16 Hats that Will Keep You Warm & Complete the ’Fit This Outdoor Dining Season

I’m with your mom here: if it’s below 45 degrees and you’re sitting outside for 90 minutes, you need a hat. But that does NOT mean you have to sacrifice the fit.

As someone who isn’t quite comfy with indoor dining, but is obsessed with the Boston food scene, I find myself braving the freezing winter temps on the regular to get my dining fix. And no matter how much I want spring to arrive, I'm still stuck with chilly winter temps for now. Because of that, I also find myself standing in front of my closet for absurdly long periods of time, attempting to plan outfits that are stylish and warm. There is a caveat, though: when dining outside, I find I actually cannot take off my coat. It’s too damn cold. (I don’t care what they say; outdoor heaters just don’t cut it).

But there is a way to salvage the ’fit, I promise. It’s all about the accessories! An assortment of chic coats — from big puffers to boxy breasted jackets — is a must. Another must? Scarves and gloves. Let’s face it, though, it’s easy to find cute scarves and gloves, and even easier to wear them. That leaves us with... hats. I used to believe they were a necessary evil that I could shirk off the moment I turned 18 and didn’t have my mom insisting I maintain a warm head. But I have to be honest here: my head does get cold. After trekking outdoors to college classes on freezing winter days, I came to realize the necessity of the hat. It may have taken me a bit to embrace that I couldn’t get by without one, but once I began my foray into the cute-hat world, I was hooked. Hats are great. 

Now, just because you are technically dining at a restaurant, it does *not* mean you can’t wear a hat. Since you’re outdoors, it’s perfectly acceptable to sport one, and if it’s stylish, your outfit will be better for it. So here’s my best compilation of 16 affordable hats that will keep you warm and complete the ’fit. Time to (safely) indulge in the outdoor restaurant scene at your leisure!

  1. 1. ASOS Design Fluffy Bucket Hat in Cream

    ASOS Fluffy Bucket Hat in Cream

    Minimalist aesthetic + 2021 winter accessory trend = the crossover episode we didn’t know we needed. Not only will this hat keep you warm, but it will have your friends mistaking you for an Instagram style blogger, guaranteed.

    ASOS Design, ASOS, $20, shop now

  2. 2. Sky Blue UO Plush Sherpa Bucket Hat

    UO Blue sherpa hat

    This is a variation on the fuzzy bucket hat trend, so it’s perfect for winter, yet this hat sports a pastel color reminiscent of spring. The best of both seasons!

    Urban Outfitters, $29, shop now

  3. 3. UO Check Fleece Bucket Hat

    UO check fleece bucket hat

    This hat features a stand-out pattern and a splash of color that’ll make any ’fit pop — plus, you’ll be easily recognizable in crowds (although for COVID reasons, probably best to stay away from those).

    Urban Outfitters, $29, shop now

  4. 4. Princess Polly Leopard-Print Faux Fur Bucket Hat

    Faux fur leopard bucket hat

    As far as winter bucket hat materials go, we’ve seen plush, fleece and now I must introduce faux-fur, a material so soft that you’ll have to stop yourself (and others) from petting your head. This hat comes in a classic animal print, with a color palette that will match every coat you own, so you can throw it on as you walk out the door and feel confident that it’ll just ~go~. 

    Princess Polly, $26, shop now

  5. 5. Zara Quilted Bucket Hat

    Zara quilted bucket hat

    Now this will *definitely* keep you warm. It’s like a down jacket for your head, and therefore perfect for outdoor dining because you won’t think twice about getting cold. The only potential downside is the static that will probably mess up your hair, but at least it’ll be even more incentive to keep the hat on!

    Zara, $25.90, show now

  6. 6. Krystal Dyed Bucket Hat

    Krystal dyed bucket hat

    This hat might not keep you as warm as the previous one, but it’s a hat, isn’t it? Plus, tie dye is having a moment (though it’s been a while — maybe time for it to take a backseat?)

    Urban Outfitters, $15, shop now

  7. 7. Indigo UO Frayed Bucket Hat

    UO frayed bucket hat

    The distressed texture of this hat will have your friends ogling. Not only is it easy to pair with any outfit, but it’s a ’fit all on its own.

