Last Updated: May 25, 2017 | This Article May Contain Affiliate Links
how to wear a hat

10 Tips On How To Wear A Hat The RIGHT Way To Avoid Embarrassment

Hats provide a fresh new look to your everyday outfits.

However, it can make or break the outfit you’re wearing depending on what you pair it with.

Don’t be caught mixing the wrong hats or wearing the hat incorrectly; follow these tips to ensure your style remains sexy and cool.

how to find your perfect hat

1. Needs To Be Paired Properly

All hats have their place, mix the wrong outfit and hat though, and you’ll end up looking like a style rookie.

Don’t even think about pairing a baseball cap with boat shorts or a fedora with jeans.

Not only will you look out of place, you also leave the impression that you have no idea how to dress.  This can lead to the impression to others that you are sloppy and not put together.

If you’re unfamiliar with different hat styles, go shopping and have a stylist put together a whole outfit for you.

This is a great way to find the perfect hat and outfit to match.

2. Confidence Is Key

Believe it or not, the most attractive thing about you men isn’t your face; it’s your confidence.

Confidence gives you a glow and reassures everyone surrounding you that style is your game and you feel good about it.

Nothing is sexier than a confident man.

If you don’t feel super confident about your style choices, hats included, your outfit might not go well together.  There are many ways to check to see if your outfit hits all the style points.

Look at magazines, store ads, or websites to find similar outfits.

When shopping for new clothes, ask the sales associates what hats they would recommend with the outfit you pick out.

Ensuring that you feel good in your ensemble will give you the confidence you need to rock that new hat.

3. It’s An Accessory To The Perfect Outfit

If you ever are unsure about your hat, maybe it’s your outfit that needs some redoing.

The great thing about hats is when you dress good, the hat looks good.  An outfit choice that is sure to get you style points is when you pair your hat with some dark denim and Chelsea boots.

Roll or cuff your jeans to hit right at the ankle to touch the top of your Chelsea boots.

The hat will not only complement the boots, but it will be the perfect cherry on top to your outfit.  A summer option would be to wear some chino shorts and a button down.

There’s a multitude of hat styles you can choose that would look good with those outfits during the summer and winter.  Stick to hats that go well with your shoes, usually that’s a neutral color hat with a small pop of color when going for a bolder look.

hats for men

4. Pinterest Isn’t Just For The Ladies

Not familiar with Pinterest?

Time to add another social media app to your phone.

Pinterest may seem like it’s for women, but that can’t be further from the truth!  If you are ever unsure about your outfit choice, jump on Pinterest and look at the men’s style section.

You are bound to find multiple perfect style icons that you can copy.  Pinterest is especially helpful with hat pairings.

If you are new to hats, look through Pinterest.  There are hundreds of thousands of photos on there that can show great hat pairing examples.

Through these photos you can also find links of where to go to buy the items shown in the photos.

If you find an outfit you like, follow the link to purchase all the pieces.

Buying an already put together outfit will make you feel confident when it comes.

5. Buying Online Can Be Tricky – Amazon, Nordstrom, Huckberry, and Mr. Porter All Offer A Great Selections

Online retailers are especially great if you live in a smaller town or far from a city where hat stores are incredibly hard to find.

Thanks to the Internet, you don’t have any excuse to not shop for the perfect hat!

This is especially great for everyone who lives far from a major city with the biggest retailers.

While shopping online can lead to pieces of clothing that look awful on you, or clothing that just doesn’t fit, there’s a lot of high end sites that can get you dressed to impress.

These sites have easy shipping and return policies so you can shop without fear.

Amazon is a great place to start.

Amazon has thousands of different brands and styles of hats to browse through.  They also have hats in any price range.

Need a budget hat?

Amazon is sure to have the perfect hat for you.  Before buying, look through the reviews.  Lots of individuals on Amazon will take pictures of the product and even post photos of them wearing it!

This can help a ton in which hat to choose.

If you can spend a little more, Nordstrom and Mr. Porter are great options.  Nordstrom’s free shipping and free returns makes it especially easy if you live far from a city.  You can purchase the perfect hat and if for some reason it doesn’t work out, the return is quick and painless!

