Whether you’re wearing a classic baseball cap or wearing a dapper fedora, hats are the perfect topper (no pun intended) to any outfit. Read on for our complete guide on how to wear a hat for men.
Types of Hats for Men
The Dad Cap / Baseball Cap
Like dad jeans and polo shirts, we’re a little confused as to why this norm-core trend has popped up, but as of recently, everyone from Kanye West to Drake has been rocking the dad hat. Dad hats aren’t like your regular baseball cap. Generally, they’re unstructured (so no extra padding in the front, similar to a fitted cap), made of cotton, and are typically all one colour.
If you’re going to wear a dad hat, wear it with something equally as laid back, chinos or black denim are a great option. Staple jackets and motif sweatshirts are a great topper. Lastly, keep your look consistently laid back with a trainer.
The Panama Hat
When opting for Panama hat, keep your look classic, minimal and neutral. We prefer pairing the hat with a t-shirt, slim jean and a tanned smart shoe. If the weather is a bit cooler, then throw on an easy-going buttoned shirt to give your look a bit of persona.
Since the snapback is a laid back style of hat, avoid pairing it with more formal options like a sports coat or blazer. We recommend pairing it with a simple t-shirt or buttoned shirt (and some wicked shades!) for a great, laid-back summer feel.
The Fitted Cap
Like the snapback, Fitted caps are hugely popularised by rappers and sports players and can be a tough trend to pull off. Too often these caps are favoured by reality TV shows and truckers. To avoid pulling off a fitted cap without looking like you wear seven chains at all time, try picking a hat that is more subdued in colour.
We recommend keeping the brim forwards, rather than sideways or backwards. One polarising debate about fitted caps is the stickers. Some people are religious about their cap stickers, and think that keeping your stickers on your cap is a great way to show off your style. We recommend taking them off – anyone worth impressing (ladies, employers, etc.) probably won’t notice if you have your stickers on or if you don’t.
The Flat Cap / Derby Cap
Originally a hat favoured by English hunters and newspaper boys, the flat cap is a great way to update any smart-casual look. Think of it as a spruced-up version of the baseball cap -with a touch of heritage.
The Trilby Hat
In essence, a Trilby hat, or the Frank Sinatra hat is similar to a fedora, but the brim curls up in the back and down in the front. It’s a true gentleman’s cap – it’s guaranteed to polish any outfit!
The beanie is the perfect winter accessory. Not only does it keep your head warm, but it’s a great suave, casual topper for any outfit. Pick a light weight knit for the warmer days, or a heavier weave for colder ones. One of the best parts of a beanie is that they match everything, toss one on with jeans and a t-shirt to run errands, or pair with a more formal look to add a little edge.
You can wear a beanie several ways. Keep it unfolded and slip it on just behind your ears for a casual, more bohemian feel. For a more street look, fold up the brim once or twice and wear like a toque.
One thing to remember; although beanies are a great staple hat, they can ruin any man’s hair. If you’re removing your beanie inside, take a pit stop in the restroom to double check to see if your hair is in place. On the flipside, if the weather is treacherous outside, slip a beanie on over your hair to protect any styling!
How to Wear a Staple Hat
Now we’ve covered the basics, it’s time to clue yourself up on the wardrobe essentials. From the fedora to the bucket hat, here’s how to wear the staple hats.
How to Wear a Homburg Hat
The Homburg hat is a stylish hat option that’s been around for quite some time now. The round brim felt hat has been seen on the most distinguished men for decades, similar in shape to a Trilby or Pork Pie, but with a wider brim. The Homburg has been picked up by everyone from The Godfather to Snoop Dogg, so wear with appropriate swagger.
How to Wear: While it can look incredibly stylish with a suit, it’s best worn with some smart casual or casual tailoring pieces.
How to Wear a Fedora
Fedoras have a bad rap, over the past decade, they’ve been pulled off poorly by rock stars and golfers alike. But behold, you can pull off a fedora well!
How to Wear: Pair a fedora with a suit or blazer to instantly up your dapper factor. Being more of a winter wardrobe addition, play around with layers consistently through your outfit. Pick a fedora with a wider brim to add a masculine edge to the topper.
