fall date night outfit

46 Super Stylish Date Night Outfits to Wear This Fall

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Transitioning from one season to another can be hard enough, but trying to figure out what to wear for a date in the new season when you haven’t fully established your seasonal wardrobe sounds like a nightmare! Lucky for you, we’ve put together over 40 outfits that will work for a variety of occasions. Scroll through to gather some fall date outfit inspiration!

1. high-waisted wide leg pants + crop top + moto jacket + heels

Nothing says “chic fall date outfit” like an all-black outfit! This classic ensemble will have you feeling like a million bucks, which is exactly how you should feel on date night! Mixing a crop top with a jacket will keep you warm, but also allow you to show off just a bit of skin. The moto jacket will also provide a sense of edginess, while the heels add a touch of femininity.

fall date outfits

shop similar: top | moto jacket | pants | heels

2. white button down + camel skirt + over-the-knee boots

A classic staple, the white button-down, is a great piece all year round, but really gets its chance to shine in the fall. The possibilities are endless! Pairing it with a skirt and tall boots is a simple outfit that requires little effort on your part, but looks polished and put together! When you’re rushing to find something to wear and get out the door, this combination will never steer you wrong. If you need a little extra warmth, a blazer or long coat would be a great addition.

fall date outfits

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3. black dress + hat + over-the-knee boots

A little black dress is something every woman should have in their wardrobe and date night is the perfect time to bring it out! In the summer, you may wear strappy sandals or heels, but when transitioning to fall, over-the-knee boots are a great footwear option. They keep the majority of your legs covered, but still allow for a little skin to show.

fall date outfits

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4. black tee + camel skirt + ankle boots

Elevate your basic tee by pairing it with a skirt and ankle boots. This combination is great for a more casual date night, but could easily be dressed up with a blazer or trench coat!

fall date outfits

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5. wrap top + bodycon midi skirt + heels

A form-fitting shirt paired with a tight skirt might scare some people, but here’s why it shouldn’t. A wrap top is going to help draw your waist in and create an hourglass look, while the skirt is going to accentuate your natural curves and show off your beautiful body. Plus, the heels are going to help elongate your legs and give you a little lift, if you know what I mean. 😉 To complete this look, add a long coat to provide a bit of warmth.

fall date outfits

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6. long sleeve tee + animal print skirt + hat + knee-high boots

If you love an all-black outfit but want to switch it up a bit, this outfit is for you. Pairing a black top with an animal print skirt keeps the neutral aspect that you love while also adding a bit of boldness to your look.

fall date outfits

shop similar: top | skirt | hat | boots

7. black tee + black jeans + moto jacket + hat + over-the-knee boot

This combination is a perfect fall date night outfit for a few reasons. Not only will it keep you warm in the cool weather, but the all-black base also creates a sophisticated look. Adding in the moto jacket adds a bit of warmth, embracing the fall season.

fall date outfits

shop similar: tee | jeans | jacket | hat | boots

8. sweater + jacket + moto jacket + black jeans + ankle boots

This is another great option if you’re looking for an elevated casual look. Plus, it can easily be dressed up or down, depending on your date night plan.

fall date outfits

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9. sweater dress + hat + over-the-knee boots

Not only are sweater dresses incredibly flattering, but when paired with tall boots, they are ultra-chic. Stay warm and look your best with this outfit combination.

fall date outfits

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10. striped shirt + leggings + scarf + over-the-knee boots

Going to the pumpkin patch or apple picking? Here’s an outfit for you! Elevate your basic tee and leggings with a scarf and boots – you don’t have to sacrifice comfort for style! It’s all about balance.

fall date outfits

shop similar: tee | leggings | scarf | boots

11. sweater + denim skirt + tights + silk scarf + hat + ankle boots

When the weather starts getting cooler, don’t pack away all your summer items! Instead, incorporate them into your fall wardrobe by adding layers. In this case, wear tights and boots with your denim skirt to keep this classic piece functional all year long! Pair with a sweater and scarf and you’re good to go!

