September 07, 2018 4 min read

Hey there, OTBT wanderers!

Ready for chilly temps, cozy sweaters, and pumpkin spice lattes? Fall is just around the corner, and we couldn’t be more excited for all of the off the beaten track adventures this new season will bring!

While we may be hyped to don our infinity scarves and ankle boots, and head off on an off the beaten track adventure, the weather sure may not be ready for just a sudden seasonal shift. Scorching 90°F temps and hot, sticky humidity may unfortunately still be the norm well into September or even October, depending on where you live.

What’s an autumn-loving fashionista to do? Well, why not embrace the awkward seasonal transition as a fun fashion challenge? That means picking pieces that pull double-duty as both a late summer staple and early fall favorite. One of the easiest ways to do this is to invest in what we here at OTBT like to call “transition shoes,” footwear that gives you the best of both summer and fall – allowing you to transition seamlessly into the fall fashion scene, even when the weather won’t cooperate.

Want to amp up your transitional wardrobe game, but need some advice to get started? Here’s our top five favorite summer-to-fall transition shoes, along with some OTBT picks that are sure to satisfy your fall fashion craving.

(Photo by Kerry of Live Kerfully)

Heeled Sandals

Summer may be sandal season, but who’s to say September is the cutoff date? Pick the right style and you can wear heeled sandals well into the fall months. Our personal favorite transitional sandal is the Metaphor, with its stylish side cutouts, adjustable ankle strap, and upfront open-toe design to give you just the right amount of coverage for the oncoming fall weather. Despite covering about half the foot, these little stacked-heel sandals provide just enough breathability to keep your feet from sweating in the hot sun. For that perfect fall vibe, stick to dark or warm neutral colors like Medium Brown (pictured), Bronze or Mint, or go for the classic Black. No matter how you wear it, the Metaphor is the ultimate compromise when it comes to balancing summer and fall fashion.

(Photo by Bagshaw Photo and Video)

Closed-Toe Wedge Sandals

Not a heel-loving girl? No problem. You can’t go wrong with a great pair of comfortable closed-toe wedges as a chic and trendy summer-to-fall transition shoe. Wedge sandals like the Elizabeth are an especially great pick if you’re looking for a more rustic or even bohemian-inspired look. What we love about these shoes is their cork-wrapped wedge and memory foam padded sock, which is so insanely comfortable that you’ll never want to take these shoes off. These ultra-comfortable, velcro-strap wedges are incredibly versatile, pairing with everything from distressed denim to flowy maxi-dresses to create a fun and fashionable look. Summer or fall, these trendy sandals are a surefire way to score the most stylish outfit of all.

Leopard Print Flats

When it comes to timeless and fun fashion trends, you can’t go wrong with leopard print. It’s playful, bold, and can be worn virtually all year round! So when picking out the perfect pair of summer-to-fall transition shoes, leopard print is the ideal pattern you’ll want to look out for. The Gamine leopard print flats take complete advantage of that fact. These pony hair leather shoes feature a studded velcro strap to give off a sweet yet edgy mary-jane-inspired vibe. And with its memory foam padding, they’re a style that’s sure to provide that all-day comfort you crave for all of your off the beaten track adventures. So if you’re in need of a fun and trendy new pair of flats for fall, the Gamine may just be the way to go!

Transitional Wedge Sandals

For all you wanderers out there looking for something a bit more sporty, transitional wedge sandals like OTBT’s Waypoint are sure to hit the spot for all your summer-to-fall style needs. Much like the Metaphor, transitional wedges that feature an open toe and stylish cut-outs offer the perfect balance between summer and fall style, making them easy to wear during awkward seasonal transitions. What we love about the Waypoint is its lightweight, sporty bottom, stylish stitching, and soft, perforated finish. This attention to detail makes these shoes an instant favorite in our book – not to mention how insanely comfortable they are for everyday wear. Available in Cacao, Black, and even New Gold, the Waypoint is an absolute winner when it comes to summer-to-fall transitional styling.

Open-Toe Ankle Boots

Ready to make the transition to fall boots, but still want to show off your late summer pedi? Open-toe ankle boots are where it’s at, especially when it comes to the summer-to-fall transition. We like to save these chic booties for when the temperatures are just starting to drop, as they feature just enough coverage to keep you warm when a chilly fall breeze kicks up, yet just enough of a cut-out to let your toes catch the warmth of the mid-afternoon sun. One of our favorite open-toe ankle boots is the Vagabond, with its buttery smooth leather, ankle bracelet embellishment, and three-inch heel. This stylish pick can be dressed down for a casual day with friends or dressed up for a night out on the down. However you wear it, the Vagabond is yet another awesome pick for the upcoming autumn season.

What do you think of our five favorite summer-to-fall transition shoes? Are there any OTBT styles you’re absolutely obsessing over? Let us know in the comments down below!

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