hats Never Wear On A First Date

5 Hats Men Should Never Wear On A First Date

Published: 03/03/2021

Since the UK government rolled out its new plan for lifting lockdown restrictions later in the year, everyone’s been looking forward to socialising in person again. Among coffee mornings and evenings down the pub with pals, arguably one of the most exciting parts of lockdown lifting has got to be the world of dating reopening! Although it’s too early to go on any romantic outing right now, there’s nothing wrong with planning ahead. As well as getting a fresh trim down the barbers, a wardrobe refresh is a great way to feel more confident and settle any pre-date nerves - and a new set of men’s clothes can be bought well in advance.

Brand new jeans and a nice shirt are a great starting point, but if you really want to impress your date you’ll need to accessorise. Men's hats are a brilliant way to top off your first date outfit (literally!). But a word of caution, when it comes to what to wear on a first date, there are good decisions and very, very bad decisions. To help you avoid making a first date fashion faux pas, we’ve judged the five worst hats you could possibly wear on the big day. From the goofy to the downright garish, you should probably leave these on the hat rack if you’re looking for that all-important second date!

Fedora or Trilby


Alright guys, let’s be real: you knew these two mens hats would top off the list! What’s the difference between a trilby and a fedora? They have similar shapes, but a fedora has a wider brim and a hat band, while a trilby normally has a short brim with a tight up turn at the back. Now that you’ve learned that information, forget it! There’s no excuse for wearing either of these hats on a first date... unless you’re deliberately going for the Olly Murs circa 2011 look.

Fedoras and trilbies ruled mens hats for almost half a century, first popping up in the 1920s and finally taking their bow in the late fifties. These hats were a more fashionable alternative to the bowler hats and top hats of the Victorian age, and paired well with suits. 

Fedoras had been out of style for a full half-century before they saw a bit of a resurgence. Bringing fashion statements back from the dead is a fairly regular occurrence, but the fedora/trilby revival ended up being the final nail in the coffin for these hats. Rather than dressing up in a full, well fitted suit, modern formal hat wearers paired them with ragged jeans and graphic t-shirts - not the best look! 

Trilbies and fedoras became so associated with fashion horror stories that they’re irreversibly tainted. Even if you come dressed to the nines in a suit, these hats rarely work on younger guys. The only man who could pull off wearing a trilby after the sixties ended was Leonard Cohen and, unfortunately, you’re not Leonard Cohen!

Literally Any Novelty Hat

novelty hats

This is another kind of hat that’s a definite ‘no’ when you’re thinking about what to wear on a first date. As a general rule of thumb, if you can find it in a fancy dress shop, you should probably leave it there! We’re talking everything from spangly cowboy hats and hats shaped like fruit, to beer hats and anything adorned with ears, horns or antlers - the list goes on. 

Okay, so Woody may have found love with Bo Peep while rocking the cowboy hat, but as the “rootinest, tootinest cowboy in the wild, wild west”, he could certainly pull off this look more than most. But it’s not just the out-there fancy dress hats that fall under this list - we’re placing bowler hats and top hats in the novelty hat category, too. Sorry steampunk fans!

The Bucket Hat

bucket hat

As the 2020s get into full gear, expect the thirty-year nostalgia cycle to move from the eighties to the nineties. There are many things to love about this decade, but fashion isn’t among them. Apart from tie-dye T-shirts and oversized JENCO jeans, one fashion trend that should remain in the past is the bucket hat.

Also known as the Kangol Hat, this headgear blew up in the nineties. From Stone Roses fans to West Coast hip-hop stars, the bucket hat spanned culture and geography. It epitomised the hopeful dream of the nineties: that things could only get better, just like D:REAM promised us. But D:REAM broke up, and it’s time to break up with the bucket hat, too. Or, as Gen Z would say: “Thank u, next!” 

The floppy brim and loose crown mean that a bucket hat always looks like it’s melting. Add to that a focus on bright colours and prominent brand logos, and you’ve got a fashion disaster on your hands. 

A bucket hat provides a little protection from the sun and has a reputation for ‘fun’, so it’s survived as an ironic wardrobe fave at summer festivals. But if you’re wondering what to wear on a first date, ‘ironic’ shouldn’t be in your vocab. Unless you’re planning on spending your first date at Glastonbury, you should keep the bucket hat at arm's length.

Trucker Hats

trucker hats

Next up in our must-avoid men’s hats is the trucker hat. A trucker hat is a version of that men’s fashion staple, the baseball cap. They’ve got the same long, curved bill that a baseball cap has, but trucker hats have mesh backs instead of cotton. 

Trucker hats have been around for decades, but they didn’t become fashionable until the early 2000s. Big names of the noughties like Justin Timberlake and Ashton Kutcher were often seen sporting a trucker hat. They’re meant to associate the wearer with the laid-back, down to earth truckers featured in that classic seventies hit ‘Convoy’. 

But like the bucket hat, the trucker hat’s time as a stylish piece of headwear is long gone - after all, we’re twenty years into the 2000s! Not to mention, this was the era of low-rise jeans, double denim, giant belts and skinny scarves, so can we really trust the fashion trends from back then?

The Beanie


We’ve saved the last entry in our list for the most controversial pick: the men’s beanie hat. We know, we know! Fedoras and bucket hats are one thing, but beanies are quite another. They’ve been a popular men’s fashion accessory for decades, so what gives?

Listen, the men’s beanie hat is perfectly acceptable if it's chilly. Keeping warm is important, and if your beanie is fulfilling a practical purpose then there’s nothing wrong with wearing one. They can even look quite complementary when paired well with a stylish outfit.

The problem with the men’s beanie hat is that it’s often not worn correctly. Many guys wear them loosely, with their ears poking out. This leaves the hat sticking up off your head, giving you more of a Papa Smurf vibe than a nineties skater boy. Instead, make sure you roll the edges of the beanie up so it stays fitted tightly against your skull. 

The other reason you should avoid a men’s beanie hat is that they’re one of the biggest causes of chronic hat hair. Pull off this tight fitting hat and all too often you’ll see your once perfectly coiffed hair sticking out at all angles - not the best look for a first date! Wearing a beanie in the summer is also a big no-no, unless you want a sweaty, sticky brow.

Ready to hit the dating scene?


Deep breath fellas, we’ve come to the end of our list of fashion faux pas to avoid on a first date! There’s just one question remaining: What kind of mens hats should you wear instead? A baseball cap is a good choice, although with so many caps out there it’s going to be tough to sort the wearable from the burnable. Luckily, we’ve written a buyer’s guide just for you: the most fashionable men’s baseball caps for 2021. And, if there’s a cold snap just before your date begins, check out our picks for the best and warmest winter hats for men.

Just like any outfit addition, it’s not what you wear - it’s how you wear it that counts. If novelty hats and fedoras are your style, then wear them and, more importantly, wear them with pride! And, hey, if you can pull off a second date in one of these hats, you’re definitely a secret smooth operator! Nice.