Over and over this question comes up… WHAT SHOES AM I SUPPOSED TO WEAR WHEN 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 boots yet either. I hear you people, 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?!?)

There are 11 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 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’s for you! 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 (just click the pink link and you’ll go right to the retailer, easy, right?)

The Looks and The Shoes

  1. Low heel or chunky heel pump

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

Pump (obsessed with thesethey’re the splurge! Here’s the steal)


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2. 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.

Bootie (similar splurge and similar and similar steal)


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3. Mule

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.

Mule (similar and similar SPLURGE)


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4. Lace up ballet flat

Flat (actual shoe and similar splurge and similar steal)


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5. Smoking Slipper/Loafer

This is a classic style that will never go out of style – I’ve had the same pair for 7 years and they’re as current today as when I bought them.

Loafer (similar and similar lux steal, only 1 size available!)


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6. Classic Ballet Flat

This toe box is more rounded but the scallops keep it interesting.

Ballet Flat (actual shoe and similar and similar steal)


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7. Oxford

The oxford is having a moment, there are sooo many good ones to choose from. I personally like the ones with a creeper bottom like these or these, but OP’s look pretty dang cool too.

Oxford (similar splurge, love em tho and similar MAJOR steal)


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8. Lace up sneakers

We’ve talked before about the essential-ness of sneakers and how to wear them and not look like you’re going to the gym, so they really are a perfect transitional shoe, especially if “done right”.

Sneaker (similar and similar steal)


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9. Slip on Sneaker

The slip on sneaker, is a kissing cousin to the lace up sneaker, it’s a little sleeker but still needs ankle to be shown to make it feel transitional.

Slip-on (similar splurge and similar and similar steal)


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10. Neutral ankle bootie

Same rules apply as the regular ankle bootie (#2) but the neutral color of these make them feel less heavy and more transitional. If you can only get one pair, I’d start with black, but if you’re building your wardrobe this is a great one to add.

Neutral ankle bootie (similar splurge and similar and similar steal)


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11. Mary Janes

Not your school girl Mary Janes, these are all grown up with extra bells and whistles that make them cool not cute.

Mary Janes (similar splurge and similar steal)


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See, there ARE shoes to wear when it’s too cold for sandals but not cold enough for boots. And, the key is, all these shoes show skin (but the right kind of skin), and that, my friends is the secret to transitional footwear. Hope this was useful to get you guys out of shoe purgatory!

Happy fall dressing and sandal to boot bridging!

Taking the Stress out of getting dressed – #TheWardrobeConsultant



In the spirit of full disclosure, I sometimes use affiliate links, which means that when you click links and purchase items, in some, but not all cases, I may receive a nominal (meaning pennies NOT dollars) referral commission. You will NEVER pay more when buying a product through my link.
Plus, when you order through my links (or even just click on them), it helps me see what you all are interested in and therefore be more mindful of you, my readers, when thinking about what to highlight in future blog posts.  Thank you in advance for your support!



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Cleveland-based personal stylist and fashion blogger.

1 Comment

  1. Gloria Abrams Reply

    It is always hard to find the right shoes for this time of the year. Thanks so much for the great ideas.

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