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 caps for men, or newsboy cap, 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 flair 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

Let’s start this out with a classic winner: the casual button-down and hat ensemble. As seen in this image, this clean-cut look features a deep navy shirt layered comfortably over a dark crewneck tee, perfectly topped off with a dark brown wool felt fedora.

The structured crown, subtle pinch, and matching band on his dark brown felt fedora add just a bit of classic, rugged charm to his otherwise modern-working-man look. It gives off an effortless vibe—like a sharp finishing touch he casually grabbed while heading out the door.

When you think about adding a hat to everyday casualwear, a dark brown fedora paired with a deep navy button-down isn't always the usual suspect. And that’s exactly why this outfit works. The rich tone-on-tone color palette understatedly stands out without trying too hard. While a structured felt hat can sometimes skew formal, pairing it with a relaxed, open-collar shirt makes the look feel entirely approachable, laid-back, and warm.

2. Anchor a Bold Blazer With a Timeless Classic

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 makes them feel both at odds with each other and extremely complementary.

Men's pork pie hat 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 key details to ace this effortless look.

First, consider the black hat. It’s clean, has sharp lines, and matches the black tee and armband, bringing together multiple items into one cohesive color story. Then, the white lettering on the T-shirt seamlessly pairs with the white jeans. Finally, that gold statement blazer mirrors the sheen of the round-toe boots.

What might look like an accidental win actually relies on a lot of very intentional elements.

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

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. 

This ensemble looked completely polished in a black woven trilby hat, navy button down. and black shoes. Most men probably have these items sitting in their closets already. And, when worn together, they create an understated, yet undeniably sexy look.

A classic, curved brim mens trilby hat 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. Mix The Neutrals For a Look That Gives Big Energy

The tan men’s fedora with a subtle pinch in the crown features a dark brown bound edge along the brim paired with a matching multi-toned ribbon band. Brim edge trim is a stylish detail these days, and the rich brown accents against the natural woven straw make this piece effortlessly stand out—adding a refined finish to a breezy, casual look.

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

A classic fedora effortlessly elevates any everyday ensemble—even one built around cuffed ripped jeans, a crisp white shirt, and sleek loafers. It’s proof that a structured hat doesn't need to be confined to formal evening wear, and that all it takes to pull off a bold new style is a timeless white button-up paired with well-tailored pants.

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

When it comes to learning which hats to wear with suits, one glance at this flashy ensemble is enough to provide the ultimate style inspiration. Let’s unpack this standout suit and hat look.

An emerald green, slim-cut silk suit with gold buttons and a red silk lining peeking out from the sleeves looks effortlessly glamorous—perfect for a high-profile evening event.

Meanwhile, merlot leather shoes, a wide-brim fedora with a creased, pinched crown, and a patterned shirt left undone just enough to reveal a bit of chest tattoo add a strong dash of rock-star edge.

To pair a hat with a suit like this, it can’t be too refined nor too rough around the edges. This taupe felt topper hits the sweet spot with a high crown and a super-pronounced pinch.

The piece that really ties the look together is the double-layer cloth hat band, which mimics the pattern of the shirt and adds a touch of rugged charm with its frayed edge.

Keeping prints in a cohesive black-and-white color scheme while adding subtle edgy touches ensures the suit and hat combo stays appropriate for a formal affair, while feeling stylishly relaxed. Flipping the brim down brings a classic, vintage-inspired silhouette to the entire look.

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

You may not need your most formal dress hats for men 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. 

Consider an ensemble featuring military green pleated pants, a black t-shirt, and a sepia corduroy jacket.

Brought together by muted tones, this look is driven by comfort—perfect for a relaxed evening out. The outfit could easily stop there, but it is elevated with formal leather shoes and a black bowler hat featuring a rust-colored feather plume tucked into its silk band.

These finishing accents add the final polish, taking the outfit from ordinary to absolutely delightful without trying too hard.

And should future occasions call for a collar and a two-piece suit, that black bowler hat easily transitions into a top choice for pairing with formalwear.

7. Flip The Script With Dramatic Silhouettes

In a style league of its own, this outfit 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 the hat’s wide brim and then moves down to horizontal lines, where the 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 the handbag.

A simple suit to bring you into 2022? I think not. This look 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 is 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 the background.

8. Keep Your Cool with a Floral Flare Hat Band

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 this white felt hat? And is such a casual men’s sun hat paired with a gray, double-breasted pin stripe suit?

It is 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.

This outfit is the best of both worlds. It balances a 9-to-5 fit with a vacation vibe by giving a formal suit and hat look a relaxed fit. It features a wide necked tee instead of a collared shirt, a slightly relaxed fit instead of a tightly-tailored one, and leaves the sports 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.