The Best Shoes to Transition From Summer to Fall

Courtesy of the retailers

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.

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Each product we feature has been independently selected and reviewed by our editorial team. If you make a purchase using the links included, we may earn commission.

1 of 22

Franco Sarto Jolette Loafers

Courtesy of Zappos

These metallic loafers are equal parts funky and classic, and will freshen up any fall outfit.

To buy: zappos.com, $109

2 of 22

Clarks Keesha Luca Loafer

Courtesy of Zappos

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

3 of 22

Off the Beaten Track Metaphor Sandals

Courtesy of Zappos

Side cutouts and an open toe make this boot-sandal hybrid ideal for warmer days and destination this fall.

To buy: zappos.com, $149

4 of 22

Kenneth Cole New York Kam Sneaker

Courtesy of Amazon

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

5 of 22

Louise et Cie Felta Cutout Oxford

Courtesy of Nordstrom

The perforated details and side cutouts take this classic loafer to new modern heights.

To buy: nordstrom.com, $149

6 of 22

Vince Camuto Isaura Slip-on Loafer

Courtesy of Zappos

Nothing can beat the comfort and elegance of a black leather slip-on loafer.

To buy: zappos.com, $100

7 of 22

Rockport Total Motion Audrina Ghillie Booties

Courtesy of Zappos

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

8 of 22

Salvatore Ferragamo Calfskin Loafer

Courtesy of Zappos

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

9 of 22

Anthropologie Bow-tied Slingback Flats

Courtesy of Anthropologie

How cute is this bold suede slingback flat?

To buy: anthropologie.com, $128

10 of 22

Everlane the Suede Heel Mule

Courtesy of Everlane

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

11 of 22

Gucci Brixton Convertible Loafer

Courtesy of Nordstrom

A shoe that does double duty as a loafer and a slipper? What else could a traveler ask for?

To buy: nordstrom.com, $630

12 of 22

UGG Australia Brinley Moccasins

Courtesy of UGG

This leather and suede loafer has contrast stitching and a pretty bow detail.

To buy: ugg.com, $120

13 of 22

Latigo Vivvy Open-toe Leather Booties

Courtesy of Lord & Taylor

This classic open-toe bootie with a stacked heel will dress *up* any casual outfit.

To buy: lordandtaylor.com, $130

14 of 22

Pour la Victoire Selma Mary Jane

Courtesy of Pour La Victoire

This modern take on the classic Mary Jane combines black leather and suede.

To buy: pourlavictoire.com, $245

15 of 22

San Edelman Farrow Ballet Flat

Courtesy of Nordstrom

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)

16 of 22

Fendi Junia Printed Cap-toe Espadrille

Courtesy of Neiman Marcus

The way we see it, espadrilles are always a good idea — even in chillier weather.

To buy: neimanmarcus.com, $300 (originally $500)

17 of 22

Rebecca Minkoff Everly Mule

Courtesy of Nordstrom

This chic, oxford-inspired mule is embellished with barbell studs that add an edgy vibe.

To buy: nordstrom.com, $195

18 of 22

L.K. Bennett Velvet Mary Jane Point Toe Flats

Courtesy of Saks Fifth Avenue

There is something very cozy and warm about velvet, and that makes it perfect for fall.

To buy: saksfifthavenue.com, $295

19 of 22

Vince Cynthia Leather Espadrille Sneakers

Courtesy of Saks Fifth Avenue

Instead of sneakers, opt for espadrille-style kicks that look so vacation-ready.

To buy: saksfifthavenue.com, $110 (originally $275)

20 of 22

Cole Haan Piper Mule

Courtesy of Cole Haan

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

21 of 22

Lucky Brand Rixanne Cutout Bootie

Courtesy of Nordstrom

The side cutouts and peep toe details make this suede bootie the perfect transitional shoe.

To buy: nordstrom.com, $119

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21 Stylish Shoes to Take Your Outfits From Summer to Fall

1 of 22

Franco Sarto Jolette Loafers

2 of 22

Clarks Keesha Luca Loafer

3 of 22

Off the Beaten Track Metaphor Sandals

4 of 22

Kenneth Cole New York Kam Sneaker

5 of 22

Louise et Cie Felta Cutout Oxford

6 of 22

Vince Camuto Isaura Slip-on Loafer

7 of 22

Rockport Total Motion Audrina Ghillie Booties

8 of 22

Salvatore Ferragamo Calfskin Loafer

9 of 22

Anthropologie Bow-tied Slingback Flats

10 of 22

Everlane the Suede Heel Mule

11 of 22

Gucci Brixton Convertible Loafer

12 of 22

UGG Australia Brinley Moccasins

13 of 22

Latigo Vivvy Open-toe Leather Booties

14 of 22

Pour la Victoire Selma Mary Jane

15 of 22

San Edelman Farrow Ballet Flat

16 of 22

Fendi Junia Printed Cap-toe Espadrille

17 of 22

Rebecca Minkoff Everly Mule

18 of 22

L.K. Bennett Velvet Mary Jane Point Toe Flats

19 of 22

Vince Cynthia Leather Espadrille Sneakers

20 of 22

Cole Haan Piper Mule

21 of 22

Lucky Brand Rixanne Cutout Bootie

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