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How To Wear a Hat with Long Hair

Sophie Diego

From berets to baseball caps, the coveted hat can do wonders in accentuating your final look. It could be your defining trademark—if styled correctly, that is.

For ordinary people, it’s just a matter of slapping on that final cap and calling it a day. But, it’s a lengthy trial and error process for the average trendsetter.

What hairstyle looks good with a beanie? How to wear a fitted hat with long hair? What outfits clash with certain types of chapeaus? The list goes on and on. 

If you find yourself in a styling kerfuffle, don’t opt for the simple choice of throwing your hat to the side. You paid good money for it, and it’s time to show it off.

This guide will show you how to fashion your berets, beanies, and newsboy caps in 12 different outfit ideas. Let’s get started! 

What is a Hat

Before we address the ‘how to wear a hat with long hair’ debate, it’s best that we define what a hat is in the first place. In short, it’s a type of accessory worn on the head. Whether that be a beret or a fez, they’re typically shaped and styled in different ways. 

Its purpose can strictly be for fashion reasons or as part of a uniform. For instance, the British guards at the royal palace wear bearskin caps. 

History of Hats

The earliest renditions of the hat date back to ancient Egypt. Civilians commonly wore kerchiefs to protect their heads from the sun. The royalty seemed to follow the same mandate, but they were widely depicted with helmet caps to signify the upper class. 

Obviously, if we were to scale forward thousands of years since then, the typical hat would have undergone a major style transformation—and it did in the medieval ages.

Women wore draped headdresses, veils, and turbans as a fashion statement and as a sign of modesty. Of course, men also donned hats as well—more specifically, the low-crowned brim. 

We won’t get into the entire history of the hat, but you should know that it held a significant place in Europe. From gentleman attire post the French Revolution to standard uniform practice for the workingmen, this simple accessory played a big role in society. 

Of course, its importance isn’t exclusively tied to white countries. India, Latin America, and the Indigenous people all use hats as part of their culture. 

When to Wear a Hat With Long Hair

Depending on the design, hats can be worn during certain ceremonies, occasions, and seasons. For instance, the classic beanie is commonly fashioned during the cold season.

In another example, the top hat is typically linked to galas and weddings. 

Basically, you can separate that hat into different categories: casual and formalwear. For those who can’t make that distinction, don’t worry; we’ll share some outfit ideas on how to wear a hat with long hair. 

How to Wear a Hat With Long Hair

It’s easy to throw on a cap and do nothing with your hair. But, if you’re anything like me—you might want to spice up your look. This may include donning a different hairstyle or cap.

It could also entail adding other accessories, such as statement earrings or a necklace. Obviously, you’ll want to find a hat that blends well with your outfit. 

Below, we’ll share some styling ideas if you’re wondering how to wear a hat with long hair. Don’t worry; we’ll be sure to offer fits for both men and women. 

12 Outfit Ideas with a Hat with Long Hair

Um, hello? Is anybody else getting Princess Diana vibes from this outfit idea, or is it just me? While Dynasty Di was known for her cute feathered shag, you too can rock her off-royalty look by opting to wear your hair down. 

We suggest curling it to give it some dimension. Since we’re opting for an uber-casual ensemble, a baseball cap, an oversized sweater, and a pair of biker shorts are an absolute must. 

If you’re a fan of the 90s bucket hat craze, we invite you to think outside the box when it comes to hairstyle ideas. Instead of leaving your hair down, why not opt for braids instead? 

Two lengthy pigtails can help accentuate the playful attitude of your outfit. Best paired with baggy pants, denim accents, and a white crop top, this is the perfect example of Y2K fashion done right. 

Nobody wears a long-brimmed hat better than Avan Jogia. It offers a sort of old-western feel to the entire look. Obviously, the best way to imbue those desert cowboy vibes is to leave your hair down.

We suggest zhuzhing it up using hairspray, a teasing comb, and dry shampoo.