fall date outfits

shop similar: sweater | skirt | tights | scarf | hat | boots

12. tunic sweater + leather leggings + heels

Pairing a tunic sweater with leggings is great for not only warmth but comfort as well! This look could be dressed down, but can easily be elevated with the right accessories. Heels pair great with this to perfect your date night look!

fall date outfits

shop similar: sweater | leggings | heels

13. graphic tee + fringe jacket + plaid skirt + hat + over-the-knee boots

Looking for the perfect chic fall outfit? Here it is! There may seem to be a lot of patterns/textures, but they balance so well together.

fall date outfits

shop similar: tee | jacket | skirt | hat | boots

14. tee + denim jacket + moto jacket + skinny jeans + heels

Easily go from day-to-date-night with this outfit combination. Adding a moto jacket over a denim jacket not only adds warmth but depth and interest to your outfit as well! Trade out your day shoes for a pair of heels and you’re date night ready!

fall date outfits

shop similar: tee | denim jacket | moto jacket | jeans | heels

15. graphic tee + blazer + leather leggings + hat + leopard ankle boots + sunglasses

This is another option that’s easily transitioned from day to night. Pairing a sophisticated piece like a blazer with a casual graphic tee creates a great balance in your outfit. The leather leggings are a great addition to really elevate the outfit and add a bit of edginess to your look.

fall date outfits

shop similar: tee | blazer | leggings | hat | boots | sunglasses

16. black dress + blazer + hat + leather boots

Adding a blazer over your dress will help bring back a little shape to your figure, while also keeping you protected from the elements. Slip on your favorite leather boots to add warmth to your look, both literally and figuratively!

fall date outfits

shop similar: dress | blazer | hat | boots

17. tee + cardigan + mini skirt + tights + over-the-knee boots

Fall weather can be confusing. It’s brisk in the morning, warms up in the afternoon, and then cools back down as the evening comes. Figuring out what to wear can be challenging! To make your transition seamless, wear your classic summer staples with layers that can easily be removed. If you get warm, simply slip off your top layer and you’re good to go.

fall date outfits

shop similar: tee | cardigan | skirt | tights | boots

18. striped tee + sweater + moto jacket + mini skirt + leather boots

If there’s one thing that is synonymous with fall when it comes to fashion, it’s layers! Not only is it practical in the cooler weather, but it adds so much interest to your outfit. Plus, if you layer more on the top, you can sacrifice on the bottom to show a little skin, right? 😉

fall date outfits

shop similar: tee | sweater | jacket | skirt | boots

19. white button-down + moto jacket + black jeans + combat boots + sunglasses

This combination gives model-off-duty vibes in the best way! You’ll feel like the coolest girl in the room while wearing this. Want to elevate it even more? Add a bold red lip!

fall date outfits

shop similar: button-down | jacket | jeans | boots | sunglasses

20. turtleneck + leopard slip dress + heels + clutch

Opposite of the previous outfit, this look is soft and delicate. The turtleneck provides coverage and the dress adds boldness without being overwhelming. Pairing these with a light pair of heels helps soften the look, making it perfect for a sweet date with your loved one this fall.

fall date outfits

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21. white tee + moto jacket + black jeans + combat boots

If there’s one thing you add to your fall wardrobe this year, consider the moto jacket! It’s very practical in the colder months and is versatile enough for any outfit. Add your moto jacket over the simplest of outfits and you instantly get an upgrade!

fall date outfits

shop similar: tee | jacket | jeans | boots

22. tweed dress + hat + over-the-knee boots

How cozy is this look?! The dress and boot combination is perfect for the weather, and the fun accessories such as the hat add a unique twist that is perfect for any fall date night.

fall date outfits

shop similar: dress | hat | boots

23. silk cami + moto jacket + black jeans + heels

Like we’ve said before, you can never go wrong with an all-black outfit! Add your ever-so-loved moto jacket and a pair of heels and you’re sure to steal the show wherever you go!

