How to Wear a Hat
Haley Snow
Table of Contents
I once described my romantic partner as a hat. Okay, now hear me out. I did so because unlike pants, tops, or shoes, which are necessary attire to engage in everyday life, a hat is a bonus.
We, as individuals, are required to meet our own needs without relying on a romantic partner. So, like a hat, the addition of love and partnership in our lives is extra.
It’s something special that makes the lives we’ve established on our own just a little bit better—a little bit more fun and exciting. So that’s why this analogy makes sense.
Now that we’ve decided that life is better with a hat, the next question we must answer is how should I wear a hat? Knowing when, where, and how to wear a hat is vital.
So, in this article, we’ll give you lots of style tips and advice so that you’ll learn how to put together a stylish ensemble.
And, after reading this guide, you’ll know how to wear a bucket hat, a baseball cap, a cowboy hat, and more.
What Is a Hat?
Before we dive into this ‘how to wear a hat’ guide, there’s one question we must answer—what is a hat? The answer to this question is straightforward.
Put simply, it’s an accessory that you wear on the top of your head, but you already knew that.
The real answer to this simple question is rather complicated since a hat is actually an incredibly multi-faceted thing. Hats have many functions, and we list a few of them below.
And when you’re trying to figure out how to wear a hat, knowing the function and purpose of your hat is key.
- Utilitarian: A hat is, in many ways, a tool. It keeps the sun out of your eyes and off of your face in the summer heat. And it keeps your head and ears warm during the cold winter months. Its initial purpose was one of practicality and protection from the seasonal elements.
- Status Symbol: For centuries, the type of hat a person wore was an indicator of their social status. Like all clothing and accessories, it was a visual symbol of one’s wealth, (or lack thereof), profession, and which rung of the societal ladder they stood on.
- Style Choice: While still practical in many ways, these days we wear hats primarily as a way to add a little pizzazz to an outfit.
History of the Hat
Since hats have been around since the dawn of time, you might be wondering about their history. So, it’s time for this ‘how to wear a hat’ guide to give you a little history lesson.
Hats are an ancient invention. The first depiction of one was traced back to Egypt in 3200 BCE. Like all garments, they have evolved significantly with the times.
In Ancient Egypt, they were both practical and a status symbol. Since most upper-class Egyptians had shaved heads, these head-pieces kept them cool under the hot Egyptian sun.
During the age of the Roman empire, brimless, felt, conical-shaped hats called pileus hats were common. Phrygian caps (felted hats with a distinct gnome-like quality) were worn by former slaves of the empire.
The style and shape of these caps continued to represent freedom, and they were worn during the French and American revolutions. The style of these hats might also suggest that they’re the great-great-great-grandfather of the hipster beanie, but that’s just our opinion.
While always signifying social status, the Middle Ages saw a rise in this concept. During this time period, laws were created that forced certain groups to wear hats.
In particular, the Jewish population in certain regions was required by law to identify themselves by wearing hats and various other garments.
The flat cap, which was introduced in the 1570s, wasn’t forced upon the wearer by law but it was used as a visual representation of the lower class well into the 20th century (remember Mary Poppins and the chimney sweepers).
The 19th century introduced hats that showed higher status, such as the ubiquitous top hat. The top hat was the umbrella term for a brimmed hat with a large top, and there were variations depending on the wearers’ location and occupation.
The Wellington, the D’Orsay, the Clerical, the Regent, and the Paris Beau were all versions of this iconic hat.
The top hat even influenced the style of hats worn by those in the armed forces. The Navy hat and the Continental hat also showcased the status of the wearer and ‘the higher the hat, the higher the status.’
The 19th century also brought with it the rise of the womenswear hat. Before this time period, women often wore scarves and bonnets as opposed to true milled hats. ‘Milled’ refers to a milliner, which is someone who makes hats.
By the end of the 19th century and throughout the 20th, hats became a staple of women’s fashion.
