I had to wear a straw hat every day at school for eight very long years — it was a private school in Australia with British heritage, so they knew how to dress stupidly — and this made me somewhat reluctant to get one as an adult. Still, there’s something very practical and attractive about a brimmed hat that’s lightweight and keeps the sun off your brow while letting air and wind through.
I think most guys want to have a brimmed hat but worry they’ll look like a dork. I get it, hats are hard to pull off, but we’re not talking about wool fedoras here. No one’s doing Indiana Jones cosplay.
But boy, can it be intimidating to buy a hat. Fedoras and trilbies and bowler hats are too formal, baseball caps and beanies are too informal. That’s why we’re recommending the straw hat for all your summer needs. The best men’s straw hat finds a nice balance between formal and informal that makes it look good with a summery suit or with swim shorts.
So how the heck do you determine what makes a nice straw hat? They might seem like they’re just straw and maybe a ribbon or some leather, but materials play a big part, the type of straw, where it’s sourced from, and then there’s the craft: the fineness of the weave, how even the weave is, and even the direction of the fibers play a big part.
We’ve listed the best straw hats on the market and to make things easier we’ve divided it up into entry level — our fancy way of saying “under a hundred bucks” — and then mid-level and then high end, which are over $200.
- REI – Sunday Afternoons Havana Hat ($34)
- Brixton – Wesley Straw Hat ($49)
- Stetson – Stratoliner Milan Fedora ($93)
- Two Roads Hat Company – Wynwood ($105)
- Yellow 108 – Stevie ($118)
- Will and Bear – Rider ($129)
- Goorin Bros – Big John ($160)
- Borsalino – Argentina Raffia Crochet ($290)
- Super Duper Hats – Yuma (€310.00) (~380USD)
- Optimo – The Optimo ($600-$5,000)
1. REI – Sunday Afternoons Havana Hat ($34)
- Great price for entry level hat dudes
- UPF 50 rating
- Only has two sizes
- Not great in the rain
The cheapest on our list is still a pretty darn nice hat. It’s the Sunday Afternoons Havana hat from REI has 50 UPF rating, meaning it’s got the highest sun protection you can get. The brim is 2.75 inches for some solid shade, it’s got a sweatband, and it has a nice, versatile look.
It’s worth noting that it’s not technically straw, it’s 90 percent paper and 10 percent polyester. Now there are a lot of high quality paper hats out there (shantung straw is a high performance paper that’s very durable), but this particular hat doesn’t do well in the rain. In fact, you’re not meant to let it get wet ever, but hey, it’s only thirty-four bucks.
2. Brixton – Wesley Straw Hat ($49)
- Comes in 5 sizes
- Two colors
- Leather head band
- Floppy brim makes it less fashionable and structured
The Wesley Straw from Brixton comes in an impressive array of sizes: five of them, compared to the Havana Hat’s two sizes, plus you can pick from two different colors. The hat has a leather band and interestingly, you’ve got an adjustable velcro strap under the sweatband to get a more secure fit. It’s $49 and yes, it’s made with one hundred precent straw. The main potential downside is that the brim isn’t very structured; it’s floppy, neither stiff nor cowboy-ish, which makes it a little hard to wear away from the beach.
3. Stetson – Stratoliner Milan Fedora ($93)
- Handmade in Texas
- Comes in 7 sizes and four colors
- Cool touches like satin liner, cowhide sweatband, and airplane shaped pin
- Regularly sold out; Stetson has trouble keeping up with demand
The Stetson Stratoliner has to get a mention — it’s one of the most iconic hats from one of America’s most iconic hat companies, and they were even licensed to make Indiana Jones branded hats around the release of Temple of Doom.
Stetson is a very solid brand that makes all their hats by hand in Texas. This one has seven sizes and four colors to choose from, it’s firmer than the other hats we’ve mentioned so far and there are a lot of cool touches like a satin liner, a cowhide sweatband, and a cool hat pin that’s shaped like a stratoliner airplane.
Two Roads Hat Company – Wynwood ($105)
- High-quality handmade straw hat
- Sharp looking hat with satin lining and leather sweatband
- Stiff, flat brim
- Rigid, so it’s harder to transport and some may find less comfortable
Now onto our mid range hats. First, we’ve got Two Roads’ Wynwood, the company’s flagship straw hat that comes in at $105. This is a really sharp looking hat that’s simple but it’s high quality, with a nice leather sweatband and satin lining. Noticeably higher quality than the previous entries in this list, it’s made with stiffened straw and a flat brim that makes for a good combination of stylish and casual.
If you buy hats like this because they’re great symbols of Americana you may be put off by the fact that it’s made in China, but that’s why the price-to-quality ratio is very solid and we have no qualms saying this is one straw hat that looks as good at the beach as it does in Manhattan. (I’ve worn it in both.)
5. Yellow 108 – Stevie ($118)
- Yellow 108 is a sustainable company
- Made in the USA
- Limited sizes and colors
- Often sold out
Yellow 108 is a less well-known hat maker, but they still make really cool stuff. With a good pricepoint for American made hats, the brand focuses a lot on sustainability: they use no glue, no plastic bags, their hang tags are made with recycled paper, and their salvaged leather trims are made in a solar- and wind-powered facility.
Made with real straw in the United States, the Stevie has a nice classic crown shape with a folded and sewn brim edge that will keep its stiff and flat shape. The hat comes in four sizes and is made with 100 percent palm straw, and it can work with summer suits and board shorts alike.
6. Will and Bear – Rider ($129)
- Lightweight, breathable material
- Cool features like a leather lanyard
- Unusually eco-friendly approach; brand plants ten trees for every hat purchased
- Wide brimmed, but a bit flimsy and floppy
The Will and Bear Rider hat is unlined with a floppier brim than the Stevie. Coupled with the leather lanyard and large, 3.5-inch brim, and you’ve got a decidedly beachy hat that doesn’t dress up well, but it’s perfect for the beach, hikes, and anything casual and outdoors.
