This post is inspired by something that happened to me a few weeks ago. I had just come home, unzipped my booties and was hanging around in my socks. Shortly following, my mail lady, Rosa, buzzed my door to let me know I had a package. I live on the 3rd floor of a 4-story pre-war walk-up building in Brooklyn so when I went to head downstairs, I realized I didn’t own any easy shoes I could just throw on. I wasn’t in the mood to put boots on again, I didn’t even want to lace up my Allbirds Tree Runners. This all sounds so silly when I say it now, but at that moment, I just wanted something I could slip on and go. In the summer, I have my Birkenstock Gizehs or my Frye Melanies to do that job, but when it gets cold and I am wearing socks, I identified a hole that needed to be filled.

So I took my question to the smartest place I could think of to ask for recommendations, my Facebook Group which is teeming with women who know things. We all may not know everything but collectively we do. Sure enough, within less than an hour, I had more than enough suggestions to consider. I told them in addition to needing these shoes to grab a package in my lobby — because that would be a ridiculously specific need — I explained that I’d like to be able to wear these shoes to take my garbage out to our building’s garbage area, to run a quick errand to the corner store, or for a quick jaunt in the neighborhood. I didn’t want slippers because, unlike people who can get in a car, my shoes actually need traction, I wanted a style that could be worn at home while also being able to stand up to outdoor use.


I have put together five outfits using some of the slip-on shoes for winter recommendations and brands members of my group suggested and have also included more from them at the end of the post. I’ve styled each look with fun socks and selected them from my favorite sock retailer, John’s Crazy Socks. There is no sponsorship behind this decision, I just really support this company that was founded by a father and son team. John Lee Cronin, the son, is a young man with Down Syndrome and has a love of crazy socks. Together, dad and son started the company in 2016 with a mission to spread happiness. Over half of John’s Crazy Socks employees have a differing ability, 5% of their earnings are donated to the Special Olympics and they continually expand their charity partners by offering and creating socks with specific “awareness” themes, such as our Autism Awareness Socks and Down Syndrome Awareness Socks.

Outfit #1- Allbirds Tree Loungers

slip-on shoes winter

At the recommendation of a few Facebook Group Members, I decided to go with the Allbirds Tree Lounger. I already wear the Allbirds Tree Runners and love them and had already had my eye on the Lounger style. I got a pair in a discontinued burgundy color on Poshmark for about 1/2 the retail cost. They’re super comfortable, look good with or without socks, and, being made of wool, keep my feet really toasty.

I styled these Loungers in their grey shade with a pair of straight-leg jeans from J.Crew, a slouchy re-cashmere sweater from Everlane in sunny yellow, and finished the look with a pair of Starry Starry Night socks.

Outfit #2- Dansko Lucie

slip-on shoes winter

The Lucie style clog from Dansko was another style that got rave reviews from group members and I might pick this pair up too. It’s hard to find anything to argue about when it comes to the Dansko brand as they were built for comfort and for people who require orthotics, this clog will actually accommodate, which I didn’t even know was possible for a clog to do. These shoes have arch support, warm wool uppers, and a 3M Scotchgard finish.

For a cold day, I styled these clogs with fleece leggings from Eileen Fisher, a sweatshirt dress from H&M, a plaid scarf from Tasha, a chunky knit pom-pom hat, and a pair of John’s Crazy Socks that any cat owner will love.

Outfit #3

slip-on shoes winter

You know how it goes, you get home, it’s been a long day and, blast, you forgot something and have to run out again, or your kid just called and now you have to go and pick them up. Fuming, you haven’t even changed out of your dress clothes yet but like heck, you’ll put your uncomfortable shoes back on. This is where easy slip-ons, like these highly recommended Birkenstock Boston clogs, that come lined in shearling and unlined, will come in handy.

The style in the outfit is the shearling-lined pair and I styled them with the Everlane pull-on Dream Pants, a v-neck from Cuyana, a tissue print wool cashmere scarf, and a pair of Westie socks from John’s Crazy Socks.

Outfit #4- Flexus Mella

slip-on shoes winter

There comes a point in the winter where you just get booted out. Even though I have a closet full of Aquatalia booties, by the time March rolls around, I’m sort of done with the day-in-day-out sameness. Having alternatives keeps the boredom at bay. Despite coming highly recommended, I didn’t know much about Flexus shoes. I searched a pair that jumped out at me and liked this Mella style that has a collapsable heel, a snow-grip clip, and faux fur lining. It’s a perfect outdoor shoe you can throw on and go.

I styled the Flexus Mella slip-on shoes skinny jeans from Madewell, a red turtleneck from J.Jill, a hooded poncho from Roots, and a hummingbird pair of socks from John’s Crazy Socks.

Outfit #5- Taos Woollery Clog

slip-on shoes winter

You have decided that today is going to be one of those days that you become the human equivalent of a mud puddle. Your plan is to wear your comfiest, who-cares-how-it-fits-or-looks outfit, find a good binge, and put some serious work towards that couch indent. Then you realize you are out of <blank> and have to leave your cocoon. Not wanting to kill the mood, you slip on your winter clogs and get that quick task done. Highly recommended for the loathsome task were these Taos Woollery clogs. They have a shock-absorbing cork midsole, removable, molded and contoured EVA Curves and Pods®, and a roomy round toe.

I styled this look for your slothy day using this Madewell pull-on jumpsuit, a merino base layer tee, and coffee and wine socks from John’s Crazy Socks.

Shop for More Winter Slip-Ons

Still Shopping? Check Out These Additional Styles. My Thanks to the Facebook Group for the help with this post.