Modern-day hats are far less ornate than those of the past (except for the British fascinator, of course). The most popular style now is the baseball hat, which was invented in the mid-1800s as a way to keep the sun out of baseball players’ eyes while they were catching the ball.
Also, the beanie (aka toque) became popular during the mid-1900s and is still a staple today.
When to Wear a Hat
Besides knowing how to wear a hat, you must know when to wear a hat.
The time of year (the season) is the most important factor to consider when thinking about how to wear a hat. It will also determine which hat you choose. Mostly because, at its core, a hat is a practical item. However, the setting is also an important factor to consider.
In most cases, modern-day hats are considered casual. There are few dressy occasions when a hat is necessary or even appropriate (unless you’re a member of the Royal Family or Carrie Bradshaw attending her husband’s funeral).
How to Wear a Hat
When considering how to wear a hat, remember that adding one to an outfit is relatively easy. The only vital thing to consider is that it matches the style and energy of your outfit.
Make sure that your hat adds something to your look as opposed to taking something away. It should rarely be the key piece or highlight of your outfit—instead, it should be a thoughtful addition to a look you’ve already put together.
It’s also important to make sure the hat doesn’t alter your look, transforming it from an outfit into a costume. While it may seem like a good idea to toss that straw cowboy hat on with jeans, boots, and a flannel shirt, you might end up looking like an actual cowboy, instead of like a fashionista.
Also, when answering the question ‘how to wear a hat,’ it’s our professional duty to say that you must always wear your hat on the top of your head (sorry, we couldn’t help but make that joke).
8 Outfit Ideas With a Hat
When figuring out how to wear a hat, specifically a baseball cap, there are a few obvious ways.
- With athleisure
- Paired with jeans, a tee, and sneakers
- With a feminine slip dress
As you can see, there are many different outfits with baseball hats that you can choose from.
By adding a more masculine cap to an ultra-feminine outfit (in this case, a dress), you can transform a pretty look into a cool, laid-back outfit. This is one of our favorite ways to wear a hat.
The model pictured has her hair down, but if you have long hair, you can pull it back through the hole in the closure. Try adding a pair of sneakers with this ensemble to elevate it even further.
Wondering how to wear a bucket hat? Well here is your answer. The bucket hat can definitely emit NYC street-wear vibes, as we see here.
This Prada plaque bucket hat, paired with a silk ruched-sleeve bomber and jeans is a look that must be appreciated. It’s simple, hip, and a bit edgy. Also, the shared sheen of the jacket and hat add just the right touch of glam.
This is for all of you cold-climate ladies who are sick and tired of your everyday beanie.
Any question you may have regarding how to wear a hat, specifically a bucket hat, is answered in this picture.
Everything about this outfit screams luxury, including the leather and shearling lining. We only wish we could see her chosen footwear because if they’re matching leather, shearling-lined boots we might faint from fashion-based joy.
Of all the hats out there, the cowboy hat is the trickiest one to style without looking like, well, a cowboy. The above combination of a cowboy hat, feminine dress, and patterned hosiery allows this southern staple to rise to new levels.
When deciding how to wear a cowboy hat, make sure the other components of the outfit aren’t exclusively cowboy-esque—unless you have ivory cowboy boots like this gal.
However, swapping those boots out for knee-high, black suede boots will make an outfit like this even more accessible. The key is to channel Dolly Parton in The Best Little Whorehouse in Texas, not Burt Reynolds.
Another safe bet when wearing a cowboy hat is to bring it to the beach. Topping off your favorite bikini with a straw cowboy hat and some eclectic jewelry is a great way to rock this tough-to-wear style.
And if you’re wondering how to wear a hat with long hair, this is a perfect option.
This is the exact Acne beanie that I bought in Paris, and it’s so warm that it must only be donned under the chilliest of circumstances. This hat is also beautiful and incredibly well crafted.
