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Paul Green “Ditto” Ankle Boots

This brand is pricey but worth EVERY penny. British footwear designer Paul Green makes beautiful shoes that are comfortable and last for several seasons. This sturdy little slip-on cowboy boot is no exception. Available both in tan and grey, it’s just the type of ankle boot you’re after if you like a bit of heel with your casual look. Refined, yet rugged and very walkable. I want these.

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Miz Mooz “Bonnie” Knee-High Boot

This boot is perfect for the petite lass who has a wider foot and shapely calf. The shaft height is short, the toe box roomy, the instep high and the heel ever so slightly wedged. Cute, casual, comfy and a little bohemian. I vote red for something a little different.

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Miz Mooz “Carlito” Ankle Boots

I almost fainted with excitement when I saw these boots because apple green is my very favourite colour (hence its dominance on this website). Frye makes fabulous cowboy boots, but Miz Mooz makes an even more comfortable version that’s easier to pull on. Size up half a size and wear a thicker sock if necessary. This is the perfect Spring boot if ever there was one.

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Calvin Klein ‘Tipper’ Tall Boot

These boots are extremely comfortable. They will work for gals who have smaller calves, but the multiple bands of back elastic will comfortably stretch up to 14 inches. If you have a high instep and need a roomy toe-box, give these boots a bash. Clean, sleek, casual and versatile.

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Aquatalia “Aurora” Weatherproof Boots

The picture does not do these outstanding little “Chanel-esque” boots justice. They are so, so, so warm and comfortable I could faint. The quilted uppers are like a blanket against your shins! They’re super stylish for all casual days but especially when there is snow, ice, sleet or rain underfoot. You’ll have happy dry feet all Winter long sporting these babies.

Right now they are on sale for $174.65.

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Cutest Little Rain Boot Ever

I have never in my life put a more comfortable ped on my feet. These beautiful little rain boots are like going barefoot. It’s unbelievable. Light weight, cushioning, flexible, soft and absolutely adorable. It looks like you’re wearing a fun Fauvist painting on your feet, which is a huge pick-me-up on a wet, grey day.

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Miz Mooz Short Cowboy Boots

I strongly encourage the look of short cowboy boots under boot cut or straight-leg jeans for casual settings. Perfect for Mums and gals on the go. They look hip when matched with a simple T or knit top and structured blazer. Quite an ageless look. These Miz Mooz boots are so comfortable I could scarcely believe the smiles on my happy feet. And you can fit in plenty of insoles, cozy socks and an orthotic if you need to. The distressed look of the leather adds a vintage feel to your outfit which I think looks cool. No need to worry if they get scuffed or drenched in the rain. Brilliant.

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Comfy Round Toe Bootie

Booties are a great alternative on days when you want to wear socks with your shoes, but don’t want to wear boots, loafers or oxfords. These little darlings are delicious and available in three colours (black, grey and tomato red). The leather is soft and stretchable and the 2 inch heel is perfect. I had to go up half a size to accommodate my long toes and insole but you might be fine in your normal foot size. I have the red and am putting them through their stylish paces right now.

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Stacked Heel Ankle Booties

These trendy high fashion babies are fabulous. They’re not what I’d call 8-hour walking shoes but totally comfortable if you can wear a heel for a few hours at a time. They’re best with skirts and dresses when you add a dark hose or tights thereby giving you your long lean line. Alternatively, wear them over skinnies or cigarette pants. These booties are about showing off the clever design detailing so don’t hide them under boot cuts or slacks.

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