It's that time of year when we start savoring the final days of summer while simultaneously daydreaming of our new fall wardrobes.
Some of our favorite retailers have already dropped their fall collections, and naturally we're eyeing those key transitional pieces we can wear now and continue to style as temperatures drop.
For example, silk skirts are great transitional pieces, as they work with various tops and sweaters, as well as different shoes. We also love versatile cardigans, blazers (worn as a jacket or for layering!), and tailored shorts in autumnal hues.
Continue below to shop our picks!
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Summer-to-fall outerwear
Everlane The ReNew Quilted Mid-Length Liner

Dynamite One Button Cinched Blazer
- $89.95
- Dynamite
Wear this blazer as a jacket during the summer or layer it with a turtleneck later this year.

Quince Eco-Knit Milano Stitch Oversized Shirt Jacket
- $69.90
- Quince
Shackets are another great transitional styling piece. They're lightweight enough to wear on a chilly summer evening but can also be added with warmer layers for fall.

Dynamite Cropped Zip Up Sweatshirt
- $54.95
- Dynamite
If you're travelling these next couple of months, be sure to pack a sweatshirt (like this one!) for chillier nights.
Abercrombie & Fitch Drapey Cropped Denim Jacket
- $90
- Abercrombie & Fitch
This dark-wash denim jacket is currently on sale for under $80. It's also available in black.
Summer-to-fall dresses

H&M Gathered Dress

Eloquii Puff Sleeve Fitted Dress
- $77.97
- $129.95
- Eloquii
This is a great summer-to-fall occasion dress because you can wear it with strappy red sandals now or with boots later.

Old Navy Fitted Long-Sleeve Rib-Knit Maxi Dress for Women
This knit maxi dress is made from 96% cotton and is fitted throughout the body. Style it from day to night with your favorite accessories.
By Anthropologie V-Neck Tiered Ruffle Dress
- $180
- Anthropologie
This Anthropologie ruffle dress has a pretty floral print that works well in both the summer and fall. It's also a great option for an early-fall bride.
Express Ribbed High Neck Midi Sweater Dress
- $108
- Express
Wear this Express high-neck sweater dress with heels and a blazer for a night out as we transition from summer to fall.
By Anthropologie The Peregrine Midi Dress
- $160
- Anthropologie
When looking for florals for fall, opt for darker color palettes, like those used for this Anthropologie Peregrine dress.

NBD Akia Maxi Dress
- $188
- Revolve
This long-sleeve maxi dress is made from a slinky jersey fabric, making it a great choice for a late summer nighttime event or another occasion this fall.
Summer-to-fall tops

Banana Republic Bliss Silk Shirt
- $90
- $150
- Banana Republic
Style a silk shirt with a tailored Bermuda shorts when it's warm or with wool trousers when it's cold. It's also a great piece to wear day to night.

Gap Eyelet Ruffle Perfect Shirt
- $41.96
- $59.95
- Gap
We love the ruffle detail that comes with this Gap shirt. It will look great styled beneath a jacket or worn on its own with jeans.

Gap Flannel Big Shirt
- $48.97
- $69.95
- Gap
Gap's Flannel Big Shirt comes in 7 different colors of plaid, from brown and tan to green and navy.

Mango Boat neck T-shirt
- $29.99
- Mango
This boat-neck T-shirt can be worn with shorts and skirts as well as with denim, like a cool pair of wide-leg jeans.
Abercrombie & Fitch Ruched Shell Top
- $40
- Abercrombie & Fitch
Style this 46% cotton and 46% modal shell top on its own when it's warm, or layer it with a light jacket in the fall.
Abercrombie & Fitch Soft Matte Seamless Tee Bodysuit
- $50
- Abercrombie & Fitch
A seamless bodysuit like this one is a great layering piece for summer-to-fall dressing.

Good American Button Down 2.0 Shirt
- $139
- Good American
Of course, a good white button-down is a wardrobe staple, no matter the season.
Summer-to-fall sweaters

Banana Republic Sabel Wool-Blend Turtleneck T-Shirt
- $42
- $70
- Banana Republic
Don't be surprised when you see red trending everywhere this season. Try a red turtleneck, like this one, with black denim or trousers and a pair of slingback heels.

Quince Mongolian Cashmere Crewneck Sweater
- $50
- Quince
This 100% Grade-A mongolian cashmere sweater is just $50 from Quince. Style with jeans or a skirt throughout the autumn months.
J.Crew Emilie patch-pocket sweater lady jacket in stripe
- $138
- J.Crew
This popular J.Crew piece comes in an assortment of colors to best suit your capsule wardrobe. Wear it open over a tank or tee while it's warm or style it buttoned and with denim later in the season.
Everlane The Alpaca V-Neck Vest
- $98
- Everlane
Everlane's alpaca vest is perfect for those in-between days when you don't know what to wear. Style it on its own with a pair of trousers while it's still warm or layer a turtleneck underneath come fall.

H&M Long rib-knit cardigan
- $49.99
- H&M
This long, rib-knit cardigan is a great option for transitioning from summer to fall. Pair it with Bermuda shorts and a T-shirt while it's still warm and opt for the matching knit dress as temperatures cool down.

H&M Mohair-blend Top
- $74.99
- H&M
Style this sweater with white shorts or light-wash denim jeans this summer, or with black pants or a leather skirt come fall.
Summer-to-fall bottoms

Old Navy High-Waisted Mini Skirt for Women
Plaid for fall? Obviously. This cute mini-skirt would look great with black boots and a matching sweater.

Old Navy High-Waisted Satin Cargo Jogger Pants for Women
If you missed out on cargo pants for the summer, be sure to try them this fall. These satin pants have a partially elasticized waist and front and back pockets. Plus, you can adjust the cinched hems to wear them tight against your ankle or more loosely for a relaxed vibe.
Everlane The TENCEL Relaxed Chino
- $118
- Everlane
These Everlane chinos are super soft with a relaxed fit. Style them with a tee or a sweater depending on the weather.

Quince 100% Washable Silk Skirt
- $59.90
- Quince
In our opinion, a silk skirt is a wardrobe must. Pair it with a tank in the summer or with an oversized sweater in the fall and winter. Plus, you can wear it with just about any shoe; sneakers, flats, boots and heels all work well.
Madewell Denim Mid-Rise Maxi Skirt in Pineland Wash
- $98
- Madewell
This denim maxi looks great styled with a T-shirt and sandals, but we'd also love it with a slouchy sweater and boots.

Dynamite Faux Leather Midi Skirt
- $59.95
- Dynamite
This faux leather Dynamite skirt comes in both black and beige. Style with a button-down or a warmer long-sleeved knit top.

Spanx Wide Leg Jeans, Raw Indigo
- $168
- Spanx
We love the way Spanx styled these indigo wide-leg jeans with a butterscotch top. The jeans could also be worn with a white or black crop top as summer comes to a close.