As the colder months roll in, I’ve come to realize how essential it is to have a pair of winter slip-on booties that I can put on quickly while standing. I don’t want to sit on the floor or a bench and fuss with laces and buckles–a challenge for my arthritic fingers. Plus, a cozy pair of pull-on booties that provide enough space for swollen feet, allowing me to move without any painful pressure? Sounds heavenly.

With the right pair of slip-on boots, I can quickly head out for walks with my dog or make those last-minute trips to the store without worrying about discomfort or struggling to get my boots on.

I asked the Barking Dog Shoes Facebook community for their favorite slip-on boots and they came through again!

❄️ The Question

“Who is in this deep freeze we’re having? Do you have any slip-on winter boot recommendations that have some level of arch support?

I love my Merrell Moabs, but don’t want to fuss with laces when taking the dog out. I have a pair of my son’s old Bogs, but they feel like concrete blocks—and my ankle has been giving me fits lately, so I need a bit of flexibility.”

👢 Crowdsourced Answers: Winter Slip-On Boots (and Insoles) People Actually Like

Kizik Slip-Ons (Juno 2 Low, other styles)

• Why people like them: Truly hands-free—just step in and go. Easy for quick dog walks.
• Comfort notes: Warm, flexible, and roomy enough for custom orthotics. Not fully waterproof, but fine for short outings and even light shoveling with wool socks.
• Watch-out: Some users mention socks slipping unless orthotics are inserted.

Orthofeet Hands-Free Boots (Blaire, Bliss)

• Why people like them: Excellent for high arches and high-volume feet.
• Comfort notes: Comes with customizable arch support right in the box, which is a big win for foot pain sufferers.

FitFlop Winter Boots

• Why people like them: Consistently praised for built-in arch support.
• Comfort notes: Warm, supportive, and easy to manage—even with gloves. Slip-on feel, though many styles use a simple front zipper.
• Extra: Several commenters said they’re worth the splurge (especially when found on sale).

Skechers Slip-On Winter Boots

• Why people like them: Affordable, lightweight, and easy to slip on.
• Comfort notes: Multiple commenters called them a “game changer” for everyday winter wear.
• Bonus: Zippered styles available for extra ease.

Chaco Options (Ramble, Pull-On Waterproof Styles)

• Why people like them: Solid support and good traction.
• Comfort notes: Ramble is more of a bootie; pull-on waterproof versions work well if you can find them.
• Extra: Chaco fans love the stability for quick outdoor trips.

Merrell Encore Ice Clogs

• Why people like them: Warm, cozy, and easy to slide on.
• Comfort notes: Familiar Merrell feel without laces—great for icy conditions.

LL Bean Boots (Zip-Up & Insulated Styles)

• Why people like them: Surprisingly supportive thanks to a steel shank.
• Comfort notes: Insulated versions are dramatically warmer than uninsulated ones.
• Trade-off: Zip-up versions are easier but slightly less supportive than lace-ups.

LEMS Waterproof Chelsea Boots

• Why people like them: Minimalist design with waterproof protection.
• Comfort notes: Easy pull-on style that still works well with supportive insoles.

Oofos Londoner Boots

• Why people like them: Known for shock absorption and recovery-level comfort.
• Comfort notes: Warm, soft, and easy on sensitive feet.

Muck Boots, Manitoba Mukluks

• Why people like them: Extreme cold performance.
• Comfort notes: Warmth and insulation were the big wins here, especially in sub-zero windchills.

🦶 Insoles & Safety Add-Ons (Smart Crowd Wisdom)

Swappable Insoles

• Several commenters recommended buying multiple pairs of your favorite orthotics and rotating them across boots—much easier than constantly swapping.

Yaktrax

• Not boots, but highly recommended for icy conditions.
• Flexible, pull-over traction devices that significantly reduce slipping when walking dogs or shoveling.