As the weather starts to cool down, figuring out what to wear can get a little tricky.
You’re not quite ready to let go of your summer favorites, but you also want to start incorporating some cozy fall pieces.
That’s where transition outfits come in—they let you mix and match the best of both seasons.
I’ve been having fun experimenting with my wardrobe lately, finding ways to stretch out those summer styles while gradually adding in some fall layers.
So, I thought, why not share some of my favorite combinations with you?
In this post, I’ve rounded up 50 cute outfit ideas that will help you smoothly transition from summer to fall.
Trust me, you’re going to love these looks!
50 Cute Summer To Fall Transition Outfit Ideas You Will Love!
1. Black Long Sleeve + Baggy Trousers
This outfit is so chic. Simply pair a black long sleeves bodysuit with wide-leg pants and some ankle boots to get the look. This outfit is perfect for when you go on morning coffee runs.
2. Black Jeans + Cardigan + White Long Sleeves
Pair a cute long knitted cardigan with some black jeans and a white top. This outfit is perfect when the weather starts to get chillier. It is also great for students who go to college. It’s easy to put together and dress code friendly.
3. Knitted Top + Trousers + Coatigan
How cute is this look? An all white fit will look SO good during the winter but also for the fall season as well. It’s so chic and elegant. The coatigan is a great staple piece for fall because you can just throw it on when it starts to get colder during the day.
4. Cardigan + Bodysuit + Jeans
Fall is literally the best season for fashion. There are just so many options to choose from. This is another great outfit idea for fall. It’s super casual and perfect for college as well.
5. Leggings + Tank Top + Shacket
Who doesn’t love a nice shacket for fall? This is such a cute outfit idea. You probably already have these items in your closet but, if you don’t I’ll link similar ones below.
6. Black Bodysuit + Cropped Jeans
Rock this fall season with this seriously chic outfit idea. Grab a black bodysuit and pair it with cropped flared jeans and some booties. I love how simple this look is. If you want to go a step further, you can accessorize this outfit with a belt and grab a cute minimal handbag.
7. Trench Coat + Bodysuit + Dad Jeans
Wear this cute outfit while you’re sipping coffee at the coffee shop. Throw on a cute black bodysuit with a trench coat and some super cute heel booties.
8. Chunky Sweater + Black Jeans + Ankle Boots
Everybody needs a good chunky sweater for the fall. Pair it with some loose-fitted jeans, and some Doc Martens.
9. Green Knitted Cardigan + White Shirt + Jeans
Embrace the changing of the leaves with this cute knitted cardigan. Pair it with a basic white tee and some ankle boots.
10. Oversized Sweater + Skorts
Slay this cute fall outfit and turn heads. This look is perfect for a date night or brunch. Grab a cute pair of mini skorts ( shorts that kinda look like a skirt ), and pair it with an oversized sweater and pointed knee-high boots.
11. Skacket + White Bodysuit + Flare Jeans
Pair this cute fall shacket with a turtleneck bodysuit, flare jeans, and some white sneakers. You’ll be ready to go apple-picking.
12. Burnt Orange + Checkered Skirt + Knee High Boots
If you go apple-picking during the fall, this is another great outfit. Rock this cute burnt orange sweater, with a checkered skirt, and pair it with some cute knee-high boots.
13. Jean Jacket + Black Leggings + Black Hoodie
Wear a cute basic oversized black hoodie with black leggings for fall. To add a little bit of depth to the outfit, wear a jean jacket and pair it with white sneakers.
14. White Sweatshirt + Black Jeans
Keep it casual with a white sweatshirt and black jeans. Add a bit of prep in your step with some ankle boots.
15. Graphic Sweatshirt + Baggy Jeans
Step up your fashion this fall with a cute graphic sweatshirt and some baggie jeans. For shoes, wear some white sneakers and accessorize with a brown handbag.
16. Graphic Shirt + Black jeans
This is a great transitional outfit where it’s not too cold during the day. It’s super casual and cute. Grab a cute graphic tee and pair it with some black jeans and a Converse.
17. All Black Outfit
Earn some fashion points with a monochromatic outfit. Grab a black bodysuit, faux leather leggings, black coatigan, and some black ankle boots. It’s so chic and simple.
18. Faux Leather Shorts + Grey Sweater
I see everyone wearing these faux leather shorts during the fall. This is another great fall outfits. You can grab a grey sweater to go with it and a black handbag.
19. Plaid Shacket + Beige Hoodie + Black Jeans
This is a great layering outfit. The shacket pairs perfectly with the beige hoodie. Grab a pair of black jeans and some Doc Marten boots to go with it.
20. Vibrant Sweater + Dad Jeans + Classic Uggs
If you want to add a little color to your wardrobe for fall, grab a vibrant cropped sweater and pair it with some dad jeans. This fit is so cute for going shopping or making a coffee run in the morning for that boost of energy.
21. Shacket + White Cropped Tee + Jeans
This is a great outfit for all my college girlies. For those days you don’t want to just wear sweatpants and a hoodie.
21. Grey Cardigan + White Tee + Dad Jeans
This outfit is so chic and simple. I’m telling you, it’s all about the basics. Pair a white tee with dad jeans and a long grey cardigan.
22. White Cardigan + White Crop + Ankle Jeans
This is a great everyday fall outfit. You can throw on the cardigan when it starts to get chili. Pair it with a nice fitted white crop top, ankle jeans, and white sneakers.
23. Taupe Blazer + White Tee + Black Jeans
Blazers are so trendy for all seasons. They pair nicely with anything and make the outfit look more “Professional” and chic.
24. Striped Sweater + Faux Leather Leggings
Faux leather leggings are honestly such a must-have for fall. You can pair it with a striped sweater and some boots.
25. Leather Jacket + White Tee + Dad Jeans
This is a great casual date look. Grab a pair of dad jeans and pair it with a white tee and a leather jacket.
26. Cardigan + Sweater Dress
Who doesn’t love a good sweater dress? It’s such a classic staple for fall. You can wear it alone or pair it with a cardigan.
27. California Sweatshirt + Black Sweatpants
Pair a cute California sweatshirt with some sweatpants for a casual day-out look.
28. Dress + Sweater
How PRETTY is this? To get this stylish look, you can pair a white dress with a sweater over it. This is so cozy and cute.
29. Bolero Sweater + Knit Tank + Dad Jeans
Pair a simple knit tank top with a cozy bolero sweater. This is a great transitional outfit.
30. Black Dress + Coatigan
Nothing says “I’m classy” than a cute black dress. You can layer it with a long coatigan ( coat and a cardigan) and some knee-high boots. This also makes for a great date-night outfit.
31. Blazer + Denim Skirt + White Tee
If you’re on the lookout for trendy fall outfits, then this one is perfect. I don’t know if maxi denim skirts have always been popular but lately, I’ve been seeing them everywhere. You can pair the skirt with a basic white tee and to give it more of a chic look, throw on a nice blazer.
32. Sweater + Skirt + Knee High Boots
This is such a chic and elegant outfit. If you’re on the lookout for romantic date night fall outfits, then this is for you.
33. Blazer + Skirt + White Tee + Sweater
Slay this beautiful fall outfit with a blazer, mini skirt, white tee, and a cute little sweater.
34. Nike Shirt + Jeans
This is such a cute outfit. Simply grab a long-sleeved Nike shirt and pair it with some baggy jeans and white sneakers. This is also another great college outfit.
35. Striped Sweater + Trousers
Level up your fall fashion game with trousers. If you want to give your outfit a more chic look, trousers are the way to go.
36. Sweater + Black Pants + Flats
Ok seriously, how cute does this outfit look? Pair some loose-fitted pants with a cute striped sweater and some flats for this effortlessly chic outfit.
37. Blazer + Tank Top + Flare Jeans
Did you ask for business casual fall outfits? If so, pair a white tank top with flare dark blue jeans and top it off with an adorable blazer.
38. Trench Coat + Turtleneck Sweater + Skirt
Okayyy ms fashionista! Give this look a try by pairing a turtleneck sweater and mini skirt with a trench coat.
39. Sherpa Jacket + Hoodie + Jeans
Sherpa jackets are a classic for fall. Everyone wears them. They are so comfy and cute and go with literally anything. You can pair it with a cute hoodie and some jeans with sneakers.<
40. Button Up Shirt + Zip Up Sweater + Straight Leg Jeans
For all my college girlies out there, how cute is this? It’s so casual and simple and so easy to put together. You can get this fit by pairing half zip up sweater and a button up shirt with straight leg pants.
41. White Mock Neck Top + Jeans + Cardigan
Another casual fall outfits for a coffee date. Pair a mock neck top with flare jeans and a cardigan. For the shoes you can either wear Birkenstock clogs ( which are super comfy) or some loafers.
42. Turtleneck Sweater + Jeans
This is a great fall outfit idea for a casual stroll in the park. Pair a cute sweater with ripped jeans and Nike dunks.
43. Wrap Skort + Oversized Sweater + Knee High Boots
This is such a classy and elegant fall date night outfit. Simply grab a cute skort and throw on an oversized sweater with pointed knee-high boots.
44. Knitted Top + Faux Leather Pants
Another great fall outfit inspo with faux leather pants. Pair it with a long-sleeved knit top and ankle booties.
45. Sweater + Faux Leather Shorts
You’re guaranteed to be turning heads left and right with this outfit. To recreate this chic outfit grab a pair of faux leather shorts and throw on a cute sweater with pointed knee-high boots.
46. Coatigan + White Top + Jeans
This is a great romantic date night look. I love how nicely everything pairs. Grab a fitted white tee with a coatigan and jeans.
47. Sleeveless Top + Straight Leg Pants
This is more of a transitional fall outfits. Throw on a mock neck sleeveless top with straight-leg jeans and pointed booties for the perfect fall outfit.
48. Coatigan + Hoodie + Sweatpants
If you’re into more casual fall outfits. This is perfect. Slay this look with a grey hoodie, sweatpants, and coatigan. I think wearing mini classic Uggs would look amazing with this.
49. Turtleneck Bodysuit + Camel Cardigan + Grey Sweatpants
Fall into the crisp breeze of autumn with this look. Throw on some cute sweats, a turtleneck bodysuit, a camel cardigan, and Uggs.
50. Trench Coat + Sweater Dress
This is another one of the best fall outfits. Grab a cute sweater dress and pair it with a trench coat and knee-high boots.
51. Black Cardigan + Faux Leather Pants + Sweater
This is such a classy and elegant outfit idea for fall. You can pair the faux leather pants with a cute sweater and a coatigan.
52. Sherpa Jacket + Black Pants + White Tee
This easy-breezy fall outfits is so cute and simple. All you need is black pants, a white tee, and a Sherpa jacket. For shoes, you can wear Doc Martens or any other type of boots you’d like.
53. White Pants + Black Top + Black Blazer
Rock another great business casual fall outfits. Pair the black blazer with a basic black top and white pants. To finish off the look, grab a pair of mules and accessorize with a black handbag.
This Article Is All About 50 Cute Summer To Fall Transition Outfit Ideas You Will Love!