Boots worth investing in. Naturalizer Black Riding Boots  | BP Trolley Gray Ankle Boots | Sam Edelman Cognac Riding Boot | Ashlee Proffitt

Finding boots that feel good AND stand up to many wears AND are gorgeous, can definitely be a chore. Especially if you have feet issues (like myself) that result in comfortable, long-lasting shoes being a requirement, not just a desire.

I have pulled together my top 3 favorite boots that have proven to be comfortable for long periods of time and extended walking distances (which is saying a lot for my feet!) AND versatile, meaning they work with lots of different looks (I’ll show you a few below!) AND long-wearing, meaning I have worn them a ton and they still look beautiful.


  1. Black Riding Boot by Naturalizer
  2. Cognac Riding Boot by Sam Edelman
  3. Gray Ankle Boot by BP Trolley

Boots worth investing in. Naturalizer Black Riding Boots | Ashlee Proffitt
Jeans | Tee | Boots

Boots worth investing in. Naturalizer Black Riding Boots | Ashlee ProffittSweater | Blouse | Leggings | Boots

These boots by Naturalizer are the perfect riding boot! I LOVE the height and that tiny gold buckle is perfect! They feel feminine and not too clunky while still looking like a riding boot. And since they are Naturalizer they are of course, so comfortable! They were available in a wide which which was enormous plus for my hard-to-fit feet and making them that much more a favorite in my closet. If you have problems finding comfortable shoes because of bone structure (like me!) I would highly recommend these. And you can see for yourself how beautiful they look and the perfect addition to any outfit. (My personal favorite is with leggings and an oversize chunky knit sweater.)

Boots worth investing in. | Sam Edelman Cognac Riding Boot | Ashlee ProffittSweater | Plaid | Denim | Boots (similar)

I LOVE these boots pictured here that are by Gianni Bini. They are last season and have clearly held up beautifully. They are feminine with their almond toe and gold detailing. I am SO sad they are no longer available. However, these boots are very similar and for the reasons listed above I don’t think you’ll be disappointed in anything by Naturalizer.

Boots worth investing in. Naturalizer Black Riding Boots  | Ashlee ProffittFlannel | Denim | Ankle Boots

You’ve seen these ankle boots featured here a ton (here | here | here) and I am happy to say I still love them and think they are worth the investment. Super comfy and super versatile.


Styling by Megan Michele. Photography by Laura Foote, CIHI Photo. This post was created in partnership with Rewardstyle and Naturalizer. All opinions, as always, are my own.