Insomniac Sale Picks: Low-heeled Ankle Boots

*In this late-night feature – which will run Tuesday, Wednesday, and Thursday of each week – I’ll gather up three fun items that are currently on sale online and share them with you! I would LOVE suggestions: Stylish wide-width pumps? Classic v-necked sweaters? Chandelier earrings? Petite dress slacks? What would you like to see featured?*

Lisa requested a few picks for low-heeled, comfortable ankle boots, so here we go:

Aerosoles Play Again ankle boot

Aerosoles Play Again Ankle Boot – was $99, now $39.99

As always, Aerosoles is a great brand for comfort and this sleek little bootie is beautifully designed. With a 2.25″ heel, rounded toe, and double padded memory foam insole, this should be a fantastically walkable pair of shoes. Available in black, brown, gray, and burgundy fabric (faux suede) and black faux leather in US sizes 5 -12. Size availability varies by color.

kork ease maxine

Kork-Ease Maxine – was $295, now $239.99 (and see below)

I’ve been lusting after this pair myself, but haven’t been able to justify them. Kork-Ease is a fantastic brand for comfort and style and this pair of 1 3/4″ heel booties is gorgeous and beloved by customers. The link above leads to Sundance Catalog which has both black and brown in sizes 6 – 8.5, but Nordstrom has brown in 9.5, 6pm has brown in 6 and 6.5, Amazon has black in 6, 7, and 10, and Piperlime has brown in sizes 6-11 at full price. Prices vary by source.


indigo by Clarks Mission Alfa Ankle Boot – was $150, now $89.97 – $149.99

These are the tallest of the low heels, clocking in at 2.75″, but with that rugged platform and Clarks’ legendary knack for designing comfortable footwear, I’m willing to bet these will be fabulously walkable. Plus who could resist that asymmetric zipper?  Available in this taupe-y gray, black, and brown in US sizes 5.5 – 11. Size availability and price vary by color.

Other not-currently-on-sale resources for low-heeled, comfortable ankle boots:

  1. ECCO – You might have noticed that I am wearing my own ECCO boots TO DEATH. I am astonished by how comfy this brand’s shoes are, and have a pair of green pumps waiting in the wings for when spring is finally here. ECCO makes really gorgeous booties, too – like these pared-down beauties – that are bound to be easy on the feet.
  2. Coclico – I’ve taken two pairs of my own Coclicos to the shoe repairman, and been told that they are exquisitely made. They’re also comfortable and utterly gorgeous. This pair of booties is dynamite.
  3. John Fluevog – Not all Fluevogs are created equal, and some will be comfier than others but I can tell you that the Prepare and Operetta families are fantastic. And I’m dying over these.

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details.

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2 Responses to “Insomniac Sale Picks: Low-heeled Ankle Boots”

  1. Keilexandra

    Aerosoles’s Playlist booties from last year, which are the exact same shape as the Play Again booties (but mine are real suede, I would duplicate if they hadn’t changed the material and kept the same price point), remain the most comfortable shoes I’ve ever owned with a 2″+ heel. That comparison includes Clarks and Chie Mihara mid-heels of similar height and (better) quality.

    Tip: I always ask for extra half-insoles when I’m at the Aerosoles store, and they’re happy to give out multiple sets for free with purchase (and sometimes without purchase too).

  2. BamaCarol

    The first time you mentioned how comfortable the ECCO boots were, I took note and ordered some booties. They are THE MOST COMFORTABLE boots I’ve ever worn. And this was the year-of-the-bootie for me. i purchased 6 pair. It is never cold enough to me for regular boots, plus I have knee problems and can’t wear high heels anyway. So booties are the way to go and I wear them with pants and skirts/dresses. I’m keeping a look out for more ECCO booties on sale to add to my growing stash. Thanks for the tips!