How to Wear a Cap
The flat cap hasn’t always been favoured by the fashion folk. Even though the cap, favoured traditionally by huntsmen and newspaper boys, it’s extremely stylish. If you’re unsure on how to wear a cap
and have a go with it worn incorrectly, it can look quite ridiculous. When worn correctly, however, it can be a seriously successful style statement.
We recommend finding one that fits well. There’s nothing worse than a floppy or top-tight flat cap. Find a hat that doesn’t have too much excess fabric along the flat top. It should not be ballooning, but rather just fall casually. The cap itself should fit just above your ears.
How to Wear: Wear it with modern clothes to spruce up your more laid-back appearance. Avoid wearing it with more dated clothing, like bow-ties or suspenders. This can make the outfit look a little too stuffy if not thought out carefully!
How to Wear a Bucket Hat
Bucket hats aren’t just for fishermen, we promise! Even though the style is a little out there, it’s surprisingly a super laid-back trend that’s easy to pull off. From Gilligan’s Island to the legendary 90’s rappers, bucket hats have proved to be a trend that’s here to stay.
No matter your hairstyle, bucket hats are a viable option for day to day wear. The longer brim of bucket hats pair well with men with longer tresses, and they frame the face well for those with a close cut. Because bucket hats are already a bold option, it’s perfectly normal to pick a bucket hat in a bold pattern like a check, stripe, or graphic design. The number of ways to wear a bucket hat is limitless.
How to Wear: Pair it with more formal street wear pieces or an Oxford shirt and you’re ready to hit wherever the day takes you. We do recommend streamlining your top half to balance out a more laid-back nature of the hat.
Hats to Wear with Suits
At the end of the day, you can wear any kind of hat with a suit, as long as you wear it with confidence! A beanie looks great with a suit if you’re running out of the office and into the colder weather. Avoid a drooping beanie, as will detract from the sharpness of your suit.
If you’re feeling daring, wear a baseball cap with a suit! This look is tougher to pull off, as it can quickly look like high school dance attire rather than a dapper outfit. Make sure the hat you choose is minimalistic in colour, and doesn’t distract too much from the suit’s lines.
How to Choose the Right Hat for Your Face Shape
Picking a hat for your face shape is similar to picking a pair of sunglasses. Always remember to consider proportions. Larger hats look better on men with larger heads, while larger hats on men with smaller heads can sometimes look overwhelming so it’s very important to consider both head size and men’s face shapes before purchasing.
Tips on Choosing the Right Hat for Your Face Shape
- Hats with a flat brim will draw in more attention to your face by acting as a frame. If your cheeks are a little rounder, a tight fitting baseball cap can accentuate that feature. Try out a hat with a brim to make your cheeks look a little less round.
- Angular hats work well for those with a rounder face, so opt for a hat with a high crown, or a just slant your hat forward.
- If you have a square face, opt for a hat with a floppier fit, like a bowler, or a more organic fitting fedora.
- If you have a face that is longer than it is wide (so closer to an oval than a circle), opt for a hat with a flat brim. Hats like a wide-brim Panama or a flat top will compliment your face, while a hat with a short brim will elongate it.
For a more accurate hat fit, measure around your head with a measuring tape. Hold the measuring tape just above where your hat would sit, so typically right above your ears. Feel free to head into your local hat shop to try a few sizes!
Your Quick Guide on How to Wear a Hat
- Confidence is key. A shrinking violet in a fabulous fedora just won’t cut it
- Never buy a hat online unless you’re familiar with the style and brand
- If your hat it just a little too big, you can stretch it over time
- It’s important to consider face shape when choosing a hat; what works for one person, could be terrible on another
- Be sure to remove the sticker from your snap back.
- Look after your hats, especially when storing them. The well looked after, the longer they last.
And On That Note
Hats tend to be more of a statement piece than a subtle accessory, one of the key tips when wearing a hat is to wear it with confidence. Flip a hat on and you’re instantly transformed into a mysterious Gregory Peck or a street-savvy Kanye West.
Maybe you want to instantly add a whole dose of personality to any outfit? You wear a hat to keep your head warm on a chilly day? Or maybe you’re wearing a hat to cover a bad hair day? Either way, hats are a great way to take your style game from 0 to 100 (as so said by our Editors). With this handy list, you’re sure to up your style cred.
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