fall date outfits

shop similar: cami | jacket | jeans | heels

24. black tank + tweed blazer & shorts + block heels

If it’s still fairly warm where you are, here’s an adorable date night outfit for you! This tweed set is perfect for fall – the colors and textures are beautiful, and the blazer adds a little bit of warmth. Pair with some block heels and you’re oh-so-chic!

fall date outfits

shop similar: tank | blazer & shorts | heels

25. black dress + leopard blazer + ankle boots

Feeling uninspired with what to wear but want to wear something that looks like you put in a lot of effort? Pairing a bold print blazer with a black dress brings a little bit of excitement to your look and all you have to do is put it on! Slip on some ankle boots to complete your fall ensemble.

fall date outfits

shop similar: dress | blazer | boots

26. white button down + striped sweater + skirt + leather boots

While a button-down shirt and pencil skirt may be thought of as “office attire”, these pieces can easily be worn for date night too. Tying a sweater around your neck adds a bit of a preppy twist to your look, but will come in handy if you get chilly throughout the evening. Grab your leather boots and you’re ready to go.

fall date outfits

shop similar: button-down | sweater | skirt | boots

27. black dress + ankle boots

Another all-black look, can you tell we love it? 😉 You seriously can’t go wrong! If you need extra warmth, try adding a trench coat or a pair of tights.

shop similar: dress | boots

28. houndstooth dress + blazer + leather boots

Embrace the fall season with a houndstooth print dress! Add a blazer for structure and tights for a bit of extra coziness. Your trusty leather boots are the perfect addition to complete this look!

fall date outfits

shop similar: dress | blazer | boots

29. striped tee + blanket scarf or cardigan + denim skirt + combat boots

Here’s another great example of taking your summer clothes and transitioning them into the next season. Take a basic tee and denim skirt, two classic favorites, and add a chunky cardigan to help ease into the cooler weather. Combat boots will give the look an edgy appearance, but if that’s not what you’re going for, ankle boots work great too!

fall date outfits

shop similar: tee | cardigan | skirt | hat | boots

30. cardigan + leather shorts + tights + slingback heels

Mixing textures is really fun in the colder months – it’s cozy and collected all at the same time. A boucle cardigan paired with leather shorts seems like it shouldn’t work, but as you can see here, it’s so chic! Add some tights to offer your legs a bit more protection, and slingback heels are a great footwear option.

fall date outfits

shop similar: cardigan | shorts | tights | heels

31. chambray shirt + animal print skirt + ankle boots

Wearing bold prints is all about balance, and when done correctly, you create a beautiful ensemble that’s ready to be shown off! A chambray shirt can easily be dressed up with a bold animal print skirt. Pair this combination with a pair of ankle boots for a look that is sure to impress.

fall date outfits

shop similar: shirt | skirt | boots

32. cardigan + leather pants + heels

Date night is a perfect time to step out of your comfort zone, so why not do that with your outfit as well? Add a cardigan with a pair of leather pants! You might not have thought of this combination on your own, but we can assure you that it works. Slip on your heels and throw on some gold accessories to complete this look.

fall date outfits

shop similar: cardigan | leather pants | heels

33. graphic tee + animal print coat + skirt + heels

Your graphic tees don’t need to be saved only for casual outfits. Why not dress them up a bit? Put one on under a fun animal print coat and you’ve created a bold, chic look with little effort. To keep the bold look going, add a leather skirt and your favorite heels!

fall date outfits

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34. long-sleeved tee + plaid skirt + beret + over-the-knee boots

Embrace your inner French girl with this fall date night option. A black tee pairs beautifully with a fall-colored skirt, and we love the balance of a skirt with tall boots. What really makes this look is the accessories – a beret and sunglasses add the perfect Parisian touch!

fall date outfits

shop similar: tee | skirt | beret | boots

35. graphic tee + animal print blazer + denim skirt + hat + ankle boots

Here’s another example of adding a graphic tee with a bold blazer to create a sophisticated look. This option is a little more casual than the first one, swapping the leather skirt for a denim one.

fall date outfits

shop similar: tee | blazer | skirt | hat | boots

36. white button-down + camel skirt + scarf + over-the-knee boots

We’ve seen this look already as well, but how fun is it with a scarf? It’s amazing how much accessories can change an outfit.