 Instead of opting for cowboy boots and a white button-up tee, you play things super sage with a black trench coat, a matching hoodie, jeans, and a pair of beat-up combat boots. For those looking for hats for men with long hair, this is the chapeau to go for. 

The best way to figure out how to wear a hat with long hair is to resort to celebrity looks. Here, Harry Styles shows off his long locks paired with a classic Panama cap.

The black ribbon on the brim marries well with the striped button-down and the dark-wash jeans. Finished off with rings and a cross necklace, it’s definitely the outfit to go for if you happen to always be that ‘curly hair with hat’ guy. 

Having a bad hair day? A hat can do wonders in hiding those untamed baby hairs. If you’re looking for something more elevated, we suggest opting for a newsboy cap.

Ideally paired with a side braid, an oversized knit vest, and a black sweater underneath, you too can go London-girl chic. Just make sure to finish off your look with a matching Chanel bag.

If you can’t be bothered to brave those gusts of wind, it’s probably best to leave your hair in a bun. Since the coveted ballerina ‘twist’ is all the rage in season, we recommend opting for a more romantic ensemble. 

This outfit features a cream beret with matching trousers and a beige-colored cardigan. It’s simple, practical, and considered a great take on the capsule wardrobe. This is how to wear a hat with long hair. 

If you’re wondering how to style a beanie with long hair, we suggest leaving it unkempt and wild. The cable-knit chunk of the hat does well in taming the puffiness of your locks. 

For the rest of the outfit, a set of Vans, a pair of dark-wash jeans, and a laid-back leather coat are a must-have for those keen on looking super hipster. Of course, no coffee-boy look is complete with a pair of sunnies. 

For those in search of ‘straight long hair with hat’ outfit ideas, I’m sure this elegant ensemble can speak to your cold-season needs. This quilted bucket cap pairs beautifully with the espresso-stained trenchcoat and cream turtleneck. 

In order to frame the face, we suggest curling the ends of your tresses for a 1960s inspired look. It’s not pictured in the photo, but a pair of knee-high leather boots are a must to help complete the entire OOTD. 

Sophisticated, conservative, and undoubtedly elegant, this ensemble features a cohesive fit that centers around the bucket hat. It’s a great look if you want to look like a high-profile fashion editor hitting the best cafes in Paris. 

The printed neck scarf and the gold-tinted statement earrings are a must in order to frame the face. Since the ensemble is so ‘top-heavy,’ we recommend keeping things light by wearing a cream-colored trench.  

Balaclavas are all the rage this season. Why? Well, there is no definite answer—but I’d like to think it’s for warming purposes. Not only do they give you a fighting chance against those bitter winds, but they’re great for concealing bad hair days. 

We suggest tucking your balaclava under an oversized knit cardigan and fashionable trench coat. The colors are totally up to you, but a full, monochrome fit is highly recommended. 

Man buns were the highlight of the mid-2010s. Over the years, the fad has somewhat dimmed—but that shouldn’t prevent you from rocking this look regardless. 

This messy up-do totally works with a bright bomber jacket, a simple white tee, denim jeans, and a pair of streetwear sneaks. For those looking to go full hipster mode, we recommend a matching tote bag and a set of cool shades. 

If you’re looking to style a beanie with long hair, we suggest keeping your ‘do straight and uncomplicated. The simplicity of this hairstyle works intrinsically well with the subtle hues of this outfit.

The clean lines provided by the coat and jeans pair beautifully with the rest of the look. 

The oversized beanie is necessary to counterbalance the exaggerated silhouette of the jacket. In order to not lose your shape, we highly recommend finishing off your OOTD with ankle booties and a matching belt. 

What Type of Hats can you get?

There are hundreds of hats out there. Unless you’re an avid collector, we suggest sticking to a theme to help avoid wardrobe hoarding. Below, we’ll organize some styles into three different categories.

That way, you’ll be one step closer to answering the question ‘how to wear a hat with long hair.”

