July 19, 2019 4 min read

Hey there, OTBT wanderers!

Enjoying your summer so far? We’re about midway through the season and currently in the midst of a massive heatwave. All these 90°F days have us blasting the AC, lathering up the sunscreen, and doing just about anything we can to keep cool in the intense heat.

And yes, we’re starting to get excited for fall to arrive.

Maybe you’re in the same boat as us. While you love all the beach trips, barbeques, and nighttime summer stargazing, you’re also secretly longing for the crisp, cool air of autumn. Hey, no judgement here. Who doesn’t love the season of pumpkin spice and cozy sweaters?

But we do have a long way to go before we get there. So before boot season is fully upon us, let’s invest in shoe styles that can pull double-duty for both summer and fall styling. We’re talking about transitional footwear, the perfect option to wear in-between seasons.

Which shoes are the best for the seasonal transition? Here’s six summer-to-fall OTBT picks that are now under $99!

Strappy Heeled Platforms

The platform sandal is a classic summer shoe staple for 2019. Chunky heels give off a bold, yet playful vibe that pairs perfectly with all your favorite warm-weather dresses and skirts. When it’s time for fall, strappy heeled platforms can effortlessly transition into the seasonal shift, with just a few simple outfit changes. Swap out the skirts and dresses for jeans and tie it all together with your favorite autumn top.

Styled after the iconic Bushnell platform wedges, the Indio is a strappy heel that’s an excellent summer transition piece. Available in Gold, Copper, Pewter, and Black, these block-heeled sandals are a modern take on asymmetrical styling.

Best of all, you can snag ‘em now for just $68.95.

(Photo Credit: @livekerfully)

Transitional Sandals

When you’re not yet ready to commit to boots, transitional sandals are sure to do the trick. Open-toe designs, cut-outs, and perforated detailing can help strike the perfect balance between summer sandal and fall bootie. Pair them with just about anything – jeggings, shorts, dresses, or skirts. They’re sure to make any outfit look awesome.

The Metaphor is still one of our favorite transitional sandals, with its adjustable ankle strap and memory foam padded sock creating a secure and comfy fit that we just can’t get enough of. This style comes in five trendy colors, including one with gorgeous, grid-cut design, if you’re looking for something with a more artisanal appearance.

Now 40% off, these transitional heels are an absolute essential to make the summer-to-fall transition as easy and effortless as possible.

Cork Wedge Sandals

When it comes to shoes that work flawlessly in both summer and fall, cork wedge sandals are a great pick for in-between seasons. Chick cork bottoms can give off either a beachy warm-weather vibe or rustic, autumnal look, depending on how you choose to style them.

Looking for cork wedges that are as comfy as they are cute? You’re going to want to check out the Elizabeth. These surprisingly lightweight sandals feature a thick wedge with memory foam padding and an adjustable velcro strap for the perfect fit.

Snag these cute and comfortable wedges now for over 25% off their original price. Trust us; you won’t regret it.

Closed-Toe Wedges

Here at OTBT, we’re all about the wedges. It’s what we’re most known for and what we enjoy wearing the most during the spring and summer seasons. But wedges aren’t only just warm-weather shoes. If you’re looking for a comfy pick that you can wear well into the fall season, consider closed-toe wedges.

One of our personal favorites is the Companion, a sporty, mary jane inspired low-platform wedge made for restless wanderers everywhere. Crafted with varnished leather and a contoured cork footbed, these comfy closed-toe wedges cradle your feet with every step, making them the ultimate women’s walking shoe.

Wander on in style with this lovely travel companion, now 36% off.


Like to keep things chill and casual? Slip-on kicks are our top pick for easy and effortless summer-to-fall styling. Pop them on your feet to run errands, walk the dog, go shopping, or meet up with friends. Not only do they look absolutely adorable with shorts and dresses for summer, but they also pair perfectly with your favorite jeans and tee-shirt combo for when the weather gets a bit chillier.

When it comes to chic and comfy slip-ons that are a must-have for the summer and fall season, you can’t go wrong with a pair of the Universe. This sneaker-loafer hybrid is incredibly lightweight and flexible, perfect for tossing into your bag for when you’re headed out on the town and need an extra pair of shoes for walking. The perforated design allows for breathability in the summer heat, while their closed-up design makes them a perfect early fall essential.

And now available for 30% off, the Universe in black is an absolute steal.

(Photo Credit: @amandamcox_)


Nothing makes the summer to fall fashion transition easier than a cute and comfy pair of kicks! White sneakers are an incredibly versatile shoe for all seasons and can be worn with virtually everything, from dresses to leggings and everything in between. If you don’t have a pair in your closet, now’s the time to invest in one!

And what better pair to pick than OTBT’s Transfer sneakers? These sporty, lightweight kicks are unbelievably comfy, with sock-inspired top-line that makes them easy to slip on and go, no lacing required. Their chic athleisure-inspired design is all the rage this season, making them a fun and easy pick for all your weekend adventures.

Now only $88.95, the Transfer is at the lowest price it’s ever been. Snag these comfortable, casual shoes now while supplies last!


So there you have it - our summer-to-fall women's shoe style guide! Which of these shoes would you snag for the seasonal transition? How would you style them? Let us know in the comments down below!

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