fall date outfits

shop similar: button-down | skirt | scarf | boots

37. polka-dot blouse + camel coat + leather leggings + ankle boots

What’s up next? You guessed it! Another black outfit! 😉 This one is great because the patterned top adds a little something extra.

fall date outfits

shop similar: blouse | coat | leggings | boots

38. mini dress + trench coat + silk scarf + hat + over-the-knee boots

If you’re looking to stay warm, but don’t want to sacrifice a good outfit, here you go! With the trench coat being the focal point, you don’t have to worry about whether your outerwear distracts from what you’re actually wearing. The tall boots keep the allure of showing a bit of skin and the accessories complete the look by adding a chic touch.

fall date outfits

shop similar: dress | coat | scarf | hat | boots

39. white button-down + maxi skirt + belt + heels

Traditionally fall brings out the deep, dark colors, but who’s to say you can’t be bold too?! Go out of your comfort zone and wear a bright skirt this season, perfectly paired with a button-down and heels.

fall date outfits

shop similar: button-down | skirt | belt | heels

40. black tank + long cardigan + leather pants + heels

This look will ensure you look sophisticated while keeping you comfortable at the same time! No matter what activity you have planned, this is a great date night look.

fall date outfits

shop similar: tank | cardigan | pants | heels

41. black dress + black blazer + block heels

If you love the all-black look but want to break it up a bit, swap out the shoes! A neutral shoe will help elongate your legs, and these two-toned heels are so chic.

fall date outfits

shop similar: dress | blazer | heels

42. sweater dress + animal print boots

Pairing a simple sweater dress with a bold pair of ankle boots is an easy way to elevate your outfit this fall season! A trench coat would be a great addition if you needed a little extra warmth.

fall date outfits

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43. striped tee + suede skirt + hat + over-the-knee boots

Here’s another great option for those of you who want to embrace autumn but don’t quite have the cool weather to match. Bringing in those warm fall colors will help make any outfit fit in with the season, even if it contains summer pieces! Adding tall boots and a hat round out your look and draw in those “fall vibes” as well.

fall date outfits

shop similar: tee | skirt | hat | boots

44. black slip dress + heels

You truly can’t go wrong with this classic look. While it might not work on its own for a fall date night, adding a long camel coat or a blazer would keep you warm without taking away from the simple beauty of this outfit.

fall date outfits

shop similar: dress | heels

45. graphic sweatshirt + skirt + over-the-knee boots

Elevate your graphic sweatshirt by pairing it with a skirt and tall boots! This adds a fun, girly touch to your outfit, while still keeping you warm and covered.

fall date outfits

shop similar: sweatshirt | skirt | boots

46. black tee + red coat + camel skirt + over-the-knee boots

Again, who says you can’t wear bold colors in the fall?! Take this neutral outfit, black tee and a camel skirt, and add a pop of color with a red coat! Pair with tall boots and you’re ready to take on the night.

fall date outfits

shop similar: tee | coat | skirt | boots

47. black tee + camel blazer + flare jeans + hat + heels

Dress up your basics by adding sophisticated pieces to your look. Start with a black tee and jeans and build on that. Add a blazer for warmth and structure, and putting on a pair of heels will dress this outfit up even more!

fall date outfits

shop similar: tee | blazer | jeans | hat | heels

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I hope this roundup of fall date outfits gave you some outfit inspiration for this fall season! Whether you’re going to the pumpkin patch, apple-picking, out for dinner, or anything in between, you’re sure to find something that works for you!

If you’re looking for more everyday fall outfits, here are 30+ outfit ideas for you to browse through!

fall outfit ideas for date night
fall date outfits


Hi, I’m Tirzah! I’m an Iowa native, raising two little girls with my high school sweetheart. I’m a lover of coffee, true crime, and of course – all things fashion! You’ll usually find me in my classic “mom uniform”, a soft, neutral top, high waisted jeans, and tan leather loafers…always with a coffee in hand!