Date Night: 5 Fall Outfits For A Night Out

I don’t know about you guys, but I feel like fall clothing is perfectΒ for dressing up and getting fancy. From the dark red lipsticks to the tall boots, it’s finally easy to look nice! Summer is always tricky for me, because I can’t wear shorts to work (too much AC) but I can never find nice dressy capris. Once the weather gets a bit colder, I bring out all of my boots and sweaters and I get to wear a whole new wardrobe.Β 

These new looks make date night so much fun. I love going out on the town with Kyle, even if we keep it pretty low key with a night at the movies. Like everyone, I love to look nice but I want to be comfortable at all times too. Many of my outfits are pretty versatile, and would transition from day to night easily. Here’s some outfit inspiration for your next date night!


I had this jacket on my Fall Wishlist, and if you’ve been keeping up with me lately, than you probably saw these flats on my Shoe Wishlist as well. I finally got the jacket, but I’m still dying to get these flats. Skinny jeans and a nice top are often my go-to for work and play, but I really like the way this outfit and sophisticated but still fun at the same time.

I found this top at GAP and it’s so soft and flattering; I feel really confident wearing it, even if it’s paired with just jeans. The big necklace ties the outfit together, and the flats give it a nice pop of color. I would definitely wear this out to dinner, or to play pool with friends.


Flannels are definitely a Fall favorite, and I wear them somewhat regularly during the year as well. If I’m spending the day inside cleaning or catching up on my shows, than I love to pair them with some leggings. But for a night out you can dress them up with these little booties and a cute scarf.

There are so many colors to choose from when it comes to flannels, but I’m loving the reds and greens this season. And there are tons of different lengths to choose from, making it easy to throw on some leggings or tights and a skinny belt for a more dressy look.


I have a huge collection of long sheer blouses for work, and they’re definitely my go-to for a sophisticated but comfortable look. We aren’t quite into the season enough to need multiple layers, but I definitely need some long sleeve options. As always, I love the pop of red in this blouse, but you can find these in so many colors at H&M and Forever XXI.

For this outfit, I like the idea of wearing some black tights, either regular or fleece lined. Make sure that it’s a long blouse, meaning it’s basically a dress. If it’s not long enough to be at your mid thigh, than stick with leggings. The flats have a nice little detail on them to add a little something to this simple look. I would wear this out to dinner, but it’s versatile enough to wear anywhere really.


This is my favorite outfit for the colder parts of fall. I love pairing huge sweaters with a cute scarf, and throwing on some boots. They don’t have to be the tall boots either. If you prefer Uggs or flats, either would look great. I would wear this to complete some of my Fall Bucketlist activities, like going to a corn maze or a haunted house!

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I’m a big fan of colored jeans, and American Eagle has some great options. I have about 4 different pairs, and they’re the perfect addition to any outfit. I have a few sweater cardigans as well, but I’m still looking for the perfect sleeveless one. Pair it up with a deep red lip and some pretty earrings, and this would be the perfect outfit for a holiday party or a fall photoshoot.

What are your favorite fall outfits?

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23 thoughts on “Date Night: 5 Fall Outfits For A Night Out

  1. Love all of these outfits! Especially liking the outfit with the blush colored sweater. It will look so cute and looks like it will be very comfortable as well! Win Win!!

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  2. I love all of these! I hate that it is winter before I can wear clothes for cooler weather. I can so ready to wear cute fall clothes like this!

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  3. Oh the first and last two are my favorite but I’d wear all of these. I love fall dates and dressing up, I usually do a dress, tights and heels. Boring and simple.

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