By pairing it with contrasting colored coats, these women have transformed a practical beanie into something quite fabulous. If you’re wondering how to wear a hat in the coldest of climates, these gals have the answer.
A side note: see how simple their hair is? Washed and worn is the best option when you know you’ll be wearing a knit cap. Overdone curls under an ultra-hip hat is quite impractical, and won’t match the overall casual look.
And if you’re unsure how to wear a fitted hat, keep these tips in mind. When wearing a fitted hat, a simple hairdo is always best.
Styling a Panama hat is surprisingly easy. It’s basically the laid-back metropolitan cousin of the cowboy hat. Great shades, a pretty sundress, and your favorite handbag are all you need to make this outfit work.
So, when putting together your outfit, keep everything else pretty, and simple.
The beret, while a classic and inarguably beautiful hat, must be worn with care. If the backlash of Emily in Paris taught us anything, it’s that wearing a beret without thoughtful consideration can make you look a tad ridiculous under the scrutinous eyes of the fashion world.
Here’s my advice on how to wear this hat: pair it with something edgy, cool, monochromatic, and simple, as pictured on the chic-goddess above.
What Type of Hats Can You Get?
There are so many hats to choose from. In fact, the selection is almost endless. Below is a list of the most of-the-moment hats.
- Bucket hat
- Baseball cap
- Beanie (aka toque)
- Cowboy hat
- Boater hat
- Panama hat
- Beret
- Floppy sun hat
- Ascot cap
- Cloche hat
Okay, so the cloche hat is perhaps not ‘of the moment,’ but we love the cloche and its 1920s frivolity, so we decided to include it on our list anyway.
How to Choose the Best Hats
When choosing a hat it’s important to consider not only the price, quality, and material, but also your budget, your lifestyle, preferences, and limitations.
For instance, if you’re someone who enjoys a rotational wardrobe as opposed to one consisting of long-haul staple pieces, spending a significant amount of money on a hat may not be the best choice for you.
When it comes to quality, it’s also important to consider whether you have the time or inclination to care for a high-quality hat. Hats collect the oils from your head and hair products—meaning they need to be cleaned and cared for relatively regularly.
If you’re up to the task, it’s always better for the longevity of your item to buy a high-quality hat, and it’s much better for the environment to avoid fast fashion.
In terms of material, here’s where you have a little lee-way. You can get a high-quality cotton hat that’s also very easy to care for. Even merino wool can be machine-washed and hung to dry.
Plus, it’s important to consider your temperature threshold when purchasing a hat. I made this mistake once by purchasing a wool Acne toque that was so good at its job of keeping me warm, that it was unwearable for any length of time. So I keep it in a box in my closet just in case I ever travel to Nunavut.
How to Style a Hat
Adding a hat to an outfit is often an unnecessary but delightful treat. It also gives your outfit some extra dimension. Even though it’s a small accessory, a hat can shift the entire vibe of your look. And that’s why deciding how to wear a hat is so important.
For instance, by taking your prettiest slip dress and adding sneakers and a baseball hat, you’ve altered your look, transforming it from something girly and sweet to something more hip.
The addition of a bucket hat to any outfit adds an air of NYC streetwear style to your look, especially when it’s paired with anti-fit denim and a cropped puffer jacket.
What about the toque (aka the ‘winter beanie’)? Well, that’s easy—especially if you’re from a cold climate. Throw that hat on with anything between the months of October and March and you’ll look cool, be warm, and hide any hair-based malfunctions you may be experiencing that day.
Those are the easy hats to style. How to style a cowboy, Panama, or boater hat is a little bit trickier. However, much like the toque, or ‘winter beanie’ as our pals to the south call them, seasonality is key.
These three styles are, in my opinion, summer hats (with perhaps the exception of a felted Panama-style hat in the fall). There is little to no reason why—unless you’re an actual cowboy— you should be rocking a stetson cowboy hat in the winter.
