8 Hats to Wear with Suits and Other Menswear Looks

8 Hats to Wear with Suits and Other Menswear Looks

Lest you thought “suit” and “hat” would never belong in the same sentence much less the same outfit du jour — let me clear that up right now. 

It does. 

And it looks damn hot! 

So let’s talk about hats to wear with suits. Because a perfectly-placed men’s fedora or well-worn men’s wide brim hat turns the every-man’s suit or slacks-and-top combo into a show-stealing smoke show of an outfit.

It shows style. 

It shows attention to detail. 

And it shows off that sexy scruff or a chiseled jawline. None of which will garner any complaints from those around you.

But wait, is it weird to wear a hat with a suit or dress clothes?

Is it weird to show up to work, a wedding, or a formal evening event as the best-dressed man in town?

No, it’s not weird. There are plenty of hats that go with suits and other menswear looks. In fact, wearing a hat with dress clothes has been the status quo for years. 

Think about the tweed flat cap, or newsboy hat, worn by Cillian Murphy’s character in Peaky Blinders. He finished the look with a full wool suit and gangster’s swagger.

Or consider the many men’s hat styles donned by the dapper men of Downtown Abbey. Over six seasons, we saw white woven men’s sun hats, wide brim men’s fedora hats, classic black top hats, and casual brown wide brim felt hats worn by England’s elite in the early 1900s.

For the early 20th-century man, a suit and hat was a daily staple.

For the 21st-century man, it’s about making a statement. And understanding the types of hats that go with suits.

And that’s why you’re reading this.

Compilation: 8 Modern Ways to Wear Men’s Dress Hats

Big hat energy is the new BDE (or, Big Dick Energy, which is so 2018). And yes, it works just as well on the red carpet as it does in the real world — like a work meeting, happy hour, wedding, brunch date, or a dressed up night out. 

Mystery, style, and a unique flare all rolled into one, these stylish men with their red carpet looks are serving all the inspiration you need to throw on a men’s suit hat before leaving the house this weekend. 

Whether or not you actually pair it with a suit is up to you.

1. Add a Casual Touch to a Buttoned-Up Look

Octavio E Rodriguez wore a flat brim, tan fedora with a plaid three-piece suit in London.
Octavio E Rodriguez wore a flat brim, tan fedora with a plaid three-piece suit at the 65th BFI London Film Festival (Karwai Tang/WireImage).

Let’s start this out with a timeless winner: the three-piece suit and hat ensemble. Seen here on Octavio E. Rodriguez while attending the Ron’s Gone Wrong World Premiere during the 65th BFI London Film Festival. His clean-cut look featured an all-over plaid print in navy and light blue with a navy tie and tan wool felt hat

The high crown, pronounced pinch, and brown leather hat band on his fedora add just a bit of casual western style influence to his otherwise modern-working-man look. It gives us the vibe that he just threw on his hat while running out the door.

When you think about hats to wear with suits, a tan fedora paired with navy and steel blue are not the usual suspects. And that’s what makes this outfit work. The light color palette and plaid print will always stand out in a sea of black tuxes. The suit is formal, but pairing it with a casual wide brim fedora makes Rodriguez seem approachable, laid back, and warm. 

2. Anchor a Bold Blazer With a Timeless Classic

Major R. Johnson Finley wore a black boater hat and gold blazer in NYC
Major R. Johnson Finley wore a black boater hat and gold blazer during the 15th Annual ADCOLOR Awards in New York City (Jared Siskin/Getty Images for ADCOLOR).

Sometimes a classic-yet-never-boring black boater hat is just the thing you need to anchor an otherwise busy outfit option. But let’s not mistake busy for bad here, because it’s anything but.

The summery white denim worn in the fall, the luxe silk blazer paired with a casual screen print tee shirt – the juxtaposition of these items make them feel both at odds with each other and extremely complementary. Like the yin to a yang, Major R. Johnson Finley expertly pulled together multiple pieces that shouldn’t — but do — work together. 

He topped it all off with a black pork pie hat that adds more style with a stand-out silhouette. But it also adds refinement to the look with a sleek, all-over color and no hat band.

This would work just as well off the red carpet, but take note of a few things to ace the effortless style Finley has here. First, consider the black hat. It’s clean, has sharp lines, and matches the black tee and armband, bringing together multiple items into one color story. Then we have the white lettering on his tee shirt matching his white jeans. And finally, that gold statement blazer mirrors the sheen of his round-toe boots. And so you see, a suit and hat outfit that looks like an accidental win has a lot of very intentional elements. 

