15 Fall Date Night Outfits to Summon Autumnal Romance

You're going to fall in love with these looks (we had to).

fall date outfits

Design by Tiana Crispino

Autumn is officially here, which means it’s time to pull out our favorite sweaters, drink pumpkin spice like it’s your job, and get ready to fall in love. Whether you’re swiping through Tinder to find someone to go with on Instagramable dates or hitting the apple orchards with your long-time partner, autumn is the perfect season for cute date ideas, and even cuter fashion. Here are fifteen outfit choices for fifteen classic date ideas.

Apple Picking 

One of the classic autumnal activities, it just doesn’t feel like fall until we’ve hit the apple orchard. Apple picking is a versatile date activity for first dates and partners alike. Keep it casual with a cozy sweater and some comfy jeans to look low-key cute. 

apple picking

Design by Tiana Crispino

Cider Tasting 

cider tasting

Design by Tiana Crispino

If you want to skip the picking and go right to the tasting, hit the cidery to sample some homemade cider and get to know your date. Dress up your look with a silky skirt, bandeau, and an oversized blazer that toes the line of sexy and casual. 

Corn Maze 

corn maze

Design by Tiana Crispino

Another fall favorite is the corn maze, a perfect date night activity that can show you how well you and your date can problem-solve together (or show how long you can stand to be around each other). Embrace the cottagecore vibe of the corn maze by wearing your favorite flowy dress, but make sure you wear sneakers—you may be in there for a while.

Pumpkin Carving 

pumpkin carving

Design by Tiana Crispino

Who doesn’t love to show off their pumpkin carving skills on a first date? Look as cute as a pumpkin with some overalls, embroidered sleeve top, and a cute bandana to have a creative and fun date night.

Bookshop Date 

bookshop date

Design by Tiana Crispino

A classic first date spot becomes very popular during pumpkin spice season. Create a smart and comfy look with an oversized shirt dress, knit vest, and some cute boots to make this trend into a classic.

Haunted House 

haunted house

Design by Tiana Crispino

Indulge in the nostalgia of attending a haunted house with your sweetie this autumn and dress up for the part in your favorite Halloween shoes. Just remember to watch where you step in these witchy heels in case you need to run.

Scary Movie and Chill 

scary movie

Design by Tiana Crispino

If you want to keep your thrills at home, invite your date over for a scary movie marathon and get dressed in your nicest PJs. Just a heads up: With this matching lounge set and silky bathrobe, your date may be more focused on the “chill” instead of the movie. 



Design by Tiana Crispino

Embrace the season by bringing your date to an Oktoberfest event to enjoy beer, pretzels, and looking like a whole snack in this black mini skirt and thigh-high boots.

Taking a Hayride 

taking a hayride

Design by Tiana Crispino

If you’re already picking apples and strolling through the pumpkin patch, you might as well go all the way with a good ol’ hayride (think of the Instagram selfie!). Go for a ride with a cute all-denim jumpsuit and bring the Canadian tuxedo out to the country.



Design by Tiana Crispino

Whether you have a strong love of the game or need to be told what the rules are every quarter, tailgating can be a fun outing for a date, especially when you pair a moto jacket with some relaxed jeans and some cute boots to help your team score. 

Take a Hike

take a hike

Design by Tiana Crispino

Take in the beauty of autumn by going on a hike with your date. Enjoy the last of the warm days, see the leaves change, and look cute in your bike shorts and oversized flannel.

Farmer’s Market 

farmers market

Design by Tiana Crispino

Enjoy a nice easy date by strolling through the farmer’s market hand-in-hand with your date and enjoy the fall harvest. For a laid-back day, break out your trendy wide-leg pants, a cropped knit tank, and your oversized jacket for an effortless look. 

Road Trip

road trip

Design by Tiana Crispino

It’s officially “All Too Well (Taylor’s Version)" season, so grab your maple lattes and take a long drive getting lost on the road. Take your date on a weekend drive and watch the leaves turn while you listen to that ten-minute version of “All Too Well.”

 Fall Festival 

fall festival

Design by Tiana Crispino

The coming of fall brings the last wave of fun outdoor activities before winter hits. Take advantage by attending a fall festivals with your new date. No matter what the theme of the event is, you’ll look stunning with a simple leather jacket and knit dress combination. 

Museum Date 

museum date

Design by Tiana Crispino

When all else fails, take your date to a new exhibit at the museum and see if sparks fly. Pair a plain tee with a silky dress to make yourself look like a work of art.

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