How to Wear a Trucker Hat

Co-authored by wikiHow Staff

Last Updated: March 29, 2019

Trucker hats are unique accessories that became popular in the 1970’s. They’re characterized by their mesh paneling, high dome area, flat bill, and adjustable back, and have gone in and out of style over the years. If you really like trucker hats but just aren’t sure how to wear them, you have many different options. Choose a hat with a color and shape that work for you. Then decide which hat position looks best with your own personal style, and finish putting together your outfit accordingly.

Part 1

Part 1 of 3:

Choosing a Hat

1
Measure the circumference of your head. While most trucker hats are advertised as one-size-fits-all because they’re snapbacks, they typically only allow for about 1.5 inches (3.8 cm) of adjustability. Use cloth measuring tape to measure around the widest part of your head.^{[1]
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- If your head doesn’t fall between 22 inches (56 cm) and 23.5 inches (60 cm), then you may need to custom order something bigger or smaller.
2
Go bold with bright colors. If you like to push stylistic boundaries and stand out, consider getting a trucker hat that has one or more bright colors, such as red, purple, or teal. While wearing a hat this bold isn’t for everyone, it’ll fit well with colorful clothing and eye-catching accessories.^{[2]
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3
Get a trucker hat with a less prominent dome to fly under the radar. While trucker hats are known for their big, flat bills, mesh material, and tall dome area, you can blend into the crowd a little more if one of these characteristics is toned down. Try a few different trucker hats on and choose one that doesn’t sit quite as high above your head as others do.^{[3]
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4
Bling out your trucker hat to get the gangster look. Bedazzling is a big part of gangster style, whether you’ve got diamonds on your necklace or on the surface of your flat bill. Get a hat that’s decked out in sparkle if you’re hoping to display that gangster-like flashiness.^{[4]
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- If you’re creative, you can also purchase a plain trucker hat and bedazzle it yourself.
5
Try a camouflage trucker hat if you’re outdoorsy. If you want a trucker hat more for utility than style, then a camouflage design might be right for you. Wearing a camo hat can help you blend into nature while hunting or bird watching. You can also get a camo hat if you simply like the country style.^{[5]
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- Camo trucker hats come in many different colors, including brown, dark green, tan, and black.
6
Design and order a custom trucker hat. If you are creative and/or have a brand or company that you’d like to market for, design and order a hat online. This is relatively inexpensive to do, and can help spread the word about something you love.^{[6]
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Part 2

Part 2 of 3:

Positioning the Hat

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Wear it naturally facing forward for a smart, casual look. The classic way to wear a trucker hat is facing forward and fitted to the head. This is an easy, comfortable position that can give off an intelligent, laid-back vibe when worn with the right outfit.^{[7]
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- Try wearing black fitted pants, a white v-neck, and a jean jacket with your forward-facing trucker hat to achieve this look.
2
Wear it backwards and pointed down to give off a cool vibe. If you wear your hat straight backwards, it might look a little retro-gone-wrong. Avoid this fashion faux-pas and go for a much cooler look by placing the back of the hat just above your hairline and allowing the bill to point downward behind you.^{[8]
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3
Pull the bill up to get a bold, trendy look. If you like to be more daring with your fashion choices, put your hat on so that it’s facing forward with the bill coming out from your upper forehead horizontally. Then, lift the bill up so that it moves from your forehead to just past your hairline and is about halfway between horizontal and vertical. This makes for a fashionable European-inspired look.^{[9]
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4
Avoid wearing your hat sideways. While wearing billed hats sideways was somewhat acceptable during the 1990’s, it’s no longer a trend. Go with a forward-facing or rear-facing position instead if you want to be stylish.^{[10]
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Part 3

Part 3 of 3:

Finishing the Outfit

1
Go casual with a basic t-shirt and jeans. If you prefer to wear your trucker hat facing forward in a natural, fitted position, throw on a basic v-neck and a pair of comfy jeans to go with it. This look is comfortable, simple, and stylish.^{[11]
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2
Pair a neutral hat with a fitted shirt to dress it up. If you have a trucker hat that’s a dark neutral color, such as black, you can accomplish a classier look with just one minor adjustment. Upgrade from a tee to a classic long-sleeve button-up to take your outfit up a notch.^{[12]
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3
Stick with simple solids if you’re wearing it backwards. If you wear your trucker hat backwards, you may sometimes come off to others as slightly shallow. Wear some jeans and a solid-colored shirt with your backward-facing hat to appear more humble and thoughtful.^{[13]
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4
Show off your urban style with a sweater and some trousers. For a streetwear look, wear your trucker hat facing forward but pushed down onto your head a little more than normal so that it looks more fitted. Put on a name brand shirt or sweater, wide-legged work trousers, and a casual sneaker.^{[14]
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Community Q&A

Question

Why would I leave the price tag on the hat?

Nicky Ruby

Community Answer

Many fake copies of popular brands are available these days, so the obvious reason might be that it looks authentic if you kept the price tag. Also, it gives the wearer a feeling that the hat is still new and fresh. But it's totally not necessary to leave the price tag on the hat.