March 07, 2022


Whether it’s winter, fall, spring, or summer, a coffee date is always in season. Now that you're here, we're going to let you in on a little secret - when you want to feel your most self-assured - wear your best hat - it works like a charm, without fail, every single time! Our top dating tip is to relax, be yourself + pick an outfit you feel comfortable + confident in! We know that picking the perfect fit for a first date can be stressful, but we also know it can be way fun! So don’t worry girl, we’ve got you covered ; ) 


couple wearing brown wool fedora and brown beanie

We have put together our top 10 looks that you can pull right out of your closet for a coffee date at any time of the year. We wanted to create these looks to go with the staple pieces that all women will have in her wardrobe – like jeans, blazers + your go-to basic tees. Let’s move onto the looks you’ll love to match with your growing hat collection!  



Autumn Coffee Date Outfit 


The Ty Off-White felt hat is perfect for a cloudy day when you want to dress up + make a good first impression. Getting dressed in Autumn is one of the most exciting times of the year because you can pair warm-weather layers with cold, allowing you to wear all of your favorites from any season.  

Incorporate your accessories into the mix. Gold earrings + chunky boots are definitely statement makers… but in a subtle way that will still definitely leave you turning heads.








 Winter Coffee Date Outfit




 The Ezra keeps you looking put together while still being comfy as heck! The crown is fit for a cowgirl if that’s the look you’re going for - but don’t be afraid to pair your western-style hat with any kind of outfit you want. The cozy socks + sweater set will keep you warm on a cold winter day, while the booties add the perfect touch to complete the look.

Wintertime is the quintessential season for neutrals - from off-white felt hats to darker shades of tan. The muted hues in your wardrobe will pop against the dimness that winter brings - making your lighter outfits a great match for the season - + will camouflage your coffee spill.






Coffee Date Outfit for Summer




The Bre is ideal for the flower-picking, angelic, easy-going girl. The lightness of the straw allows for a cool head while the wide brim blocks the sun from your eyes, or if you have cute sunglasses for that, the brim sits just right to where there’s plenty of room. 

This ensemble is the definition of summer. The breezy dress and straw hat combo ensures that you're ready to hit the beach after you finish your iced coffee. 






Coffee Date Outfit With the Lieutenant Cap

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This coffee date outfit is perfect for the businesswoman that has to run back to the office after a quick date. The best outfits allow you to accomplish several things in a day, no matter how diverse your schedule may be. You can be dressed up with your preferred blazer, but remain cute + casual with your light pencil jean. 

The blazer + booties make this look feel so put together. Wearing the lieutenant cap adds a bit of trendy-ness that’s guaranteed to be a great eye-catcher.





Casual Coffee Date Outfit


outfit idea
The sound your puffy corduroy coat makes as it’s swishing against itself is so satisfying for some reason, right? Mmm. It not only sounds amazing, but it also gives you that cool girl look when paired with a cozy beanie. 

Our pick for the casual coffee date outfit is a play on the classic white t and jeans. the tan and white color scheme keeps you looking casual and cool. this fit is perfect for fall days that can get a bit chilly and require a warm coat + a knit hat that fits you best, the pip beanie. 







Coffee Date Outfit With the Ginger


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The ginger - cinnamon is a summer statement maker! The Ginger has that rich color + high-end wool that may be considered a cold-weather hat only, but you can truly wear this one all year round.  

Although simple, this outfit has bold pieces. It is perfect for when you want to make a big impression on your date and really showcase your personality + sense of style.






Coffee Date Outfit for Spring


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See what we mean when we say that putting together coffee date outfits can be so much fun? Spring is pretty much made for a broken-in pair of Birkenstocks + a beautiful straw hat with a chin strap. 

The Aiden is easy, breezy + beachy. This linen set and straw hat are ready for a spring coffee date! adding the woven bag and gold accessories finish off the look + complement the laid-back style.







Coffee Date Outfit With the Cara Loren

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This ensemble will never go out of style with classic garments that every woman has lying around at home + it was made for a rainy day coffee date. glasses + a flannel are coffee shop attire go to’s for dates or grabbin’ a cappuccino while you're out with the girls. 

The fuzzy booties up the coziness of this fit. And of course,  no outfit would be complete without a sophisticated fedora hat! we added our Cara Loren hat in tan to complete the look.






Coffee Date Outfit With the Dakota



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 This is the ultimate city girl look + as you can tell, those boots are made for walkin’ through all of the most exciting downtown streets!  This combo is perfect for a coffee date. there's no better way to enjoy a pumpkin spice latte than in those black booties. Obsessed with this look because it goes so well with our gorgeous triangle crown.

The cream Dakota felt hat adds the perfect amount of fall ~vibes~ + the leather tote bag tops everything off!







Coffee Date Outfit With the Billie

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Our tenth + final coffee date outfit pick has plenty of layers to keep you warm during cold winter storms. If it’s especially blizzardy outside, you’ll have your thick soles to keep your toes safe + your premium wool hat to stay toasty. 

If you need a little more warmth, don’t be scared to snuggle up to your date - if they’re worth it + they smell good ; ). This outfit has a minimal color scheme that feels very sophisticated and trendy. the classy tall crown Billie hat is the perfect addition to elevate your look!





Whether you want to go in for a kiss at the end of the night, or run in the opposite direction as fast as possible (only time will tell) - you're gonna look cute doing it either way. But, more importantly, you’ll feel confident in everything you decide to wear!  xx