15 Fall Date Outfits 

Fall is one of my favorite seasons for date nights. There’s something about the crisp air and changing leaves that makes everything feel a little more romantic. And let’s be honest—fall fashion is unbeatable. From cozy layers to stylish boots, there are endless ways to create a date outfit that’s both cute and practical for the cooler weather.

But sometimes, it can be tricky to figure out what to wear for different types of fall dates. Whether it’s a casual coffee date, a fun outdoor adventure, or a more formal dinner, the right outfit sets the tone for a perfect evening. 

I always think about the balance between looking good and feeling comfortable, especially with fall’s unpredictable weather. That’s why I’ve put together these 15 fall date outfits to help you find the perfect look for your next romantic outing!

1. Sweater and Jeans Combo

You can never go wrong with a classic sweater and jeans. It’s comfortable and versatile for any casual fall date. Pair it with ankle boots for a cozy but stylish look.

2. Leather Jacket and Skirt

A leather jacket adds a bit of edge to your fall date outfit. Pair it with a cute skirt and some tights for an effortlessly cool vibe. Finish the look with heeled boots to add a touch of chic.

3. Flannel Shirt and Skinny Jeans

For a laid-back fall date, a flannel shirt is the way to go. It’s cozy and gives off that perfect autumn vibe. Pair it with skinny jeans and booties for a comfortable and stylish look.

4. Turtleneck and Midi Skirt

A turtleneck is a fall staple, and when paired with a flowy midi skirt, it creates an elegant yet relaxed date outfit. Add a belt to cinch the waist and complete the look with ankle boots.

5. Knit Dress and Knee-High Boots

A knit dress is both cozy and stylish, making it perfect for fall date nights. Pair it with knee-high boots to elevate the look while staying warm. Add a long coat or scarf for extra layers if it’s chilly.

6. Trench Coat and Jeans

A classic trench coat is a must-have for fall. Layer it over a simple blouse and jeans for a polished yet laid-back date outfit. Finish the look with loafers or booties for added sophistication.

7. Plaid Blazer and Trousers

Plaid is the ultimate fall print, and a plaid blazer instantly adds style to any outfit. Pair it with tailored trousers and heeled ankle boots for a chic yet professional look—perfect for a more formal date night.

8. Chunky Sweater and Pleated Skirt

A chunky sweater paired with a pleated skirt creates the perfect balance of cozy and cute. This outfit is great for an afternoon date or a casual dinner. Add tights and boots to stay warm while still looking stylish.

9. Denim Jacket and Dress

For a casual yet feminine look, layer a denim jacket over a cute fall dress. This is perfect for an outdoor date or a weekend outing. Pair it with sneakers or ankle boots for an easy, laid-back style.

10. Cardigan and Slip Dress

A cardigan layered over a slip dress is a great fall date night option. It’s both cozy and romantic, especially when paired with strappy heels or boots. Add a statement necklace to complete the look.

11. Peacoat and High-Waisted Pants

A peacoat is a stylish way to layer for fall. Pair it with high-waisted pants and a fitted turtleneck for a sophisticated and timeless look. Add loafers or heeled boots to keep the outfit polished.

12. Scarf and Jeans Combo

For a simple yet stylish fall date outfit, throw on a cozy scarf with your favorite pair of jeans. Layer it over a long-sleeve top or sweater, and finish with ankle boots or sneakers for an effortlessly cool look.

13. Sweater Dress and Tights

A sweater dress paired with tights is perfect for a more casual fall date. It’s cozy, warm, and easy to dress up or down depending on the occasion. Add a statement belt and knee-high boots for a touch of sophistication.

14. Poncho and Leggings

A poncho is a unique and cozy option for fall. Pair it with leggings for an ultra-comfortable look that’s still stylish. Complete the outfit with knee-high boots or ankle boots for a date night that’s both fashionable and functional.

15. Button-Up Shirt and Midi Skirt

For a more elegant fall date, a button-up shirt tucked into a midi skirt is a classic combination. It’s polished and feminine, perfect for a dinner date or evening outing. Add heels and delicate jewelry to complete the look.