sam edelman ankle bootie

What shoes do you wear when it’s October, 55 degrees and sunny? Sandals? Boots?

Transitional Fall Shoes.

Over and over this question comes up… WHAT SHOES AM I SUPPOSED TO WEAR WHEN the calendar says Fall and IT’S 40, OR 50 OR 60 DEGREES OUTSIDE? Like today? Tomorrow? Last week? Next week? When it’s not sandal weather, but it’s not time to break out the winter boots yet either. TRANSITIONAL FALL SHOES, that’s the answer.

I hear you, the struggle is real! (BTW, the same challenge will happen in March, April and May, so bookmark this page:-) So this week we’re talkin’ transitional footwear and how to fill the shoe gap between sandals and boots.

Right now, September thru November, is what’s affectionately called shoe purgatory, but it doesn’t have to be hell (ha-ha, get what I did there?!?)

How to Fill The Shoe Gap in Your Wardrobe

There are a few shoe styles that fill the shoe gap and easily transition between sandals and boots.

They all have one key thing in common, they show skin, like ankle skin or top of foot skin, BUT generally NOT TOE. And that, there, is precisely what makes them feel “right” when it’s warm-ish but fall-ish too.

So, for those of you with a closet full of sandals and boots, but nothing in-between, this one is for you!  Think, transitional fall shoes. Oh yea, and know, these styles come in at all price points – so I’ve tried to give you at least a few options for each.

Transitional Fall Shoes

Low heel or chunky heel pump

The heel height makes it right for daytime and it does double duty for work or drinks too.

Ankle bootie

The key to this one is making sure you can see some ankle, so either the pants need to be cropped or rolled OR the bootie needs to have a cutout.

Neutral ankle bootie

Same rules apply as the regular ankle bootie, but the neutral color of these make them feel less heavy and more transitional. If you can only get one pair, it might be these. The neutral color goes with everything.


This is the ode to the 90’s but with a modern twist – I love the comfort and ease of a mule, especially a flat one.

Ballet Flat

This style is a classic.

White Bootie

Ok, a white bootie does not necessarily show skin but because the color is typically associated with summer, it really is the king of transition shoes (that you can wear all year long). I wrote a whole blog post about how to wear them a few years ago and updated the links recently. Check it out here. These are some of my favorites from this season.

See, there ARE shoes to wear when it’s too cold or late in the season for sandals but not cold enough for full-fledged boots. Transitional shoes are the solution to shoe purgatory. Note, all these shoes show skin (but the right kind of skin), and that, my friends is the secret to transitional footwear.

Happy fall dressing and sandal to boot bridging too!

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Photo: Molly Nook


Cleveland-based personal stylist and fashion blogger.

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