    Urban Outfitters, $24, shop now

  8. 8. Ribbed Beanie in Sea Green

    ribbed beanie zara

    I couldn’t make a compilation of winter hats without including the illustrious beanie! And this one from Zara pays homage to the style’s skater-boy roots, without sacrificing color, warmth or style. (It’s also 75 percent off at $3.99!)

    Zara, $3.99, shop now

  9. 9. Merino Ribbed Beanie in Painted Leopard

    leopard print beanie

    If you’re looking for a beanie with a bit more of a “look,” look no further than this animal print-esque beanie from Madewell, the long-reigning queen of tasteful animal prints. Just check out their sneaker and scarf collections; you’ll see what I mean. This beanie features a hint of girly vibes, too, making it perfect to dress up any outfit, simple or complex!

    Madewell, $29.99, shop now

  10. 10. White Knitted Beanie with Faux Fur Pom Pom

    Amazon knit beanie with faux fur pom pom

    ...And we’ve entered pom-pom territory. Winter just wouldn’t be winter without a pom-pom on every street corner. This affordable version from Amazon Fashion will be cozy and clean. Who’s to say pom-poms are only for the slopes? I say let’s show 'em off! From outdoor gatherings to outdoor dining, to even walks and hikes, “versatile” is this hat’s middle name.

    Furtalk, Amazon, $16.99, shop now

  11. 11. J. Crew Purple Ribbed Beanie with Faux Fur Pom Pom

    Purple jcrew beanie with pom pom

    This beanie, currently 71 percent off on J. Crew’s website + 50 percent off with code GOSPRING (so grab it while you can), has the ultimate winter chic vibes. Think hot cocoa and s’mores kinda vibes. It just doesn’t get better than that.

    J. Crew, $12.99, shop now

  12. 12. Columbia Winter Blur Pom Pom Beanie in White

    columbia winter blur pom pom

    Though this hat is a bit more pricey than the others, it’s an investment that will be worth your while, as it can transition from the sidewalks to mountain peaks, and everywhere in between. And from a beloved outdoor retailer like Columbia, you can be sure it’s built to last. (Plus ASOS has a great student discount program!)

    Columbia, ASOS, $35, shop now

  13. 13. Zara Taupe Soft Feel Cap 

    Soft Feel cap zara taupe

    I’m not one to believe that baseball caps can keep you warm, but what if it’s made of such a soft fabric? Interest = piqued. So when you combine a baseball cap with a gorgeous (not to mention on-trend) color, and extra-softness, I think it’s a safe bet that it’ll keep you warm and complete the ’fit.

    Zara, $25.90, shop now

  14. 14. Aerie Fleece Headband in Heather Grey

    Aerie Fleece headband

    Not feeling the hat life? That’s okay; some people just don’t love hats. Seriously, no shade. But just because you’re not crazy about hats doesn’t mean that your head should have to be freezing or that you’d have to wear a … *gasp*... hood. Try something like this instead, a fleecey headband featuring an adorable top not, that effortlessly avoids the hathair conundrum.

    Aerie, American Eagle, $12.95, shop now

  15. 15. ASOS Design Chunky Knit Headband in White

    ASOS chunky knit headband

    Here’s another headband for our hat-haters out there, though this one is knit, channeling the classic cable-knit sweater vibe. Plus, it’ll be so cozy, you probably won’t ever want to take it off!

    ASOS Design, ASOS, $11.50, shop now

  16. 16. Zara Wool Beret in Mid-Green

    Wool beret Zara

    Looking to make a statement? This beret has you covered. It’s affordable and precious, and Emily in Paris would be proud. Plus, the hat comes in Spring-y green and a bright mustard, separating this version from just any old French traditional hat, bringing in a minimalist, post-modern edge. Is there anything more 2021 than that? 

    Zara, $25.90, shop now

These 16 hats are without a doubt the 'go-to's you’ll be sporting this winter. From fuzzy bucket hats to leopard print beanies, friends, family and strangers will be admiring your style. You’re welcome.

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