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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.
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.
shop similar: button-down | skirt | boots
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.
shop similar: dress | hat | boots
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!
shop similar: tee | skirt | boots
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.
shop similar: top | skirt | heels
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.
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.
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.
shop similar: sweater | jacket | jeans | boots
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.
shop similar: dress | hat | boots
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.
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!
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!
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.
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!
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.
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!
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.
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? 😉
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!
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.
shop similar: turtleneck | dress | heels | bag
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!
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.
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!
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!
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.
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.
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.
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!
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!
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.
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.
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.
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!
shop similar: tee | coat | skirt | heels
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!
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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!
shop similar: tee | blazer | jeans | hat | heels
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!
