Which summer staples can I wear into fall?

As August comes to a close and the weather slowly starts to change, it can be more and more challenging to know how to dress stylishly. Luckily, we’re not alone—there’s plenty of help in this area, especially when you have celebrity stylists Emily Current and Meritt Elliott in your corner.
Scroll down for five items you can easily transition from summer to fall, plus pieces to shop now!
Wear these strappy staples with a maxi dress and blazer!
On Damsel in Dior: J. Crew Studded Lace-Up Gladiator Sandals ($158)
MIA Czar Sandal ($170)
Dolce Vita Santa Monica Lace Up Sandal ($129)
The Reformation Dragon Dress ($258)
Pair these cool-girl staples with a skinny or flared jean, a tailored jacket, and perhaps a biker jacket to toughen it up!
THML Clothing Cream Embroidered Top ($79)
Isabel Marant Ethan Embroidered Blouse ($455)
Chloe Oliver The Sonora Peasant Blouse ($99)
Free People Classic Suede Biker Jacket ($420)
Mother Looker Cropped Skinny Jeans ($196)
Wear this ladylike piece with a tucked-in, long-sleeved tee and classic pumps.
Nina Ricci Long Sleeve Top ($1,190)
For Love & Lemons Holly Skirt ($193)
Diane von Furstenberg Bethany Pumps ($325)
Pair a slinky dress with an oversized chunky cardigan and cropped boots.
T by Alexander Wang Stretch Silk Georgette Slip Dress ($550)
The Reformation Eve Dress ($198)
Related: What Should I Wear to a Casual Wedding?
Pair with a black cashmere sweater and ankle booties for casual elegance.
Michael Kors Featherweight Cashmere Sweater ($595)
J Brand White Skinny Jeans ($184)
Forever 21 Pointed Faux Leather Booties ($35)
Report Taft Signature Booties ($130)
Related: What Are Three Easy Ways to Wear a Jumpsuit?

Hailing from the heart of the South and cutting her teeth on the mean streets of New York, Meghan has six years of experience covering fashion, style, celebrities, culture, and human behavior. A longtime devotee of rap music, tacos, and generally perfect weather, she is excited to put down roots in Los Angeles. Her top three style staples are a good pair of cutoff shorts, virtually any kind of colorful digi-print, and a solid set of shades.
-
Dresses Aren't Only for Summer—These 35 J.Crew, Reformation, and Anthro Fall Styles Prove Just That
The best fall dress arrivals.
-
It's the Last Chance to Shop Reformation's Sale—Up to 70% Off
It's selling out fast.
-
Pendant Necklaces, Desert Hues, and Pajama Sets—Michael Kors Ushers In Earthy Elegance for Spring 2026
Fringe, suits, and wallet necklaces were all standouts.
-
Reformation Just Launched Jewelry—Here's What I'm Betting Will Sell Out First
Take my word for it.
-
Sure, Trousers Are a Fall Staple, But IMO, Dresses Are So Much Better—33 Gorgeous Styles From Mango, Reformation, and Anthropologie
An underrated essential.
-
7 Things I Want From Reformation After Seeing These French It-Girl Outfits
If I can't be in Paris this fall, I can at least dress like I am.
-
I Live in Murray Hill—Here Are the 8 Places I Like to Shop for a Fashionable Fall Closet
Stylish sweaters and suedes ahead.
-
These Are the Only Labor Day Weekend Sales That Matter—Shop the Best Deals Thanks to Nordstrom, Madewell, J.Crew, and More
Save big on fall staples.