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Cute Fall Date Ideas + What to Wear

cute fall date ideas and what to wear

Searching for fun fall dates for couples? We’ve put together a guide of cute fall date ideas AND what to wear for each destination! From what to wear to the pumpkin patch to what to wear to the farmer’s market, we’ve got all the fits and fun fall date ideas in one place! 

Pumpkin Patch 

what to wear to a pumpkin patch

Shop Shackets 

If you’ve got a pumpkin patch near you, this is the perfect fall date idea for you and your significant other. Layering any outfit with a shacket will have your fall outfits fit for the pumpkin patch. 

Farmer’s Market 

what to wear to farmer's market

Plaid blouses 

A casual Saturday stroll through the local Farmer’s Market is an easy date idea. Explore local vendors while wearing our favorite fall print – plaid! Plaid blouses are so easy to dress up or down with denim or leggings. 


what to wear on a hayride

Fall Graphic Tees 

Who doesn’t love a hayride in the fall? Grab your favorite fall graphic tee for this go-to fall outing. 

Vineyard + Wine Tasting

outfits for wine tasting

Shop Dresses 

There’s something beautiful about going to a winery in the fall! We love to dress up in these instant outfits particularly in our favorite fall hues: burgundy, camel, and olive. 


hiking outfits

Shop Leggings

Hiking dates are so great for conversations! Throw on a graphic sweatshirt and leggings combination for those cool fall afternoons. 

Cooking Class 

casual dresses

Shop Dresses 

A new take on a dinner date! Taking a cooking class is a fun experience and you get a great meal too. Think comfy, casual fall dresses for the occasion. Throw on white sneakers to finish the look. 

Haunted House 

halloween graphic tees

Halloween Graphics

Also a great group date idea, our collection of Halloween Graphic tees will give you lots of outfit options for what to wear to a haunted house. 

Bonfire & S’mores 

fall cardigans

Shop Cardigans

Bonfire nights in the fall are core memories! Grab a cardigan for a layered look while you’re making s’mores. Set up a projector for a cozy movie night as well! 

Horseback Riding 

horseback riding outfits

Shop Jackets

Horseback riding is a great fall date idea and can certainly be an adventure! Layer a shacket with some western style boots and jeans to make sure you’re dressed appropriately for the date while also looking super cute! 

Local Coffee Shop 

fall graphic tees

Shop Tees

A low key but still great date is an afternoon date to your local coffee shop. A trendy outfit option is biker shorts styled with an oversized graphic tee.

Looking for more fall event outfit inspo? Check out our Style Guide.

outfits for every fall occasion