Summer is almost over, and it’s the time of year when the warm weather starts move out and the air begins to cool down. We’re not quite there yet, but it is time to start thinking about getting your wardrobe ready for fall. Wearing transition outfits can help you ease into the new season of fall fashion without worrying about the unpredictable weather. Investing in easy layers, breathable fabrics, denim, and lightweight jackets is a great idea. So today, I’m sharing a roundup of summer-to-fall transition outfits that you can wear between summer fashion and fall styling.
50 Summer to Fall Transition Outfits
Today, I’m rounding up 50 outfits to inspire your fall fashion transitional wardrobe. Hopefully this will give you several outfit ideas with extra layers to transition from summer to fall in confidence. Also, feel free to share on your Pinterest board for your fall-winter fashion inspiration.
chic Paperbag Shorts Outfits
Paperbag shorts are the perfect blend of comfort and style, making them so ideal for transitioning from summer to fall. Opt for a chic pair in a tan or neutral tone to keep your outfit feeling seasonal and elevated. Then, style them with a lightweight button-down and sandals for warmer days, or throw on a neutral sweater and a ball cap for a sporty, cozy vibe. Also, for a more polished look, add a blazer for work or layer with a bomber or utility jacket when the temperatures start to dip. These versatile shorts are an overall staple for effortless end of summer outfits. Also, be sure to check out my post on Paper Bag shorts here for more outfit inspo.
White Skirt + lightweight layers Outfits
A chic, high quality white skirt is a summer staple that transitions so beautifully into fall. It’s the kind of piece that feels fresh and timeless, especially when styled with lightweight layers. Pair it with a utility jacket, suede jacket, or a classic bomber for that effortless in between season vibe. You can also keep it simple with a blue button down for a more minimal look. Whether you’re heading out in sneakers for a casual day or dressing it up with heels and a blazer for work, this outfit combo is endlessly versatile.
Cropped Trench Coat Outfits
A cropped trench coat is an overall must have for the summer to fall transition. It’s not only practical but also so on trend right now. This piece instantly elevates any look and works just as well dressed up as it does dressed down. For example, style it with a white skirt and flats for a polished outfit that’s perfect for brunch or the office, or go casual with jeans and sneakers for an easy day out. It’s one of those staples that pulls your whole outfit together so effortlessly.
Striped Sweater + White Jeans Outfits
White jeans are a summer favorite, but they also transition beautifully into fall with the right layers. One of the easiest ways to style them is with a lightweight striped sweater. For example, think classic navy and white or black and white for that effortlessly chic vibe. Dress the look up with ballet flats or sandals, or keep it casual with sneakers. Then, add your favorite neutral bag to tie everything together for a look that’s perfect for weekend plans, errands, or even a casual office day.
Cream Blazer + Jeans Outfits
A cream blazer paired with jeans is the ultimate outfit formula for those in between days when you’re not sure what to wear. It’s polished, easy, and so perfect for a business casual setting. For a chic office-ready look, layer a cream blazer over a classic blue button down and finish with white heels and a matching bag. This combo strikes the perfect balance between professional and effortless. So ideal for the transitional season.
Linen Pants + Neutral T-Shirts Outfits
Linen pants are a summer favorite, but they’re also perfect for transitioning into fall thanks to their lightweight and breathable feel. Choose a pair in a neutral shade like tan, white, or black, and style them with your favorite t-shirt for an easy, chic look. Then, finish the outfit with sneakers or sandals and a classic tote bag. It’s a simple go to that feels laid back but still put together for everyday wear.
Earth Tone Dress Outfits
Dresses are the perfect piece for that in between summer and fall weather. So breezy, comfortable, and easy to style. To start leaning into fall, opt for earth tone colors like chocolate brown or burnt orange. These shades give off that cozy autumn vibe while still working for warmer temps. Then, dress it up with heels and a blazer for the office, or keep it casual with flats and a lightweight sweater tossed over your shoulders for a day out.
Short Sleeve Knit Top + Jeans Outfit
This knit brown top is perfect to wear in summer with linen shorts. It’s also an essential top for transitioning into fall. Here I paired it with skinny Levi blue jeans, nude heels, and a matching brown handbag to creates the perfect pre-fall look for this time of year.
Lightweight Blazer + Jeans Outfit
This white blazer and bamboo handbag are two summer fashion essentials. When transitioning to fall, pair your white blazer with denim jeans, white golden gooses, and a mock neck knit top. This outfit is also the perfect look for a casual date night, brunch with the girls, and more.
Leather Mini Skirt + Short Sleeves Top Outfit
This brown leather mini skirt is the perfect piece to help you transition from summer to fall. For example, wear it with a black halter top, black heels, and a black leather knit handbag for a cocktail party. Another styling option is with a white puff-sleeved blouse, brown heels, and a bamboo statement handbag for work or dinner.
Jean Jacket Over Summer Dresses Outfit Ideas
A piece you need in your wardrobe for transitioning from fall to summer is a simple denim jacket is perfect for this time of year. This light-washed, denim jacket goes perfect over white summer dresses, making them ready to wear for those cooler evenings.
Long Sleeves + Blazer + Short Outfit Ideas
These shorts were ideal for my fashion summer style, and they’re also a great piece to add to your pre-fall wardrobe! Pair them with a puff-sleeve lace white blouse or a matching blazer for a more sophisticated look. Also, check out my post to see how to wear jackets with shorts and all my favorite matching sets here.
White Long Sleeves + Faux Leather Shorts Outfit
This long-sleeved white poplin top is perfect to pair with black faux leather shorts. You can keep it casual with a white sneakers or add a heel black or nude heel for date night. So chic!
