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Clarks Reely Maria Ankle Bootie

This is a well made shoe with tidy stitching and solid hardware. Its minimalistic look and neat ankle fit makes it ideal for skirts and dresses as well as trousers and jeans. Runs true to size, and is very comfortable. A good city walking shoe if you’re good in a two inch heel.

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Franco Sarto ‘Yonkers’ Stretch Boot

This best part about this boot is that it slims at the ankle, making it ideal for midis and dressier occasions. It runs true to size and is available up to size 12, some sizes in narrow and wide widths. It’s stretchy pull on nature makes it work for both a narrow and wider calf. I did find it hard to pull on, but that will loosen up over time. The addition of an insole will soften the footbed.

Currently 20% off.

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Report Judith Ankle Boots

I really liked these desert boots! And they are SO comfortable. They taper quite nicely against the ankle which means they are a no brainer with casual dresses and skirts. They run true to size and are available in several earthy tones. Remember that waterproofing spray will weatherproof these suede darlings perfectly.

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Report Marks Ankle Boot

I found these quite comfortable, especially with an extra cushioning insole. I really liked the shape of the toe, stable heel, and clean design. They require a little effort to pull on, but the leather loosens up in no time. You might need to size up half a size. Spray with waterproofing spray and they’re fab for wet weather.

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B. Makowsky Heist Pump

I almost bought these, which should tell you that they are comfortable! The square toe box is right on-trend and the retro feeling of the shoe is fabulous. I adore the stable heel. I like how the mary jane strap is positioned lower on the foot because it’s less horizontally cutting that way. Size up half a size, and be sure to check out all three colour options.

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Ros Hommerson Bonn Slingback Sandals

The reviews speak the truth. These shoes are very comfortable, although not for a broader foot. They are super soft and squishy and look as good in black as they do colour-blocked. The elastic portion on the strap is ample and genius. They run true to size.

As I write this they are on sale for $77.28.

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