I’ve had mixed feelings about tall boots for years. Because I was never truly a skinny-jeans gal, I never rocked the famous “skinnies and tall boots” pairing (or infamous…depending on who you ask). Tall boots with dresses? I just hadn’t found a pair of tall boots that were both stylish AND comfortable enough to wear on repeat.
I decided this was allllll about to change. No, I am NOT going to start promoting skinny jeans….no, no, no. Flares forever and always!
But…after a summer of wearing pretty much ONLY dresses, I decided this was the fall I was going to dedicate some major time to finding a pair of tall boots that met all my requirements — comfort and walkability being at the top of that list.
Spoiler alert: These boots in Cider Spice Leather (more sizes here and here) are my top pick.
Naturalizer’s Tall Boots Are (Yet Again!) My Top Pick For Comfy Fall Shoes
left boots | more sizes | even more sizes | middle boots | more sizes | right boots
Because I wanted a tall boot with a heel and some height, I immediately thought of one of my favorite comfort-shoe brands, Naturalizer. I’ve worn Naturalizer heels for years, and most of its shoes are designed really well for distribution of weight, which is SUPER-important to me with any heeled shoe. Naturalizer boots also have a very comfortable, supportive contoured footbed — cushion and support just where my feet want it — and offer multiple widths in calf fits and footbed sizing.
Second priority: cost. Although I adore the look of Shana’s Loeffler Randalls (check out her review of those boots), I knew I didn’t want to spend that much $ on this type of boot. Naturalizer’s price point? More what I was looking for. Style-wise, I decided to search for boots with either a vintage vibe or a simple clean look that’s not too trendy and would look good with flowy short and longer dresses.
After much debate (in my head only — my husband, as I was online shopping, had absolutely no interest in this debate happening out loud), I ended up with the Kalina, the Genn and the Kyrie, all from Naturalizer.
The Tall Boots I’m Wearing With Dresses This Fall: Pros & Cons
In this video review, I take a look at what I like and don’t like about these three pairs of Naturalizer tall boots, show the boots in action, and also give you an idea of how I’ll be wearing tall boots with dresses this fall.
Keep scrolling for more options in Naturalizer boots and dresses to wear with tall boots as the weather cools down.
Boots featured: Kalina | more sizes | even more sizes | Kyrie | Genn | more Sizes
Outfit details: mini dress (similar) | midi dress (similar) | cardigan-coat
Tall Naturalizer Boots Fit: Wide-Calf & Wide-Width Options
Kalina | more sizes | even more sizes
Kyrie | Genn | more sizes
All three pairs of Naturalizer boots featured fit me true to size. I have a wide-ish foot (but not wide enough I need to wear wide sizing), and the medium-width sizing in all of them fit my foot well. The Kalinas (more sizes here and here) and Kyries both come in medium and wide widths in the footbed.
In terms of calf width, I have thicker calves, and designer boots often don’t fit because of this. All three pairs of the Naturalizer boots, however, fit my calves. The Kalinas come in narrow-, medium- and wide-calf options. They also have hidden elastic on the back that makes them especially comfortable while still looking really nice. The Kyrie boots fit over my thicker calves while still keeping their slouchy vibe, and the Genns were snug but not unbearable. I could have gone up to the wide calf if I wanted more room.
More Tall Naturalizer Boots To Wear With Dresses
More Flowy Mini Dresses To Wear With Tall Boots
More Flowy Midi Dresses To Wear With Tall Boots
Here’s to happy feet, folks! Every season…all year long.
Happy fall, Pinners! Don’t forget to check this out…
Both the Kalina and the Genn look like good options if your legs are on the shorter side.