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March 07, 2022 5 min read


What to Wear for a Coffee Date

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 wanted to create these 10 coffee date outfit ideasto go with the staple pieces that all women will have intheir wardrobe – like jeans, blazers + your go-to basic tees. Let’s moveon tothe looks you’ll love to match with your growing hat collection!


What to Wear on a Coffee Date by Season

To help you put together the perfect coffee date outfit, we've created 4 different outfit ideas based on the current season. Whether you're looking for something casual and comfortable or elegant and sophisticated, our outfit ideas will inspire you to create a look that perfectly reflects your personal style and pairs well with your favorite Gigi Pip hat. 



A black turtleneck sweater, gold earrings, plaid skirt, chunky boots, and the TY in off white as an autumn coffee date outfit idea.
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.



A tote bag, sweater set, booties, cozy socks, and the Tan Ezra as a winter coffee date outfit idea

 The Ezrakeeps 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.



A linen set, slip on sandals, woven bag, gold earrings, and the Aiden in Natural as a springtime coffee date outfit idea.

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.



A floral dress, statement earrings, lace up sandals, pearl purse, and the Bre in Natural as a summertime coffee date outfit idea

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 havecute 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 ensure that you're ready to hit the beach after you finish your iced coffee. 


What to Wear on a Coffee Date by Hat Style 

At Gigi Pip, we believe that hats are a powerful accessory that can take your outfit to the next level. To help you make the most of our hats, we've put together several outfit ideas that are perfect to wear on a coffee date and feature some of our favorite Gigi Pip hats.



A linen set, slip on sandals, woven bag, gold earrings, and the Aiden in Natural as a springtime coffee date outfit idea

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.




A white shirt, levi jeans, corduroy puffer, white sneakers, and a Gigi Pip beanie as a coffee date 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. 



A black tank top, black leather belt, white trousers, sunglasses, platform sandals, and The Ginger in cinnamon as a coffee date outfit idea.


The Ginger - cinnamon is a summer statement maker!The Ginger has that rich color + high-end woolthat 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 reallyshowcase your personality + sense of style.



A Plaid overcoat, glasses, black jeans, tan booties, and The Cara Loren in Tan make a great coffee date outfit.
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 asophisticated fedora hat! We added our Cara Loren hat in tan to complete the look.



A ribbed tank, tote bag, patterned pants, black booties, and the Gigi Pip Dakota Hat in a Cream color make a great coffee date outfit.
 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 apumpkin spice latte than in those black booties.Obsessed with this look because it goes so well with ourgorgeous triangle crown.
The cream Dakota felt hat adds the perfect amount of fall ~vibes~ + the leather tote bag tops everything off!


A black turtleneck, sweater vest, tan trousers, black loafers, and the Billie in Ivory are a great coffee date outfit.


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 + yourpremium 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 + theysmell good. This outfit has a minimal color scheme that feels very sophisticated and trendy. theclassy 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