shoe purgatory

Shoe Purgatory: What It Is and How To Fix It

Shoe purgatory is a topic I feel like I can write about both every fall and every spring. And still, every fall and every spring, like clockwork, I receive questions about it. 

First, let’s start with what exactly is shoe purgatory? Shoe purgatory is that in-between time of year when it’s too cold for sandals and yet, not cold enough for boots.

I know, you’re nodding your head right now, because if you live in Ohio – or anywhere else that has seasonal changes, you’ve encountered this problem too. The cold hard truth is that many shoe wardrobes go straight from sandals to boots (or boots to sandals in the spring) and this in-between time (aka shoe purgatory) is a killer. I was going to say that it is hell – but I’ve used that pun before and felt it was getting stale!

The Shoe Struggle is Real

The other day, I received this message from a person in Cincinnati that’s a member of my private Facebook group, All Dressed Up With SOMEWHERE To Go. Which if you’re not part of, I highly suggest joining ASAP! It’s a private, carefully moderated group where people post fashion questions, ask for opinions, share great finds – and I weigh in with answers too. It’s a great group – everyone is really nice and supportive AND, bonus, it’s kind of a direct line to me, without having to actually hire me, lol!

Ok, anyway, back to the question…

Reader: Will you do a piece on shoe options in this warm weather transition to fall? Especially down in Cincinnati, where it stays hot. I swear, I never know what shoes to wear. It drives me crazy.

Me: You and everyone else that has four seasons. I like to call this time Shoe Purgatory. And thank you for the suggestion – readers’ questions always give me my best ideas. BTW, a post is in the works!!

Reader: Thank you! And it’s worse in Cincinnati because it’s much hotter, so you look like a freak no matter what! I love following you and can’t wait for the post!

So yeah, the shoe purgatory dilemma is real. And you’re not alone in the struggle of not knowing what shoes to wear at this time of year. When there can be a range from 40 – 80 degrees within the week, and sometimes even within a day, it’s rough. And when the calendar says it’s fall, it feels weird to wear sandals. But there is no snow on the ground, so it feels too early to break out the boots!

So What’s The Shoe Purgatory Fix?

The “fix” is for the shoe to be transitional. To feel in-between. That way it can fill the gap from sandal season to boot season.

And how is that done? Well, there are two ways: one is with color and the other with shape/style. Lighter colors feel more transitional or warm weather-ish. Think white or light nudes as opposed to dark green or rust. And, conversely, those darker colors register more wintery.

Then there is the element of the shape or style of the shoes. We’ve already established that sandals feel like summer and boots winter. Sandals are open. Toes are showing. It’s all hanging out (so to speak). And boots are the opposite, everything is covered – toes, vamp, ankles – it’s all hidden away.

The ideal transitional shoe is one that is closed-toe (bye, bye flip-flops) AND still, shows some skin. And what shoes are like that, you ask? 

My shortlist of ideal transitional shoes includes the following: 

  1. Ballet flatlook for a slightly pointed or elongated toe box so that it visually mimics the look of a heel. These work because the toe is covered and the top of the foot (the vamp) is showing skin.
  2.  Mule – kind of like a ballet flat without the back. Again, look for the pointed or elongated toe box. And here the skin that shoes are the heel and ankle. Very chic but not good for rainy days.
  3. Loafer/ Driving Moc – these are a classic and rarely go out of style. I’ve had the same pair for a decade and they’re still going strong. These look especially transitional when paired with ankle-length pants (so some skin shows!)
  4. Sneaker – a cool sneaker can be worn everywhere these days. Depending on the environment, with a suit or a dress too.To achieve a more transitional feel, wear them with no-show socks to again (I sound like a broken record) show skin. 
  5. Heel –  a kitten or block heel will feel a little less dressy than a traditional pump, but all of these styles work as transitional shoes. A heel checks all of the boxes for a bridging-the-gap shoe.

And if you’re a diehard sandal-to-boots person, here are a few boot tricks… 

  1. Ankle bootie – look for one in a lighter color, with cutout detail. The cutout (often found in the ankle region) allows some skin to show while keeping the tootsies covered.
  2. Play with colors –  a more winter silhouette, such as a bootie, in a lighter color like white feels perfectly appropriate and even fresh for transitional weather.

And last but not least, a pro tip – since this transitional season is rather short, you should be sparing in your transitional shoe collection. A few key pairs can help you ride out shoe purgatory in style!

shoe purgatory

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Thank you to District Gallery for a beautiful location for photos!


Cleveland-based personal stylist and fashion blogger.

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