Date nights are important to have all year round. But there’s something about dates in the fall that are so much fun. The cold weather is perfect for cozy date nights and spending time with your significant other. Some fun date-night activities in the fall might include going to the apple orchard, having lunch at a winery, going on hikes to look at all the fall leaves or simply trying a new restaurant. You also want to feel confident, look your best and be comfortable all night long. So I’m rounding up my favorite fall date night outfits from casual, fancy and everything in between.

For more fall outfit ideas, you’ll love this post too where I share over 25 fall outfits.

Fall Date Night Outfits

Dresses for Fancier Date Nights

fall fancy date night outfits

A fancy date night out is good for the soul. Though Tim and I don’t get to sneak away as often now that we have Josie girl, it’s fun to do every once in a while. I love pairing either a maxi, midi or mini dress with booties or knee-high boots for an elevated look. You can also pair a braided heel like these with a dress. Floral patterns with deep fall tones are on-trend this season, and are so easy and comfortable to wear. These looks would be perfect if you’re going to a nice restaurant or to a theater to see a play or musical. Finish the look with a felt fedora and a small handbag to carry your essentials.

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Mini Skirt with a Sweater or Ruana

fall date night outfits - Mini Skirt with a Sweater or Ruana

Faux leather skirts are a great alternative to wearing a dress on a fall date night. Leather and suede are two materials that you see a lot of throughout the fall season, and I love incorporating those materials in the skirts I wear. Try pairing the skirt with a chunky sweater and simply front tuck the sweater into the skirt. To give your legs a bit more coverage and to avoid wearing tights, finish the look with the over-the-knee boots. Some date night ideas you could wear this look to are a comedy show, concert or to a trendy restaurant.

For date night hair, I like to keep it simple with loose, natural-looking curls. I love using my Dyson Airwrap curling attachment to get a blowout look. It dries your hair fast without using a ton of heat, but I also love to use it on dry hair as well!

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Mini Skirt with a Sweater or Ruana


Another fun way to style a faux leather skirt is to layer a ruana over long sleeves, like this tee bodysuit. You could also layer the tee with a denim jacket. I like wearing layers in the fall because it can sometime be warm one minute and cool the next, depending on where you live. Finish the look with knee-high boots and a neutral lip. I keep it pretty neutral with my lipsticks most of the time. My favorite lipstick is this one. It’s a great neutral color that you can wear throughout the season.

Jeans with Booties for a Casual Date

For a more casual date, pair straight leg jeans with a cardigan or kimono. I like wearing a bodysuit underneath a kimono or cardigan. Since the cardigan is loose-fitting, a bodysuit balances out the look. Also, don’t be afraid to wear white jeans in the fall. I talk all about my love wearing them all season long in this post here. You could also wear a sweater blazer or leather jacket instead of a cardigan for a dressier date outfit while still wearing jeans. If you’re going to pick apples or pumpkins, catch a movie or do a casual dinner, both these looks would work well.

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Leggings with an Oversized Sweater

fall date night outfits

It wouldn’t be fall if we didn’t talk about faux leather leggings. These are so versatile to wear throughout the season, and can easily be dressed up or down. They come in petite, regular and tall lengths for a customized fit too. I like wearing an oversized sweater and knee-high or over-the-knee boots with the leggings. You could also pair with a button up shirt or a plaid tunic and wear mules instead of boots. This outfit is slightly casual and slightly dressy, so I think you could wear this to a variety of date nights. It would also be a great fall-party outfit.

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Do you have a fun date night idea for the fall? Let me know in the comments below!

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fall date night outfits


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