10 Fall Date Night Outfit Ideas to Try this Fall

Is there any better time of year for a night out? From crisp air to hearty dishes and creative seasonal cocktails, what’s not to love about getting out on the town in fall. Here’s a classy fall date outfit I wore recently—at the bottom of the post I share 10 more fall date night outfit ideas for every type of outing.

Timeless Sweater

Statement tops aren’t just for summer. I love oversized sweaters during the day but prefer a fitted sweater with feminine detail (similar under $150 here) for evenings. The elongated cuffs on this turtleneck make for easy dining without worry of spills! Warm up by layering a blazer or cardigan coat overtop.

Fall Date Night Outfit

Midi Skirt

I love a skirt and tucked sweater combo. If the sweater has more body, a skirt can help accentuate the waist. This wool one is a classic I recently invested in, but I love this evergreen satin skirt (perfect for the holidays), this gorgeous cream midi, and this unique patterned find (under $30).

Knee-High Boots

If you want a boot that doesn’t break the bank, look no further: these black knee-highs are so comfortable and I found them on Amazon! I have athletic legs, for reference, and they’re neither too tight nor too loose on my calves.


My classic everyday jewelry transitions well to nighttime. I wear rings and earrings with a sweater—a necklace might detract from the roll neck detail.

10 Fall Date Night Outfit Ideas

Dressy fall date night outfit

For a Dressy Vibe:

  1. Maxi dress or midi dress + knee-high boots + leather jacket 
  2. Long sleeve jumpsuit + heels
  3. Leopard print mini dress + over-the-knee boots
casual fall date night outfit

For a Casual Vibe:

  1. Nordstrom sweater dress + over-the-knee boots
  2. Trench coat + off-the-shoulder blouse + ankle jeans + booties
  3. Faux leather leggings or leather pants + oversized sweater + booties
  4. Cable sweater + slip dress + suede booties

For an Activity:

  1. Topshop puffer jacket or denim jacket + Graphic tee + pair of jeans + sneakers
  2. Classic button down t-shirt + high-waisted skinny jeans + loafers
  3. Oversized sweater or graphic sweatshirt + ankle jeans + cozy boots

What’s your go-to fall date night look? I’m dedicated to my sweater and skirt combination, but I love denim with a blouse and booties, too. I’d love to hear your thoughts and suggestions in the comments or on Instagram! For more fall date outfit inspiration, visit my Pinterest boards.