Will and Bear is a brand with a strong Australian bent to it. It’s unclear if the founders actually are Australian (so they probably aren’t) but they take their design cues from classic Australian headwear, and their wool hats are made with Australian merino. The Rider comes in three sizes and two colors and it’s made with 100 percent palm fronds, which are really lightweight and breathable.
Will and Bear has a really legit eco-friendly angle: they only use organic cotton (so no pesticides), they donate a percentage of their profits with biodiversity and rainforest rescue organizations, and they plant ten trees for every hat sold.
This is a comfortable hat, but remember that it’s a bit flimsy and best suited for informal situations.
7. Goorin Bros – Big John ($160)
- Made in the USA
- They use real toquilla straw
- 5 Sizes and two colors
- Tightly woven straw, so it’s not the most breathable hat on the market.
No list of great hats is complete without a mention of Goorin Bros, a great brand that’s often the first thing New Yorkers think of when they hear the word ‘hat.’ The hats are made in the US from real toquilla straw, a natural fiber from Ecuadorian palm trees that for centuries has been used to make the famous Panama hat.
The Big John is $160 and comes in 5 sizes and two colors, and what’s nice is that unlike some toquilla straw hats it doesn’t have an especially loose weave so it’s great at actually protecting from the sun — it’s even received a coveted UPF 50 rating and 98 percent UV radiation block.
8. Borsalino – Argentina Raffia Crochet ($290)
- Esteemed, 150+ year old company
- Made with raffia, considered the most durable straw
- Surprisingly flexible
- Soft brim might make it less formal than some would expect
The first high end hat we wanted to mention the Borsalino’s crochet raffia, which I picked up for this review. It’s not cheap, but there are a lot of interesting things here. For starters, it’s a Borsalino, a company that was founded in 1857 and has a ton of history — they’re best known for making the most iconic hats worn by gangsters in the 1920s and 30s. Al Capone famously refused to take his Borsalino off for his mug shot.
This hat is called the Argentina, has a 2.75-inch brim, and it’s inspired by wide-brimmed roll up Argentina hats and the English Arts & Crafts movement of the late 19th century. That isn’t about finger painting; it was a philosophy advocating the rejection of modernity in favor of a romantic revival of medieval and folk aesthetics. So I’d say they’d be at home in the heritage men’s fashion scene.
It’s made of raffia straw, which is considered the most resilient straw material. It’s from a palm tree native to tropical regions of Africa and it’s heavier, more durable, and better at sun protection than other kinds of straw while also being surprisingly flexible — you can actually roll the hat up for travel —so combine that with the fact it’s handmade in Italy and you start to see how the higher price tag is justified.
9. Super Duper Hats – Yuma (€310.00) (~380USD)
- Versatile look, not too formal, not too casual
- Nice details like the gros-gain ribbon
- Made of Ecuadorian Quito straw
- Silly brand name for such a cool hat
- Has to be shipped to the US
- Very expensive
Ok, here’s the Yuma from Super Duper Hats. Honestly if someone said “nice hat, what’s the brand,” I would not want to admit to wearing a super-duper hat. But, silly name aside, this is a really cool hat. It comes in six sizes, which includes five numbered and a one-size fits all.
I’d name this the best looking hat that has a really wide brim, clocking in at 3.5 to 4 inches depending on the dimension of the raw hat body. With a straight, stiff brim that gives it a really clean look, it has a strongly pinched crown that, combined with the flatter brim, make for a hat that’s more international and less like a traditional cowboy hat than many other offerings.
The material is an Ecuadorian “Quito” straw and they put a lot of thought into the trim as well, coming with a classic gros-grain ribbon with a heavier weft than warp, giving the ribbon a nice texture. The bows of the ribbon have raw-cut edges, making a bit less formal looking. Want something a little brighter? Check out the Yuma II and it’s slightly more subtle 3.1-inch brim.
10. Optimo – The Optimo ($600-$5,000)
- All are handmade and custom fitted in their Chicago store.
- Highly customizable, rim size, ribbon, shape of the dome, lining, color, weave style.
- Boy howdy, is it expensive.
- You have to go to Chicago to buy one, which isn’t that bad. Chicago is cool city.
Now for Optimo’s Montocristi Panama hat. When you’re talking about the “best” of something, well, this is it. This is their signature model, but they have several straw models including the Porkpie, Gambler, and Classic Fedora.
They’re all completely hand made and custom fitted. Indeed, the only way to get this hat is to be measured in their Chicago store, where it’s then made to order with old world techniques in Ecuador. You chose the exact rim size, ribbon, shape of the dome, interior lining, color, and weave style.
The quality of a hat at this pricepoint is determined in large part by the weave, the uniformity of the weave, and the straw itself. When you hold it in your hand, you can see how finely the weave is achieved, and Optimo even guarantees a lifetime of free maintenance: you can send the hat in and have it repaired and restitched at any time.
Optimo has outfitted thousands of musicians and actors, and since you can customize the ribbon, the color, the style, the brim, and more, you can be sure you’ll be able to craft the perfect hat for your style.
Wrapping it Up
From the absolutely basic entry level hat from REI to the super luxury, custom, made-to-measure Optimo hat, we think we’ve landed on the perfect list of the best straw hats for men. Let us know in the comments which one you’d want to pick up! Personally, I’ve landed on the Two Roads and the Borsalino, but I may be clicking ‘purchase’ on the Will and Bear some time soon.
Thanks to Jon Shanahan at The Kavalier for his help putting together this article. Check out his site and YouTube channel.
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