4 Tips For Styling A Trucker Hat

October 23, 2023

How can you showcase your unique style with a simple trucker hat? We’re sharing four ways to add that “wow” factor to your wardrobe with this fun and functional accessory.

Trucker hats still rock, so here are some ways you can wear a trucker hat

Trucker hats have been around for a while now. This cap with a wide brim, mesh backing, and foam front is a go-to accessory for everyone from farmers to fashionistas.

What started out as promotional freebies for working-class truckers in the 1970s became a stylish accessory in the early 2000s and grew in popularity thanks to celebrities like Ashton Kutcher, Pharrell Williams, and Paris Hilton.

The trend has endured because these hats are versatile and varied. They’re cool and casual but can elevate your style as well.

If you’ve hit a wall when it comes to what to wear with your favorite trucker hat, we can help. To start with, you just need the perfect trucker hat. There’s a world of options out there when it comes to finalizing your look, but for now, we’ll talk about four. Try one or try them all.

There’s no limit to how you can level up your look with a trucker hat the next time you head out.

1. Kick it up country style

First, we’d like to tip our hats to the humble roots of the trucker hat. As alluded to above, companies often gave away branded caps at truck stops to promote their products.

While many truck drivers were probably not worried about what to wear, their rugged and road-worn appearance is one of the effortless looks that others have since tried to emulate.

There’s a range of outfits that could be considered blue-collar, country, or western. Whatever you want to call this style, denim is definitely going to be involved.

The clothes

Yes, the key to the country style – and also, quite often, a country song – is a good ol’ pair of blue jeans. They’re almost as essential as an old truck, a cold beer, and a dog.

Most trucker hats are worn forward facing like this actual trucker with trucker hatSo go ahead and throw on your favorite pair of jeans. Rips and holes are not required but will give the outfit an extra air of authenticity. Alternatively, a brand new pair of dark blue or black jeans can class it up a bit.

If you tossed your last flannel shirt in the trash around Y2K, then it’s time to hit a thrift store or literally any department store. Flannel shirts are also perfect for the colder weather that comes with Fall.

Grab a comfy tee or tank top and pair it with your new-found flannel. Extra points if your t-shirt has a Dolly Parton quote or a pun like, “I beg your Parton.” Remember, a little sass goes a long way.

Think about coordinating colors and not going too neon or bright. Subdued hues work well if you’re going for the rugged look.

Wearing a denim jacket with wool or fleece lining is one option, or you can complete the ensemble with an oversized corduroy coat.

Whether you’re on your way to do a little boot-scootin’ and whiskey-shootin’ or just hanging out with old friends, this casual look lets you feel comfortable and confident.

The shoes

One way to work it is with work boots. Wearing something sturdy shows that you’re not messing around. It lends the look some strength. Plus, a solid shoe means you can pitch in and help out.

You could also go full cowboy and dust off your cowboy boots. A big part of pulling off any outfit is confidence, so just be sure it aligns with your personal style.

Though the overall look is casual, it’s not the time to incorporate Crocs or flops. Save that for one of the following looks.

The hair

Wear your hat facing forward for sun protection and to complete this classic trucker hat style.

As far as what to do with your ‘do, there are a few options. If you have long hair, you can put it back in a ponytail and either thread it through the hole in the back or wear it low enough to pass under.

There’s something about braids or pigtails at the nape of the neck that can bring a bit of country charm to this look. Maybe it’s because it reminds us a little of Dorothy and how there’s no place like home.

The accessories

Aviator-style glasses work with almost any outfit and when wearing trucker hats. Tortoise shell and neutral tones are also appropriate with this kind of country casual wear.

You can coordinate the color of your belt with the boot you’re wearing, though there’s no hard and fast rule that it has to be exactly the same.

In general, you don’t want to over-accessorize when you’re kickin’ it country style. If you have a signature chain or simple necklace, that might be all you need.

If you wear earrings, this might be the time to keep it minimalistic or just show a little sparkle. Again, it’s ultimately up to you how you make it unique, but if you are dressing it up or down, just be consistent across the entire outfit.

2. Beach vibes

When Summer comes around, there are several different styles you can try with trucker hats. When it’s hot outside, a trucker hat can keep you looking and feeling cool.

‘Tis the season for bold bright colors and a good excuse to experiment with new patterns. Wahine and kane (women and men) can get wild! Anything goes when you’re near the water, so go ahead and wear an outfit that might be considered NSFW.

double portion supply white hot pink foam trucker hat

The clothes

How about trying a hot pink trucker hat that picks up on the pinks in your bikini? Then all you need is some cutoff jean shorts and a loose-fitting linen or cotton button-up shirt. (Actually, using those buttons is, of course, optional).

If you’re hanging at the beach, maybe try a trucker hat with colorful camo to catch the eye of your crush and make those boring board shorts a bit more exciting.

Trucker hats paired with t-shirts and shorts are a staple and allow you to make your personal mark with whatever brands or type of fit you favor.

A plain trucker hat is perfectly fine, but you can also say a bit about yourself with a logo or graphic of your choice. What’s more friendly than a flowery Aloha on a foam front? The best trucker hats help you express yourself.

