While we are definitely excited about fall and all the perks that come with it — most notably pumpkin-spiced lattes and beautiful foliage — there is one thing about the season that poses a major fashion challenge. What do you wear for temperatures that can go from the upper 70s to the lower 40s in the span of a single day?
The answer to a cute summer-to-fall outfit is most often layering, and when it comes to matching footwear, designers have come up with some extremely creative ways to combine features appropriate for both seasons into one shoe.
Take slingbacks, for example. They’re closed at the toe and open at the heel. It’s basically the best (and chicest) of both worlds. And don’t let anyone tell you espadrilles are strictly summer-only footwear. Opt for a pair made from genuine leather to keep your feet warm and you’ll never want to wear anything else.
For those of you who like a classic shoe but want something that stands out, consider a comfy loafer or an oxford that has been given a modern update with cutouts or metal details.
Here, we rounded up 21 chic footwear options to take on that tricky in-between weather.
Franco Sarto Jolette Loafers
These metallic loafers are equal parts funky and classic, and will freshen up any fall outfit.
To buy: zappos.com, $109
Clarks Keesha Luca Loafer
While the easy slip-on silhouette of this classic loafer is definitely worthy of your attention, it is the trendy color what sold us on it.
To buy: zappos.com, $70
Off the Beaten Track Metaphor Sandals
Side cutouts and an open toe make this boot-sandal hybrid ideal for warmer days and destination this fall.
To buy: zappos.com, $149
Kenneth Cole New York Kam Sneaker
Cooler and cloudier weather doesn’t mean you can’t wear color. In fact, the bold floral embroidery on these navy sneakers will make your weekend so much brighter and more fun.
To buy: amazon.com, from $62
Louise et Cie Felta Cutout Oxford
The perforated details and side cutouts take this classic loafer to new modern heights.
To buy: nordstrom.com, $149
Vince Camuto Isaura Slip-on Loafer
Nothing can beat the comfort and elegance of a black leather slip-on loafer.
To buy: zappos.com, $100
Rockport Total Motion Audrina Ghillie Booties
These cutout booties are not just sexy, but comfortable, too. They feature truTech technology that provides shock absorption at the heel and guarantees stability.
To buy: zappos.com, $91
Salvatore Ferragamo Calfskin Loafer
If you are looking to invest in a classic and versatile loafer made from quality soft leather, this is it. The gancio buckle on top definitely adds to its allure.
To buy: $550, zappos.com, $550
Anthropologie Bow-tied Slingback Flats
How cute is this bold suede slingback flat?
To buy: anthropologie.com, $128
Everlane the Suede Heel Mule
These sleek, mule-ankle boot hybrids are made of 100 percent Italian suede and have a two-inch heel that adds just the right amount of lift.
To buy: everlane.com, $198
Gucci Brixton Convertible Loafer
A shoe that does double duty as a loafer and a slipper? What else could a traveler ask for?
To buy: nordstrom.com, $630
UGG Australia Brinley Moccasins
This leather and suede loafer has contrast stitching and a pretty bow detail.
To buy: ugg.com, $120
Latigo Vivvy Open-toe Leather Booties
This classic open-toe bootie with a stacked heel will dress *up* any casual outfit.
To buy: lordandtaylor.com, $130
Pour la Victoire Selma Mary Jane
This modern take on the classic Mary Jane combines black leather and suede.
To buy: pourlavictoire.com, $245
San Edelman Farrow Ballet Flat
The pretty floral embroidery on velvet and the metallic heel will make these stand out in a sea of black flats this season.
To buy: nordstrom.com, $60 (originally $100)
Fendi Junia Printed Cap-toe Espadrille
The way we see it, espadrilles are always a good idea — even in chillier weather.
To buy: neimanmarcus.com, $300 (originally $500)
Rebecca Minkoff Everly Mule
This chic, oxford-inspired mule is embellished with barbell studs that add an edgy vibe.
To buy: nordstrom.com, $195
L.K. Bennett Velvet Mary Jane Point Toe Flats
There is something very cozy and warm about velvet, and that makes it perfect for fall.
To buy: saksfifthavenue.com, $295
Vince Cynthia Leather Espadrille Sneakers
Instead of sneakers, opt for espadrille-style kicks that look so vacation-ready.
To buy: saksfifthavenue.com, $110 (originally $275)
Cole Haan Piper Mule
Add a pop of color to an all-black outfit with these pointy-toe mules that offer plenty of cushioning.
To buy: colehaan.com, $140
Lucky Brand Rixanne Cutout Bootie
The side cutouts and peep toe details make this suede bootie the perfect transitional shoe.
To buy: nordstrom.com, $119