3. Keep It Clean with a Black Trilby And Matching Shoes

A guest wore a black men’s trilby hat with matching black sweater, watch, and boots in NYC
A guest wore a black men’s trilby hat with matching black sweater, watch, and boots at a Hulu premiere in New York City (Roy Rochlin/WireImage).

Wise dressers know that matching your belt and your shoes is a way to look instantly put together. 

This man applied that same logic when thinking about hats to wear with suits. Or in this case, the hat he wore with his matching top, watch, and lace-up black leather dress shoes while attending Hulu’s Dopesick New York premiere at The Museum of Modern Art. 

The mystery attendee looked comfortable yet completely polished in a black woven trilby hat (worn slightly to the side), fitted skinny jeans, and a long-sleeve black shirt. Most men probably have these items sitting in their closet already. And, when worn together they create an understated, yet undeniably sexy look.

A classic, curved brim men’s trilby has long been considered one of the more traditional hats that go with suits. And that’s exactly why I might suggest you take a cue from our style inspiration here and wear it with anything but for your next night out.

4. Nix The Neutrals For a Look That Gives Big Energy

Jon Gist wore a tan and red wide brim fedora in LA
Jon Gist wore a tan and red wide brim fedora to the Twenties Season Two screening and Black Canvas Viewing Experience in LA (Leon Bennett/Getty Images for BET).

Real BDE speaks for itself. And the choice hat of Jon Gist, VP of Brand Strategy and 360 Marketing at BET did a whole lot of talking.

The tan men’s fedora with a subtle pinch in the crown featured a contrasting bright red color on the underside of the brim. Brim edge trim is hot these days and the red carpet hue of his hat implied he was right at home in the spotlight – and helped him stand out at the Twenties Season Two screening in Los Angeles. 

The wool fedora with a red bottom brim also looked great with those silk plaid Burberry pants, which he dressed down with a pair of fresh white and silver sneakers.

Was this look inspired by the bold red under brim hat style worn by Chef Marcus Samuelsson at the 2021 Met Gala? It’s a mystery. 

But what we do know was that this wasn’t the first time Gist and this fantastic fedora turned heads and stopped scrolls. He was seen snapping IG pictures while brunching at Breakfast at Barney’s earlier in the year. He wore the same hat and much more casual fit. 

The fedora in question once again elevated his look — this time some cuffed ripped jeans, crisp white shirt, and Gucci loafers. This showed us that a dress hats don’t need to be confined to the limits of evening wear — and that all you need to try on a bold new look is a classic white button up and some well-tailored pants.

5. Channel Your Inner Rock star with Patterned Bands and Jewel Tones

Leiva wore a taupe wide brim felt hat with a cloth hat band and emerald suit in Ibiza
Leiva wore a taupe wide brim felt hat with a cloth hat band and emerald suit at the 40 Principales Music Awards Nominees Gala Dinner in Ibiza (Isabel Infantes/WireImage).

If you live outside of Spain, Leiva may not be a rock star you know. But when it comes to learning which hats to wear with suits, one glance at this flashy look is enough to confirm that he’s the style icon you know you need. 

Let’s unpack his suit and hat look.

An emerald green, slim cut silk suit with gold buttons and a red silk lining that peeks out from the sleeves looks glamorous. Perfect for a music awards dinner in Ibiza. Meanwhile, merlot leather shoes, a wide brim fedora with a creased, pinched crown and tattered cloth hat band, and a patterned shirt with just a few extra buttons undone to show a bit of Leiva’s chest tattoo add the strong dash of rock star edge you’d expect from one of the night’s nominees.

To make a hat go with a suit like this, it can’t be too refined nor rough around the edges. Leiva’s taupe felt topper hit the sweet spot with a high crown and super-pronounced pinch. Of course the piece that really pulls it into the rest of his look is the double-layer cloth hat band, which mimics the pattern of his shirt and adds a bit of rugged rock star vibes with a frayed edge.

Keeping his prints in the same black and white color scheme and adding subtle edgy touches ensures his suit and hat combo stays buttoned up and appropriate for a formal affair, while coming undone just a bit. Flip the brim down for a gangster hat look.

6. Bring Out Your Best Street Style with a Black Bowler Hat

Diong-Keba Tacu wore a black bowler hat and corduroy jacket in London
Diong-Keba Tacu wore a black bowler hat and corduroy jacket at the 65th BFI London Film Festival (Ian Gavan/Getty Images for BFI).

