool parties, brunch parties or any warm-weather event. Do not attempt to wear a Panama hat during the winter.

2. Fedora with a Classy Outfit

When appropriately paired, fedora hats scream great style and superior taste. Fedora hats are a classy accessory worth pairing with a classy and elegant outfit. Fedora hats were once the most worn hats in the business world. However, the appeal of fedora hats has broadened since then.

Fedoras have a slight pinch at the front top part of the crown. When paired with a well-fitting suit and tie, a fedora hat brings out an elegant look. Fedora hats are available in various sizes and colours. However, it would be best to stick to medium-sized fedoras with a neutral tone to have a more classic appeal.

The fedora is best paired with tailored pants and long coats. Occasions that are best suited for this kind of hat are weddings and dinner parties. Fedora hats do not look good when paired with casual wear such as jeans and sweaters.

3. Beanie with a Fall-Winter Outfits

The beanie is a brimless, knitted hat designed to keep the head warm and comfy during cold weather and winter. The beanie has a casual look that brings out a relaxed aura. Nowadays, there are various beanie styles that make the hat perfect for pairing with different outfits, even in summers.

Beanies are worn mainly by musicians, dancers, actors, designers and writers. You can pair this versatile accessory with knitted winter woollies, zip-up hoodies, and streetwear.

It is best to find a beanie with a neutral colour and thin material for versatility purposes.

4. Baseball Cap with Casual/Sports Wear

Baseball caps have withstood the test of time and still remain a great accessory up to date. Back in the '90s, baseball caps were worn backwards (snapbacks). However, the trend is long dead, and baseball caps look great when worn facing the front. You can also check this out If you find yourself wondering what the best low crown hats for small heads are, you’re not alone.

There are numerous variations of baseball caps. However, they all have the common features: rounded crown and stiff front brim. Baseball caps are versatile, and they bring out a mature look.

With the embroidered patterns and prints, a baseball cap brings out a stylish look when paired with an unexpected outfit such as denim, pantsuit, cargo pant, cocktail dress and a pair of Chelsea boot or high-top sneakers to complete the look. These custom fitted hats embroidered can also be paired with sportswear when heading out for a sports activity such as golf, baseball, morning jog, or lawn tennis.

5. Bucket Hat and Streetwear

Bucket hats were commonly worn by fishermen. However, they have made a strong return and are a common feature in Asian fashion. The flexibility of the bucket hat makes it easy to carry it along when travelling.

The brim slopes downward, making it a good sun protection accessory for people with pale skin tones.

A bucket hat is a street style favourite because of the laid-back urban look it creates. A bucket hat pairs well with casual and street wears. You can rock your look with a bucket hat by pairing it with a bomber jacket, oversized blazer and jeans, jersey, mini skirt, high-top, graphic t-shirt, leather jacket and a pair of joggers or sneakers.

6. Cowboy Hat and a Cowboy Outfit

Cowboy hats are among the most popular hats, if not the most popular hat in the world. It is a symbol of American fashion. A cowboy hat is recognised for its tall pinched crown and wide brim. Cowboy hats are commonly worn by cowboys and ranchers.

Nowadays, cowboy hats can be worn by pretty anyone. However, to bring the best appeal out of a cowboy hat, you should pair it with jeans, a pair of cowboy boots, a tucked-in button-up shirt or tank top, a leather jacket and a buckle belt. If possible, you can also fake a southern/Texan accent.

7. Pork Pie with Smart Casual Outfit

This list cannot be complete without including a pork pie hat. Pork pie is closely similar to fedora. It has a medium-sized flat crown and a short and slightly curved brim. Nowadays, it is worn mainly by hipsters due to its modern yet classic and artistic appeal.

If you are tall, the pork pie is the best accessory. Its short, flattened crown makes it ideal for someone who wants to look stylish but does not want to add more height. If you're going to wear casual clothes but still want to look formal, you can pair a pork pie hat with a blazer, preferably a navy blue one, jeans, khaki pants, a button-down shirt, or a pocket squared suit and simple flat shoes finish the look.

If you are a woman who wants to nail it with a pork pie, you can pair this flat cap with a patterned nylon stocking and a short skirt.


A hat is an essential accessory. There is a hat for every occasion. You need to know which hat to wear to which occasion and the outfit it goes well with. A Panama hat rocks well with a beach outfit, and a fedora is best suited for a classy outfit such as a well-fitting suit and tie. If you are tall and want a hat to match your smart-casual outfit, a pork pie hat is the best accessory for that.

7 Types of Hat and Outfit Pairings