The safest way to wear a cowboy, Panama, or boater hat is to be mindful of the material they’re made of. Our recommendation when deciding how to wear these bolder hats is to choose a lightweight, woven straw version (think Julia Roberts in Runaway Bride circa 1999).
Fashion Tips to Avoid With a Hat
If you’re wondering, what should I avoid when wearing a hat? That’s a good question. We’ve touched on a few of these fashion no-nos earlier in the article, but here’s a comprehensive list of ‘don’ts’ when styling a hat.
- Don’t allow your hat to take center stage or significantly alter the vibe of your look.
- Don’t forget about your hairdo. If your outing includes going indoors, know that you may have to remove your hat and you should consider the implications on your hairstyle.
- Don’t allow your hat to make your outfit into a costume unless it’s October 31st.
- Don’t attempt to wear a dress hat without some serious know-how. This is an extremely difficult look to pull off successfully (unless you’re Queen Elizabeth then this rule need-not-apply.)
- Don’t underestimate the bold statement certain styles of hats can make. Hats can be your friend or foe. So always be aware that your hat could betray you and your outfit. They’re the second-least trustworthy of all garments after the fanny pack.
- Don’t assume that one size fits all. If you’ve chosen a structured hat, make sure to measure your head. Like bodies, our heads come in all shapes and sizes, so be mindful of this when choosing your new accessory.
How to Take Care of a Hat
Once you know how to wear your hat, the next thing you need to know is how to care for your hat. This is dependent on the type of hat you’re caring for since they all have specific needs. So check out the expert tips below.
- Consider the material: If your hat is knit, be sure to follow the wash-and-care instructions suggested by the manufacturer. A cashmere toque will require different care than a merino wool cap or cotton hat, and so on.
- Buy hat boxes: If you own a more structured hat, like a boater, Panama, or cowboy hat, we suggest investing in some hat boxes. Not only do they make pretty home decor, but they’ll also keep your hat safe from bends and breaks which can ruin your treasure.
- Travel safely: If you’re traveling with a hat, we suggest wearing it while you’re on route as opposed to shoving it in your suitcase. Crushing a structured hat, with perhaps the exception of a wide-brimmed straw cowboy hat, can permanently destroy the piece.
Best Places to Buy a Hat
If you’re looking for a packable, well-made and affordable hat, hatattack.com has a wide range of options. From wide-brimmed sun hats to felted Panama hats and pretty wool berets, Hat Attack has a lot of great hats to choose from.
Founded over 40 years ago in Manhattan by a husband and wife team, the excellent quality and reasonable prices of these pieces make Hat Attack a wonderful hat retailer.
If you’re looking for something cool, like a toque or an elevated baseball cap, rag & bone has an entire accessories department dedicated to headwear. Many of their products have different color, content, and style options, so you can find exactly what you’re looking for to complete your look.
If you’re in the market for a true treasure, steeped in classic millinery, look no further than Borsalino. Founded in 1857 by Giuseppe Borsalino, this Milan millinery crafts some of the most exquisite hats in the world.
The quality and history of these hats make them investment pieces that can be handed down through the generations. In one of the most famous scenes from one of the most famous movies of all time (Casablanca), Ingrid Bergman and Humphrey Bogart are wearing Borsalinos.
Final Thoughts
Ultimately, a hat is a form of self-expression, like all garments and accessories. It’s something to be cautious of, but when executed properly, the addition of a hat can add a lot to an outfit.
It has the ability to transform a look, however, it’s important to make sure that it’s transforming your outfit in a positive way.
By referring to this style guide, you should be able to put together a trendy outfit and avoid the fashion faux pas we mentioned above.
And if your clothing and shoe collections are complete (if they ever can be), then adding some hats into the mix is a great way to change things up.
Plus, with the addition of hats, you’ll have even more stylish outfit options to choose from. How exciting is that!
Wondering how to style different accessories? We’ve got you covered:
