Transitional summer to fall outfits are the easy, stylish solution when warm afternoons still flirt with crisp evenings. Pinterest searches show these looks are surging in 2025. Effortless layers, thrifted finds, and caffeine-toned neutrals are trending. They photograph beautifully and wear even better. .
According to Pinterest’s 2025 Fall Trend Report, there is a major pivot toward curated, vintage-forward dressing. Thrift drops are making a comeback.
Additionally, preppy revivals and layered, wearable looks are also back. Use these outfit ideas as building blocks. Start with one statement coat. Add one thrifted treasure. Choose one solid shoe. Remix them with what’s already in your closet.
From oversized outerwear to pleated minis and knitted textures, here are 40+ transitional summer-to-fall outfits defining fall (autumn) style this year
Outfit 1. Cozy STREETWEAR: fur Jacket, Logo Trousers & Statement Loafers
Coffee run, but make it couture. A plush shearling jacket pairs effortlessly with monogram trousers. White socks are tucked into logo loafers. A baseball cap creates a casual street style luxe balance. The oversized tote seals it as an everyday statement.
OUTFIT 2. Leather Jacket with Denim Set and Riding Boots
A vintage-inspired brown leather jacket layered over a dark denim shirt-and-shorts combo, finished with tall riding boots. The silk scarf and Fendi monogram bag elevate the Western edge into quiet-luxury territory.
OUTFIT 3. Oversized Shirt with Vest and Plaid Mini Skirt
Classic academia turns playful with lace-trim socks, tall brown boots, and a knit beret. The mix channels European street style while keeping an intellectual, polished edge.
OUTFIT 4. Oversized Sweater with Mini Skirt and Boots
A chunky knit with a mini balances cozy softness instantly. It also provides statement appeal. Tall boots give the look bold autumn energy.
Outfit 5. cool workwear girly: Bomber Jacket, Mini Skirt & Tank Top
Thrifted bombers are trending with Gen Z. Wear them over tank or oversized t-shirts to soften the edgy vibe with feminine ease.
Outfit 6. Preppy Chic: Vest, Pleated Skirt & Loafers
With “preppy chic” searches up 5,000%, the vest–skirt duo is trending. Loafers and high socks give it a sharp collegiate edge.
Outfit 7. Cozy Layers: Camel Coat, Knit Sweater, Plaid Shorts & Loafers
Classic prep gets a cozy upgrade. A cream camel coat tops layered knits and plaid shorts, paired with socks-and-loafers for a polished but relaxed fall vibe. The structured brown bag ties it all together in understated elegance.
Outfit 8. Countryside Chic: Camel Coat, Knit Layers, Plaid Shorts, AND Riding Boots
Equestrian prep gets a fall twist. This mix of coffee-muted earth tones, layered knits, and riding boots nails the autumn aesthetic.
Outfit 9. Street Athleisure: OVERSIZED Blazer, Striped Tee, ADIDAS Shorts, AND Sneakers
Athleisure meets street-tailored cool. A sharp boxy blazer elevates striped basics. It pairs well with retro Adidas shorts. The outfit is styled with sleek sneakers and a bold touch of accessories.
Outfit 10. Parisian Street Style: Grey Sweater, Ruffle Mini Skirt, Knee-High Boots, and Beret
Cozy chic meets Parisian flair. A chunky grey knit balances out a ruffled mini skirt. It’s styled with glossy knee-high boots. A classic beret and oversized tote complete the look for effortless fall elegance.
Outfit 11. Retro Fall Layers: Striped Rugby, Midi Skirt, Sneakers & Baseball Cap
Preppy meets playful in this café-ready look. A burgundy striped rugby top grounds the outfit, paired with a cream midi skirt and matching Adidas sneakers. The yellow shoulder bag adds a pop of brightness, while the cap and socks keep it laid-back and wearable.
Outfit 12. PREPPY Chic: Bomber Jacket, Tailored Shorts & Loafers
Preppy with a Parisian edge. A dark bomber with a crisp collar meets beige tailored shorts, white socks, and leather loafers. The monogram shoulder bag elevates it from school-uniform nostalgia to polished streetwear.
Outfit 13. Preppy Neutral Core: Pleated Skirt, Cropped Jacket, AND Burgundy Tie
School-uniform nostalgia goes streetwear. A pleated khaki mini skirt and cropped jacket are styled with a burgundy tie, cap, and bandana for sharp contrast. Oversized glasses and chunky jewelry turn the prep-school base into a streetwear fall look.
Outfit 14. Slavic Street STYLE: Tweed Blazer, Mini Skirt, AND Fur Hat
Eastern European chic meets modern streetwear. A structured tweed blazer layers effortlessly over a crisp white shirt and belted khaki mini skirt. Suede knee-high boots ground the look, while the fur hat and leather gloves give it that unmistakable Slavic fall edge. The monogram mini bag ties in a touch of luxury.
Outfit 15. Urban Cozy Luxe: Puffer Jacket, Knit Layers, AND Mini Skirt
A brown puffer layers over a knit sweater and crisp white shirt, balanced by a micro white skirt. Chunky socks and Chanel sneakers ground the look in street-luxury. The teddy bear bag steals the spotlight with playful edge.
Outfit 16. Y2K Preppy Streetwear: Cropped Sweater, Pleated Mini Skirt, Cap, and Statements Accessories
Preppy style with a streetwear contrast. A cropped navy sweater layers over a checked shirt, paired with a pleated white mini skirt and a statement belt. White socks and logo loafers nod to classic prep. The baseball cap, gold jewelry, and playful bag charms push it into Y2K street style.
Outfit 17. Urban Prep: Workwear Jacket, Pleated Mini Skirt, AND Timberland Boots
A khaki workwear jacket layers over a brown top and pleated mini skirt for a preppy-meets-streetwear vibe. Slouchy socks with Timberland boots add rugged edge, while a beanie, braids, and slim sunglasses bring urban-cool balance.
Outfit 18. Preppy Old Money: Blazer, Pleated Mini, AND Tie-as-Scarf
An oversized brown blazer tops a crisp white shirt for relaxed polish. A checked tie worn loosely adds playful prep, while a belted pleated mini skirt keeps it sharp. White socks with camel Uggs ground the look in cozy streetwear balance.
Outfit 19. Retro Preppy Parisian: Oversized Blazer with Riding Boots
An olive shirt-dress with a beige tie layers under an oversized cream blazer for relaxed sophistication. A beret and narrow sunglasses add Parisian flair, while tall chestnut boots with green socks give a utilitarian edge. A brown tote completes the tailored-meets-relaxed balance.
Outfit 20. PREPPY WORKWEAR: Leather Jacket, Pleated Skirt WITH Knee-High Boots
A crisp white shirt and black tie meet a beige pleated mini skirt for tailored edge. An oversized leather jacket, sheer tights, and knee-high boots add urban toughness. A structured bag and headband finish with Paris-meets-London polish.
OUTFIT 21. Fall Checkmate: Cropped Blazer WITH Mini Shorts Set
A plaid cropped blazer with matching mini shorts creates a playful fall uniform. This is balanced by a peek of a white button-down. A cinched belt detail completes the look. Knee-high brown boots ground the look, while gold jewelry and an oversized woven tote add street polish.
OUTFIT 22. Tawny Suede Set with Riding Boots
A tawny suede jacket drapes effortlessly over matching micro shorts, cinched by a slim leather belt. The crisp white crop top is sharply minimalistic. Tall leather riding boots provide an equestrian edge.
outfit 23. Striped Knit Shorts with Oversized Graphic Tee
Effortless cool is redefined with striped knit shorts and an oversized graphic tee, slouched just right for that carefree attitude. The earthy tones echo through a soft shoulder bag and chunky resin bangles. Tall leather biker boots ground the look with urban edge. It’s playful, sporty, and perfectly transitional.
OUTFIT 24. Striped Shorts with Oversized Shirt and Boots
A white button-down styled over striped shorts brings late-summer ease. Black boots ground the look with fall edge, while a suede bag and baseball cap add casual balance. Perfect for transitional days when layering isn’t yet needed.
OUTFIT 25. Lace-Trim Shorts with Oversized Shirt and Yellow Shoulder Bag
Crisp white lace-trim shorts with an oversized button-down create relaxed polish. Pearl necklaces add elegance, while a lemon-yellow bag breaks the neutrals. Dark sunglasses and a messy bun finish the effortless summer-to-fall vibe.
OUTFIT 26. Graphic Tee with Sheer Skirt and Tall Boots
Streetwear meets romance with a cropped Budweiser tee layered over a sheer tiered skirt. The rugged buckled boots and baseball cap bring grit to the softness, creating a playful downtown statement.
OUTFIT 27. Neutral Oversized Jacket with Knit Set and Sneakers
Effortless off-duty style: a soft knit set anchored by an oversized jacket and finished with retro sneakers. The baseball cap and structured tote keep the palette refined and street-ready.
OUTFIT 28. Trench Coat with Striped Shirt and White Shorts
A relaxed trench layered over crisp tailoring makes summer whites feel fall-ready. Neutral sneakers and a baseball cap keep the look casual, while the structured bag adds polish.
OUTFIT 29. Trench Coat with Knit Sweater and Tall Boots
The oversized trench adds structure to a cozy gray knit. It pairs with lace-trim shorts. Knee-high boots sharpen the silhouette for a city-ready fall statement.
OUTFIT 30. Oversized Shirt with Adidas Shorts with Loafers
A relaxed striped shirt contrasts with sporty navy Adidas shorts. Glossy loafers and white socks give the look a polished streetwear twist. Sunglasses and a sleek black bag add effortless city cool.
OUTFIT 31. Bralette with Oversized Jacket and Sweatpants
A playful bralette contrasts with relaxed grey sweatpants, while the oversized jacket throws in a bold proportion play. Finished with slipper-style shoes, socks, and a clutch, the look nails elevated loungewear with an off-duty edge.
OUTFIT 32. Light Blue Romper with Navy Accessories
A light blue romper channels effortless Parisian summer chic. It is styled with a navy sweater draped over the shoulders. A baseball cap adds a sporty finish. Minimal jewelry and casual hair keep the look understated yet sharp, perfect for strolling the city.
OUTFIT 33. Pinstripe Blazer with Mini Skirt and Sneakers
Streetwear power-dressing at its peak: an oversized pinstripe blazer and matching mini skirt styled with a cropped white shirt. Paired with chunky sneakers, tall socks, and a baseball cap, the look redefines suiting with an urban, playful twist.
OUTFIT 34. Miu Miu Cropped Sweater with Micro Skirt and Furry Boots
Miu Miu’s cult-favorite silhouette: a camel cropped cable-knit sweater layered over a crisp white shirt with exposed bra detailing. This is paired with the brand’s signature khaki micro mini skirt, a slim belt, and oversized white furry boots. The look captures Miu Miu’s playful balance of preppy and provocative.
OUTFIT 35. Miu Miu Micro Skirt with Bomber Jacket and Riding Boots
Downtown eclectic: a cropped white shirt with beige tie pairs with a khaki Miu Miu micro skirt. An oversized bomber with shearling collar adds contrast. Riding boots with yellow-and-green socks finish the playful street look.
OUTFIT 36. Butter Yellow Pleated Dress with Riding Boots
Soft sunshine tones with a butter-yellow mini dress and pleated skirt, cinched by a brown leather belt. Tall riding boots and cream socks ground the look. A headband, layered necklaces, and a structured brown bag add playful polish — perfect for late summer into fall.
OUTFIT 37. Grey Tee with Pleated Mini Skirt and Ballet Flats
Effortless minimalism is achieved with a cropped grey t-shirt. It is paired with a pleated cream mini skirt. The outfit is cinched by a black belt with a gold buckle. Black ballet flats, a brown shoulder bag, and statement earrings complete the look. Casual yet polished for warm days transitioning into cooler evenings.
OUTFIT 38. Striped Knit Set with Riding Boots and Bucket Hat
Soft ribbed stripes keep the base playful, while a wide leather belt and tall boots bring autumn-ready structure. A denim bucket hat and slouchy bag finish with relaxed ease, making it an effortless summer-to-fall look.
OUTFIT 39. Striped Rugby Top with Pleated Skirt and Red Sneakers
A striped rugby sweater over a pleated mini skirt brings collegiate charm. It is styled with white knee-high socks and red sneakers for a playful pop. A beret and oversized shades add Parisian streetwear flair.
OUTFIT 40. Suede Jacket with Wide-Leg Trousers and Retro Sneakers
An earthy fall mix with a suede jacket over a cream turtleneck, paired with gray wide-leg trousers. Retro sneakers and a slouchy yellow bag add a relaxed, playful finish.
OUTFIT 41. Oversized Shearling Coat with Mini Skirt and Knee-High Boots
Mafia Boss Fall: an oversized teddy shearling coat layered over a crisp white shirt and olive mini skirt. Tall suede boots ground the look. Sharp layers meet plush textures for a street-ready take on cozy power dressing.
OUTFIT 42. Oversized Jacket with Lace Mini Skirt and Over-the-Knee Boots
A cropped brown jacket and baseball cap add a sporty touch. They balance out the softness of a lace mini skirt. Over-the-knee boots add just the right amount of edge.
OUTFIT 43. Striped Polo with Pleated Mini Skirt
Preppy with a playful twist: a cropped striped polo shirt. It’s tucked into a pale blue pleated mini skirt. It’s cinched with a brown belt. Finished with studded pointed-toe flats and a shoulder bag, the look channels early-2000s nostalgia in a fresh fall-ready way.
OUTFIT 44. Leather Jacket & Denim Cutoffs
Effortlessly cool: a black leather jacket is layered over a simple white tank top. It is styled with frayed denim cutoffs and a brown belt. Tall brown boots and a textured shoulder bag tie the look together, blending downtown edge with casual ease.
OUTFIT 45. Headscarf with Monogram Blouse, Mini Skirt and Loafers
A printed headscarf and oversized sunglasses set a chic Parisian mood. The monogram blouse and striped mini skirt pair with burgundy loafers and white socks for a playful retro twist. Bold accessories keep it polished.
OUTFIT 46. Trench Coat with Cropped Sweatshirt and Striped Wide-Leg Pants
A classic beige trench coat drapes over a cropped grey sweatshirt, giving casual balance to loose striped trousers. Black slide sandals add a relaxed edge, while a baseball cap and structured leather tote elevate the streetwear-meets-parisian mood. The bouquet of white roses completes the effortless city-girl aesthetic.
If you enjoyed these 40+ transitional summer to fall outfits for women, please share the article. Save your favorite pins to our curated HIGHMOORE fall mood board for 2025.
Pin the looks you actually love. Remix them with what’s already in your closet: one statement coat, one thrifted treasure, one solid shoe choice.
For the data behind of the 40+ Transitional women’s summer to fall outfit ideas 2025 explore the full Pinterest 2025 Fall Trend Report.
Discover more from HIGHMOORE
Subscribe to get the latest posts sent to your email.