Few people exude timeless style the way Martha Stewart does, so I take notes when she wears a certain item on repeat. Stewart has been pictured in suede gray booties on more than one occasion. First, with pants and an oversized coat to a fashion show at Paris Fashion Week last year, and again earlier this year with a two-piece maxi skirt set at a Lunar New Year Gala. I’m calling it now: Stewart’s gray booties are going to be the ‘It’ shoe this season, so I’m looking to add a few pairs to my collection for fall.
Easy to pair with leggings and a cozy sweater for the office or even a dress and some tights to go out to dinner, gray boots are a nice little twist on the classic black footwear I typically reach for. What’s better? Amazon’s Prime Big Deal Days sale is going on right now, and all of my favorites are on sale from just $29. From ankle booties to knee-high boots and snow-friendly options, I rounded up some of my favorite gray boots that look both cute and comfortable.
Martha Stewart-Inspired Gray Boots
Soda Pilot Chelsea Ankle Boot
Unlike Stewart’s pair, this option has a lug-sole that’s perfect for walking or even hiking through various terrains and weather conditions. The casual style pairs nicely with your favorite jeans and go-to cozy fall sweater, and thanks to a stretchy fit, it easily slips on and off without any buckles or zippers.
Aerosoles Loloa Fashion Boot
I can’t think of an outfit that these ruffled kitten heel boots wouldn’t elevate, but there’s more than what meets the eye. The insole is lined with a high-density foam that’s designed to absorb shock and the outsole is slip-resistant—both are a huge bonus if you, like me, enjoy walking a lot but suffer from clumsy feet.
Dr. Martens Combs Boot
These boots are a staple in my fall and winter wardrobe, and I can guarantee that they will be in yours, too. Despite how lightweight they are, they’re warm and comfortable enough to walk in for long periods of time. I wear them on my hot girl walks, but thanks to their ankle support and durable exterior, they’re also my go-to for hikes and rainy or snowy weather.
Naturalizer Haley Wedge Bootie
I’ve owned this wedge pair for eight years, and even though I don’t typically wear heels, I can easily walk in these for over an hour thanks to their slight lift and memory foam insole. The suede silhouette is an elevated addition to any fall or winter wardrobe, taking a nod from Stewart’s luxe style.
Sperry Saltwater Emboss Wool Boot
Sperry is known for its boat shoes and the Saltwater Emboss Wool Boots are the all-weather version. They have a rubber outsole designed to provide traction in both wet and dry conditions, along with a cozy microfleece lining. Made of 100 percent leather, these are a great find—especially now that they’re 54 percent off.
Dr. Scholl’s Create Bootie
You know Dr. Scholl’s for its comfortable shoes, and if you don’t, I’m here to tell you from years of experience that you’re missing out; my mom and I have been loyal fans of the brand since I was a kid. Made with a microfiber upper, the fabric is designed to hug your feet in the same way as your favorite cozy sweater. Like many of the brand’s shoes, this pair is made with a flexible insole that absorbs shock while reducing foot pressure and fatigue. TL;DR: More comfort equals more time on the dance floor at holiday parties.
Bacia Sock Ankle Boot
While Stewart favors suede boots, I couldn’t help but gravitate toward these versatile shoes. The soft and breathable knit fabric is a great transitional shoe as we head into fall, and the classic sock style is timeless, so you’ll own these for many years.
Sorel Out N About Wedge Boot
I could see Stewart pulling out these boots for a cozy bonfire party. Pair them with leggings and an oversized sweater or a mini skirt and blazer; either way, you’ll appreciate their flexible insole that’s designed to mold to your foot’s shape over time, along with a waterproof suede exterior.
Dream Pairs Wedge Sneaker Ankle Bootie
Think of these as your favorite sneakers’s older sister, but with a bit more height. These booties can be worn year-round thanks to a low ankle that pairs just as well with a breezy dress as it does with denim and a parka. Wear them with socks while it’s chilly out, then ditch the socks when temps rise again. They’re sturdy, too, with an outsole that’s specifically designed to provide grip and stability.
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