Mr. Porter also has a great selection of all types of hats.

They are high quality and have tons of styles to keep you looking put together.

Quick Links:

6. Baseball Caps For Casual Wear

Men in baseball caps, is there anything better?

Baseball caps are downright sexy in multiple situations.  From country boys, baseball players, and to your everyday man, anyone can feel good rocking a baseball cap.

While this is certainly a much more casual hat style, it can still bring your outfit from dreary to sexy.  Pair it with dark or light fitted denim and a casual tee and you are good to go!

One thing to remember is that baseball caps are not for everywhere.

Throw one on when going to a sporting event, use them for the weekend, and for outings with your family or kids.

Don’t be the embarrassment at a holiday party or fancy night out when you are sporting a baseball cap.

And about those stickers…

Come on guys, if the stickers were meant to stay on the hat, they wouldn’t have made it a sticker!

Take the stickers off.

You wouldn’t leave your tag hanging out of your jeans, would you?

No, so don’t leave the stickers on your hat bill.  They are not meant to be there past the day you buy it off the shelves.

newsboy cap

7. Newsboy Cap

Newsboy caps offer a great balance between both casual and formal wear.  Typically paired with a sophisticated smart casual wear, newsboy caps are a great addition to any ensemble.

If you are looking to up your style for weekends without relying on your trusty baseball cap, these are a great alternative.

Their largely conservative appearance take a stark contrast of the panama hat that is finding its way into the hands of hipsters throughout Williamsburg and other creative urban areas.

8. Be Like Frank And Know When To Wear A Fedora

Gone are the days of the thin mustache and pinstriped fedora often seen on gangsters in the 1900’s.

Fedoras have been reinvented into a great dressy hat that looks good on anyone.

Fedoras are sold at all of your top stores and are easy to find.  Nervous to take the fedora plunge?  Stick to a neutral color that matches your pants to ensure seamless style.

With buying a fedora, comes the fedora responsibility.

You should know that fedoras are trusted to be worn on a dressy occasion.  Now, that doesn’t mean you can only wear them at a wedding or church, they are perfect for summer too!

Just make sure that when you are wearing your fedora that you pair it with some light dress pants or a blazer.

straw hats

9. Straw Hats Are Perfect Summer Wear

Think of the country when you think of straw hats?

Erase that image out of your mind!

Straw hats are in style and coming to all stores near you.  This is the perfect hat for dressing up or dressing down.

Straw hats come in fancier styles for a day on the yacht and casual styles for a day at the pool.

This is the hat of the summer.

Everyone needs a straw hat.

Not only will it protect you from getting burned out in the summer sun’s rays, it is also super light and airy allowing you to wear a hat without embarrassing sweat.  Need another reason to wear your summer chinos and button down tee?

Grab your straw hat!

Create the perfect summer boating look by pairing bold colored chinos with a neutral tee and a dressy style straw hat.

Going to a beach party instead?

Wear a casual straw hat with your swim trunks and tank to keep cool.

10. Snow Caps and Beanies

Alright snow men; this last one is for you.

Love your furry snow caps and your beanies?

They are the perfect hats… for winter!  The great thing about beanies is that they can be paired with jeans, sweats, or snow gear.  They are a great staple for those days that your hair might not lay right, or when you are too tired to do it.  They are also great for keeping your hair from getting rained or snowed on.  If you are going on a cabin trip or a skiing trip, grab those snow caps!

Snow caps look awesome for winter bonfires, Christmas tree shopping, and snowboarding.

This should go without saying, but we are saying it just in case!

Don’t wear your beanies and snow caps in the summer.

They are meant for winter months!

Keep your head warm from Labor Day to Easter, and then put them into winter storage.  Wearing them during the summer can make you look confused and out of style.

Shawn Burns | @toolsofmen

Hi, I'm Shawn! A beard and shave enthusiast! I am an aspiring writer that wants to give guys great tips on how to pick up better grooming habits!From beard oil to using a double edge safety razor (yes I do get rid of my beard every now and again), I wanted to create this site where readers can get great information about men's grooming.

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