As the days grow shorter and the nights grow cooler, staying comfortably styled becomes more and more of a challenge. If you’re looking in your closet and wondering how you’re going to coordinate for the day when the weather could be warm one moment then all-too-breezy the next, we’ve come up with five shoe styles to help you make the transition between seasons. Because we like to start our solutions from the feet up!

 

Timberland Glancy Rouched Peep Toe

Adding darker browns to your look is the perfect place to start incorporating fall style, and the brown Glancy Rouched Peep Toe from Timberland has just the right amount of side-rouching to keep things interesting. The peep toe remains flirtatiously summery when paired with skinny jeans and a loose blouse, but this bootie’s leather upper and textured rubber heel and sole will look amazing paired with opaque tights and your favorite wool skirt in the full swing of fall, too!

 

Sofft Westwood

Cutout-accented and sporting a block heel, the Westwood from Sofft is a great choice for those of us who just can’t get enough details. Coordinate this beautiful bootie with your favorite summer dress and fall cardigan for the perfect transition outfit. And when the weather gets even cooler? Incorporate sweater tights!

 

Spring Step Amora

The peep toe and hand-painted off-white leather of the Amora bootie from Spring Step is still reminiscent of summer, but the fabulous nature-inspired detailing and cutouts are evocative of fall leaves. We love this bootie with a flowy skirt and a blouse under a cute sweater—it’s the perfect look for a fall weekend brunch or a campus meet-and-greet.

 

Report Fable

Keep your transition look low-key yet tailored with the chunky-heeled slide Fable from Report. The microsuede material is perfect for fall, while the silhouette and peep toe is still oh-so-summer. We adore this style with rolled boyfriend jeans or frayed-hem denim for a gorgeous contrast. Slip on a duster cardigan over a basic tee and you’re all set!

 

Musse & Cloud Aineed

Featuring a sleek silhouette with lace detailing, the Aineed from Musse & Cloud is so perfectly versatile for transitional style it hurts. Coordinate this flat sandal with cut-off denim shorts, a fall color palette long-sleeved top, and a luxurious knit cardigan for effortless style. And if you’re still not ready to let go of summer into September? Swap the shorts for skinny jeans for those last few warm days!

Which style above would you try as we head into the next season?

Tell us in the comments!