Casual:

Elevated, but casual:

Fancy:

How to Choose The Best Hat for Long Hair

Truth be told, there is no ‘one hat’ for long hair. It all depends on your current aesthetic and needs. For instance, the classic beanie is perfect for cold weather. Some trendsetters like to wear it outside of winter and fall, but very sparingly.

The beret is a great choice to have if you’re looking to implement elegance in your outfit, but it doesn’t work well if it’s just sweats for the day. 

Aside from season and style, choosing the best hat for long hair requires looking at three factors: price, quality, and material.

Obviously, caps made out of premium materials are usually the most expensive. Fabrics such as wool, denim, cotton, polyester, acrylic, and sometimes leather are used in baseball caps, berets, and beanies.

It’s important that you choose a design that’s quite hefty in weight. You don’t want a loose hat that could potentially fly away with the wind.

We can’t give an accurate estimate as to how much they cost, as it depends on the style. But, you should account for these features in order to make a smart purchase. 

How to Style a Hat With Long Hair

For those Googling ‘how to wear a hat with long hair,’ there are usually three different styling factors to consider: the hairstyle, the hat, and the outfit. 

If you prefer to leave your tresses down, you may want to curl or tease it in order to provide movement and definition. Those who opt to wear their hair up may wish to fashion buns, braids, or colored extensions if they want to make a statement. 

In our opinion, the hat is the make-or-break of the outfit. You’ll want to create a cohesive fit that matches the vibe of your chapeau. 

For instance, beanies pair well with flannels, jeans, and loungewear. Straw hats are synonymous with summer dresses and linen attire. The coveted wide-brimmed hat may inspire Dallas-themed outfits or old-western OOTDs. The options are ultimately limitless. 

Fashion Tips to Avoid When Wearing a Hat With Long Hair

You know what they say: beauty is in the eye of the beholder. In relation to fashion, some outfit ideas may appeal to others, but to some—they may not.

But, there are a few styling no-no’s that you should look out for. In the following segment, we’ll share some advice to avoid if you’re looking up how to wear a hat with long hair. 

  1. The horrible ponytail beanie: I get it; high ponytails and beanies don’t get along. But, I implore you—don’t opt for those silly beanies with a hole in place of a pom-pom. It creates a strange look that’s bound to turn heads for all the wrong reasons 
  2. The super floppy sun hat: the wide-brimmed sun cap is fine for beach days. What we’re referring to is the super exaggerated straw hat that covers an arm’s length of space. Not only does it look weird, but it also impairs your vision 
  3. The Y2K ‘side placement’: In the early 2000s, celebrities had this thing of fixing their hat on a ¾ angle. If you hate crooked paintings, you’ll immediately want to re-position styles like this if you see them on the streets 
  4. Buns with baseball caps: Let me get this straight. Wearing a low bun or a ponytail is completely fine with baseball hats. But, if you don a messy bun using the back closure as support, you’ve immediately locked yourself in a tricky situation. Removing the cap is near to impossible if you want to keep the hairstyle in place 
  5. Hats with loud prints, embellishments, and graphics: the best type of caps are the ones that are plain and understated. It helps if your hat is simple, as it usually pairs well with several outfits. Obviously, this tip doesn’t apply to those who love the maximalist aesthetic 

How To Take Care Of a Hat

So, you finally invested in a premium hat. In order to maintain its quality and shape, you’ll need to look after your cap properly. For those not keen on visiting their local cleaner, we’ll share some ways to best clean and store your precious hat. 

Best Places to Buy Hats

So, you finally figured out how to wear a hat with long hair. But where can you buy a high-quality cap? Below, we’ll feature some reputable stores and boutiques to support those currently in the market:

Final Thoughts

It’s time to abandon the belief that hats are an afterthought. In most cases, it’s relatively easy to base your entire outfit on a cap. From berets to fedoras, we showed you multiple ways how to wear a hat with long hair.

Obviously, you don’t have to go out and buy a new design in order to match your aesthetic, as it can easily be achieved by donning a fresh ensemble or hairstyle. In short, all you really need is some outfit inspo and a little bit of confidence. 

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