Insomniac Sale Picks: Mid-heeled Ankle Boots

*In this late-night feature – which will run on Tuesday 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?*

Courtney requested a few picks for mid-heeled ankle boots, so here we go:


platform ankle boots

Easy Spirit Parilynn – was $139, now $42.09

Kudos to Easy Spirit for stepping up their style game! This pair is quite similar to a Paul Green pair I own and adore, but at a fraction of the price. The heel is 2.75″ but with a 0.5″ platform, it’ll feel like only 2.25″. Available in this black leather as well as brown leather or taupe suede in U.S. sizes 6 -10, including some D widths. Size availability varies by color. (Also available on Amazon.)

asymmetric zip ankle boots

Steve Madden Jaydun – was $149.95, now $59.99 – $134.99

I love an asymmetric zipper on an ankle boot. This Steve Madden design also boasts a classic almond toe and minimalist styling. It’ll go with everything. Seriously. Heel is 2.5″. Available in this cognac leather as well as black or taupe nubuck in U.S. sizes 5 -10. Size availability varies by color. This similar style also comes in C widths.

grey ankle boot

Easy Street Carson – was $55, now $16.99 – $50.95

This vegan-friendly pair is a fabulous find, since it’s tough enough to work with jeans and a graphic tee but simple enough to pair with a dress and tights for the office, too. With a 2″ heel and a 0.5″ platform, you’ll feel like you’re wearing 1.5″ heels when you slip these on! Available in this gray faux leather as well as brown or black in U.S. sizes 5 – 12, including 2A, C/D, and E widths. Size availability varies by color.

leopard print ankle boots

Naturalizer Harding – was $179, now $71.60

Looking for something a little sassier than basic brown or black? Look no further. These two-tone, black-leopard boots are still neutral enough to be versatile, but will most definitely turn heads. Available in U.S. sizes 5 – 11, including some AA, C, and E widths.

Sustainable resources for mid-heeled ankle boots:

  1. ECCO – Your best bet for sustainability and comfort. The Sculptured line is particularly fab.
  2. Coclico – Exquisite boots handmade in Spain. Love this pared-down black leather pair. If the prices make you gasp, check eBay.
  3. Bali Elf – Gorgeous, handmade ankle boots and oxfords. This tan pair is calling to me …

Other not-currently-on-sale resources for mid-heeled ankle boots:

  1. Clarks – My go-to for comfort and style. This zipper-free ankle boot is on my wishlist.
  2. Frye – If you’re willing to spend a bit more, Fryes will last you FOREVER. The Tabitha is my current fave.
  3. Born – Slightly more rugged, but well-made and super comfy styles.

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details. Sustainable options are either used, handmade, made in the U.S., artisan made in non-sweatshop conditions, or made using sustainable/fair trade practices.

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5 Responses to “Insomniac Sale Picks: Mid-heeled Ankle Boots”

  1. Shanna Mann

    I love the range of widths on Easy Street. Are they a comfort brand like Clarks, do you know?

    • Sally McGraw

      Yes! I thought they might be owned by another company, but looks like they’ve been making comfort shoes under their own name for 50 years. A few are even made in Italy!