Trousers + Lightweight Sweater Outfit
We are seeing wide-leg trousers as one of the biggest fall fashion trends. These cropped white wide-leg pants are the perfect fall transitioning piece because they are lightweight for warmer weather, but still provide some warmth if the nights get cold. Wear them with nude or white kitten heels, a gray knit mid-sleeve top, gold hoop earrings, and a matching nude handbag. We are seeing wide-leg trousers as overall one of the biggest fall fashion trends.
Trench Coat Over Summer Dresses Outfit Idea
A nude buttoned trench coat is an essential item in my transitional outfit formula. It’s so perfect for those pre-fall nights where it starts to get chilly. Wear it over a white lace summer dress for the perfect day to night outfit.
Summer Dresses with Knee Hight Boots Outfit Ideas
Knee-high boots are excellent for pre-fall styling. Pair them with a floral, white, or nude summer dress to add a bit of warmth and to dress up your outfit when you transition from summer to fall. Then, add a shoulder bag, hoop earrings, or a lightweight blazer. These looks are ready for anything from shopping to a night out with friends.
Leather Blazer Over Summer Clothes
Similar to the essential pre-fall jean jacket, a leather blazer is the perfect transitioning piece from summer to fall. Try a tan leather blazer paired with a white maxi summer dress. Then, pair it with a tan handbag and a short, strappy heel to keep a little bit of summer warmth in your outfit. Also, wear a leather blazer over any summer dress for a perfect date night look.
Long Sleeve Blouse + Mini Lace Skirt
Sleeve Blouses are great for pre-fall styling because you can pair them with your summer skirts, shorts, and pants. Pair your white, romantic long-sleeve blouse with your favorite ruffle summer skirt and a pair of sneakers for a perfect casual, but elevated look.
Lightweight Sweaters Over Summer Dresses Outfit Ideas
Not yet ready to stop wearing your favorite summer dress? Simply add a lightweight sweater over your summer clothes when the weather starts to get a bit cooler and it’s one you will continue to wear in the fall-winter season. Try pairing a white sleeveless sweater with your tan summer maxi dress, simple white sneakers, and a tan shoulder bag for an effortlessly chic look. Or also pair your white mini summer dress with a long-sleeved white knit sweater, white golden goose sneakers, and a nude hat for a more casual daily look.
Fall Color Fashion Trends in Short Sleeves T-shirts
Adding fall color fashion trends into your fall fashion wardrobe through your short-sleeved t-shirts is the perfect way to transition into your summer outfits to fall style. A simple lightweight olive green pocket t-shirt is perfectly paired with skinny blue jeans and brown summer sandals, and a matching brown handbag is a perfect look for running errands or hanging out with the girls. Then, add a gold chain belt to accentuate and elevate your look.
Lightweight Trench Coat + Jeans Outfit Idea
A lightweight trench coat is a great transition to a fall jacket when you’re not yet ready to break out your parka or puffer coat. Pair a lightweight trench coat with gray skinny jeans, and a simple white tee, and accessorize with a large black statement handbag, black sunglasses, fun hoop earrings, and gray heels to match.
Leather Blazer + Shorts Outfit Ideas
Not yet ready to hang up your floral summer shorts for the year? Try pairing them with your summer clothes. A matching leather blazer when you transition to fall. Wear your black floral linen shorts with a black turtle neck knit tank, a leather blazer, a black mini handbag with a pop of gold, and black statement heels. Or style your floral blue and orange shorts with nude sandals, a nude leather blazer, statement sunglasses, and an adorable brown mini handbag.
Moto Jacket over White Mini Dress
Nothing says fall like a moto or even a chic utility jacket, but adding it over your favorite white mini dress takes your summer outfits to a chic fashion fashion look! Pair your black moto jacket with your white ruffle mini dress, black leather heeled ankle boots, and a black handbag, with your favorite black statement sunglasses for an effortlessly cool look. This is one of the best key pieces you can own for fall.
White Dress + Fall Accessories
Fall accessories are a perfect way to ease your style into a fall vibe. Style your Love Shack Fancy white mini dress from summer with a brown accent belt, a matching brown leather jacket, and some pearl statement hoop earrings for a perfect early fall date night look.
Knit Dress with Ankle Boots
Knit dresses are a great summer-to-fall outfit transition piece. Pair a white midi sleeveless knit dress with tan, heeled ankle boots, and a tan leather handbag for a chic pre-fall look. The knit dress will keep you warm on those chilly pre-fall evenings but will keep you cool during the day.
White Summer Blouse + Jeans + Brown Boots Outfit Idea
A white, summer, romantic mid-sleeve blouse paired with blue bootcut jeans, and brown heeled boots is a great go-to look for those pre-fall date nights or dinners with the girls. Pair your outfit with fall accessories such as a brown shoulder bag, and chic sunglasses to complete the look.
Key Pieces to Transition into Fall
1. Denim Jacket
2. Trench Coat
3. Lightweight Sweater or Cardigan
4. Knit Tanks
5. Knit Dresses
6. Short Sleeve Tops
7. Long Sleeve Blouses
8. Leather Jacket
9. Blazer
10. Long Sleeve Dresses
11. Utility Jackets
I hope this post gives you some inspiration when choosing your summer-to-fall outfits! Thank you for stopping by!
Shop My Essential Summer to Fall Transitional Pieces
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Please feel free to email me at thegraydetails@gmail.com if you have any questions! I’m always happy to help with styling or picking out a specific outfit for an event! Have an amazing day!!
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