The shoes

No shirt? No shoes? No problem. This is when barely-there wear is A-OK. Of course, though it’s great to be grounded, most of us want something between our feet and the floor. For that, we have flip-flops or anything else you can easily slip on your feet.

The hair

Whether you have short hair or long locks, you can wear a trucker hat to have a carefree, no frills, hakuna matata hair day. Pull it back in a ponytail to completely keep it out of the way, or frame your face with a few strands. Low pigtails and loose braids also give good beach vibes.

You can wear it facing forward for maximum shade or turn it around for tossing the frisbee or a game of beach volleyball. Dig it.

The accessories

While a forward-facing trucker hat will help shield your eyes, direct sunlight can be intense when you’re at the beach. It all works out, though, because sunglasses are essential to any summertime trucker hat outfit.

To keep it classic, wear a trucker hat with some wayfarers or go big with oversized sunnies that make a statement. Before you crank the tunes up and put the top down, pop that trucker hat on your head and head to the beach in style.

3. Play around with a punk style

Trucker hats may not be the first accessory that comes to mind when someone says “punk,” but what’s more punk than going against conventions and defying expectations?

From goth to glam to skate to pop, a whole bunch of subcategories and subcultures have adopted this style we often associate with a “stick it to the man” attitude. Though this crowd is frequently seen in leather and denim, the styling rules are that there are no rules.

The clothes

A worn-in tee or torn up tank top with the name of your favorite band (whether it be store-bought or written with a Sharpie) should be all you need to start. Then put on a pair of well-worn jeans or a plaid skirt with a studded belt.

The shoes

Doc Martens or any kind of steel-toed or sturdy boot can complement this bold choice of the trucker hat. Chucks, if styled correctly, could also work.

The hair

Sporting a mohawk, multi-colored hair, or a shaved head will surely set you apart from the crowd.

Guy in trucker hat with piercingsYou can also work with a more natural style. Try putting in a little product and play around to see how your hat fits in.

The accessories

Trucker hats put a fun twist on the classic punk look. You can also layer on leather or denim jackets with patches, pins, paint, or chains. You name it, it’s not off-limits.

While some say less is more, “more is more” should be your mantra here. Add a little metal anywhere across your ensemble, including your trucker hat, and hey, even your body. Piercings are pivotal to the punk aesthetic, after all.

A choker necklace could also be a stylish addition to this trucker hat look.

4. Sporty and casual look

The trucker hat is a cap for any occasion. You can don your hat with casual clothing like athleisure wear and other kinds of sportswear.

Over the last several years, it’s become quite commonplace for workout clothes to be worn just about everywhere. So whether you’re actually hitting the gym, hiking with friends, or just heading to brunch, trucker hats are here for you.

The perfect trucker hat to complete any casual look is hands-down Double Portion Supply’s All Solid White Foam Trucker Hat. This clean cap goes with any outfit!

If you’re not sure how to style trucker hats with workout clothes, keep reading.

The clothes

You can wear a trucker hat with leggings and a fitted tee or oversized sweatpants and an old tank top. Something about having that hat on says, yeah, I meant to do that.

It’s another great opportunity to experiment with fun patterns that showcase your personality and spice up your outfit. A wild logo on your trucker hat will also do the trick.

Alternatively, you can go the classy and clean route while wearing athleisure.

If you want to dress it up a bit, go for a monochromatic ensemble. Wearing high-quality fabrics in the same color family from head to toe creates a classic and clean aesthetic. Try all black, a dark green, or whites and creams.

The shoes

Sneakers reign supreme when we’re talking casual clothing and trucker hats.

You’ll want to make sure your kicks come in the same hue as the rest of your outfit if you’re keeping it classic and more upscale. It helps create an elongated silhouette.

The hair

The right fit of your hat will help preserve your hair how you want it. A tighter fit helps tame your mane, like a slicked-back bun poking through the back of your hat. A looser fit of your hat allows for voluminous curls or wild waves you don’t want to flatten down.

The accessories

If you’re striving for that stylish and slightly upscale look, throw a sweater around your shoulders. Otherwise, any sweatshirt should suffice.

woman in black puffer jacket and blue design trucker hatIf it’s cold out, warm up with a puffer jacket. Then a fanny pack, cross-body bag, or backpack will be all you need to be on your way.

It seems there’s no end in sight for the trucker hat trend.

The trucker cap has come a long way from when it was primarily worn by truckers or farmers. Everyone from celebrities to the guy on the corner asking for cash can rock trucker hats.

As you can see, there are various ways you can incorporate trucker hats into your wardrobe.

Whether you’re dressed to the nines or barely keeping on that bikini, you can do just like that Joe Cocker song says…you can leave your hat on.

Keep Reading: What Are Dad Hats, And Why Are They So Popular?

Double Portion Supply is the largest snapback superstore in Hawaii. Since 2001, we’ve helped clients across the United States make their creative vision a reality. From low-profile dad hats to ANXD brand apparel, we carry everything you need to keep your own brand stocked. Plus, our custom services extend to T-shirt printing, so you stay fresh from head to toe. Get all the latest information by following us on TwitterFacebookInstagram, and Pinterest.

Aaron Graziano