You may not need your most formal men’s dress hat for an evening out. You might take one look at the most common men’s hats to wear with suits and decide the black bowler hat style is destined for other things. Originally designed as a more versatile hat option than the traditional top hats of the time, it only seems right that we continue to push the sartorial limits of the round, tight-crowned bowler silhouette. 

Enter Diong-Keba Tacu with his military green pleated pants, black tee shirt, and sepia corduroy jacket at the 65th BFI London Film Festival. 

This look is put together by muted tones and driven by comfort — which is what you want for movie night. He could have stopped there, but he topped it off with formal leather shoes and a black bowler hat with a rust-colored feather plume sticking out of the silk hat band. These two pieces put the final polish on this outfit, taking it up from ordinary to absolutely delightful, without trying too hard. 

And, should future occasions call for a collar and two-piece, that black bowler hat definitely makes the cut for hats to wear with suits.

7. Flip The Script With Dramatic Silhouettes

Jante Harris word a beige men’s wide brim hat, sleeveless suit, and square handbag in NYC
Jante Harris word a beige men’s wide brim hat, sleeveless suit, and square handbag to the 15th Annual ADCOLOR Awards in New York City (Jared Siskin/Getty Images for ADCOLOR).

A man in a style league of his own, Jante Harris wore a gender-fluid fit that came together with gold accessories. Like a cherry on top of a sundae, this sartorial feast was topped with a beautiful beige hat that had a slight dusting of a rust accent color on the brim and at the pinch points.

There’s a lot to love here, but I appreciate the structured lines most. It starts at the top with a strong horizontal line in his hat’s wide brim and then moves down to horizontal lines, where his chest and arms are highlighted with a low v-neck cut and sleeveless suit top. Finally, the clean, geometric lines culminate in the structured gold piping on his handbag. 

A simple suit to bring you into 2022? I think not. Harris shows us that a bold wide brim hat slightly turned up is definitely one of those hats that goes with suits — especially if that suit is anything but expected. 

I could see this in a creative work setting. The modern power suit worthy of the power moves you’ll be making as you climb the corporate ladder. So what if you’re closing deals and asking for a raise via Zoom? A big hat brings big energy — and a wider brim, the better for meeting your stretch goals. Plus it shows all those teleconferencers you didn’t come to play screen games. You take yourself and your career seriously. Serious enough to take fashion risks even when they can see your bed in background.

8. Keep Your Cool with a Floral Flare Hat Band

Serge Ibaka wore a white wide brim hat with a floral hat band and grey pinstripe suit in LA
Serge Ibaka wore a white wide brim hat with a floral hat band and grey pinstripe suit at the premiere of The Harder They Fall in Los Angeles (Rich Fury/Getty Images).

Speaking of unexpected fits that just might work at work. Is that a hibiscus flower and neon trim I spy on the hat band of Serge Ibaka’s white felt hat? And did he pair such a casual men’s sun hat with a gray, double-breasted pin stripe suit?

He did indeed.

Sure you have to work. But that doesn’t mean your heart and head (and hat) can’t be already clocked out with your toes in the sand. 

Ibaka’s outfit is the best of both worlds. He balances a 9-to-5 fit with a vacation vibe by giving a formal suit and hat look a relaxed fit. He went for a wide necked tee instead of a collared shirt, a slightly relaxed fit instead of a tightly-tailored one, and left his sport coat unbuttoned.

It’s giving work, but make it Cali vibes. 

Indeed, this is the perfect suit and hat combo for more laid back office environments or casual evening events.

The Hat Stops Here

The delicious menswear trend that is big hat energy is gracing red carpets around the world. And I love to see something stirring up the classic suit ensemble or slacks-and-top combo for the better-dressed men among us. 

Pair a classic, well-tailored suit with a western-inspired, wide brim fedora hat for a little more relaxed outfit. Use a bright red under brim or floral print hat band to bring a pop of color and playfulness when you suit up and show. Or give your formal attire a night off and dress up your look with a men’s felt fedora or black bowler hat instead. 

What I’m saying is this, “Guys, girls, gays, and theys, you’ve got options!” 

You don’t need permission to steal these looks for yourself. If you’ve been researching which men’s hats to wear with suits, here’s your sign. You don’t need an excuse to peruse the selection of men’s dress hats out there and up the ante on your suit with an unexpected mix of cuts, colors, and hat silhouettes.

No matter who you are or what your style, it’s time to think outside of the box when it comes to formal menswear. And we’re here to offer you guidance when it comes to knowing the best hats to wear with suits and other men’s looks.

Leave a Comment

Your email address will not be published. Required fields are marked *

19 − five =