By Meghan Cass
As much as I love welcoming boots and ballet flats back into my wardrobe every fall, one of the hardest things to do is say goodbye to summer sandals.
Comfortista believes that the old rules about post-Labor Day dressing don’t apply to today’s woman. (Winter white is wonderful!) But when it comes to transitional fall footwear, here are a few easy and comfortable guidelines to keep in mind:
Pair bare legs with moderate-coverage sandals
As long as the weather and occasion permits, bare legs continue to be ok in our book! But stay season-appropriate with sandal styles that don’t expose your toes completely.

Example: Peep toes and cutout sandals are the way to go here. The perforated upper on Aerosoles’ Fax Bracket sandals perfectly hits the mark. Sofft’s Reiko sandalfeatures a cage-style design that conveys fall convincingly. For work or more dressy occasions, Sofft’s Pavia sandaland Naturalizer’s Kiril T-strap sandal give you the formality of a pump with subtle sandal attributes.
Hold on to sandals in autumnal colors and materials
Comb your closet for sandals that say September. Think wooden heels, animal skin looks, hardware, suede and leather. Save the pastel uppers as well as cork and espadrille soles for spring.

Example: SoftSpots’ Clover Sandals have a strappy leather upper and faux-wooden wedge that would look great with bootcut jeans and an plush cashmere sweater. And picture FitFlop’s Lolla Slide with wide leg trousers, a fitted top and lightweight leather jacket to complement the shoe’s earthy vibe.
Add tights or leggings to extend sandal season.
In the past, sandals with stockings was considered a fashion faux-pas, but if matched correctly its a great way to get more from your summer shoe selection! The key is choosing a sandal that’s substantial enough to stand up to the hosiery. So pass on delicate or flat styles in favorite of architectural sandals with heels.

Example: Clog-inspired looks like Dansko’s Sara sandalsand Clarks Elements’ Harwich Sailor wedges work brilliantly with a pair of opaque tights.
How do you style your sandals in September and beyond? Share your season-extending strategies below.
Related articles
- What Makes a Sandal “FootSmart”? (blog.footsmart.com)
- Comfortable Sandals for Wide Feet (blog.footsmart.com)





