Back-to-school shopping is in your rearview mirror, but the change of season may have you second guessing your own wardrobe, especially your shoe closet. Those sleek sandals and flimsy flats are no longer cutting it. It’s time for real shoes. But battling subway staircases with strollers and backpacks doesn’t have to mean looking frumpish. Here are 11 comfortable fall-winter shoes, (most of them less than $100!), that are anything but uncool (because you’re not a “regular mom,” you’re a “cool mom”)!Interested in stories like this? Sign up for our eNewsletter New York Family Weekly Scoop
The "Won't Break A Sweat" Shoe
The KEDS Studio Leap ($64.95, Keds.com) feels more like a sleek but sturdy sock than a big and bulky shoe. These lightweight, breathable slip-ons are made with a flexible jersey upper and fixed elastic lacing for on-the-go lifestyles (read: chasing your tot around Central Park). And your feet won't sweat or chafe no matter how many city blocks you traverse thanks to removable footbeds ventilated with foam outsoles and a Dri-Freeze lining moisture control. Throw these on with your workout gear or dress them up with skinny jeans and a printed blouse. Opt for basic black because they'll never reveal their wear and tear – just like you, mama.
The "Weekend Warrior" Shoe
If you're looking for a low-commitment high top that'll take you from pushing a stroller at the farmers market to getting coffee with a co-worker, the SeaVees Maslon Desert Boots ($108, Orvis.com) are a good bet. The simple two-eyelet lace-up design is both cool and casual while suede steps up the style. Flannel lining and a bamboo-jersey footbed, plus a lightweight vulcanized bottom, score major points with moms when it comes to comfort. And these look good with just about anything, from cuffed boyfriend jeans to a t-shirt dress and jean jacket.
The "Date Night" Shoe
Before kids, you may have worn 4-inch heels any time you went below 14th Street. After kids, you can't bear the thought of such sartorial suffering. If you still want to feel "dressed up" without sacrificing your sanity consider a stacked heel like the Soft Comfort Heartbreaker ($59.99, SoftComfortShoes.com). This Western-style bootie stays young and fun with golden double zippers. But the supportive Memory Foam and cushioned insole keep things practical and comfortable. Choose from British tan (pictured), dark brown, black, stone, or taupe, and wear with almost any style of jean, legging, skirt, or dress.
The "Rainy Day" Shoe
A tall rain boot can help you weather almost any storm, but an ankle-cut version like Vans Chauffette MTE ($57, Vans.com) is much less of a hassle to put on when you're stumbling out the door with a baby carrier and diaper bag. These foul-weather shoes are just like duck boots but without the cumbersome leg to slow you down. The nautically inspired silhouette and traction features are super sporty while water-repellent leather and synthetic uppers keep feet dry all day long. There's even a heat retention layer between the sock liner and outsole so you're not freezing your toes off while waiting for the C train.
The "Running Out the Door" Shoe
Your kid's colorful kicks won't hold a candle to the vintage-inspired Reebok Classic Leather HH ($80, Zappos.com). When you're short on time (cutting off those pesky PB & J crusts, for instance) and still want to look stylish, lace up these trainers alongside your standard black leggings and they'll make any Tuesday morning feel downright peppy. You don't have to be a runner to appreciate the utility of the high-abrasion rubber outsole (for durability and traction) and die-cut EVA midsole (for cushioning and stability).
The "I Finally Got A Pedicure" Shoe
You snuck away for 30 minutes to get a pedicure – congrats! Now show off the goods well into fall with the Coolway Jasper ($69) nearly flat booties. The open toe feature is both trendy and unexpected on these cutout, ankle-high shoes. And the side zipper closure means not having to Pilates reformer your feet into place when your kid is already late for karate. Choose from five different autumnal hues (though we tend to favor the burgundy) and pair with black jeans for casual occasions or a leather skirt for that work dinner you need to dominate.
The "Weekday Commute" Shoe
Whether you make two train transfers and then hop on a bus or simply skip over to your local coffee shop with your laptop in arm the OluKai Waipahe ($120, OluKai.com) will make your daily commute less of a footache. This modern Chelsea style has elastic gore for pulling on and off with ease, a rubber outsole for navigating slippery sidewalks, and a soft moisture-wicking microfiber footbed cover that can be removed and washed whenever needed. Plus, they're so much cooler than typical commuter sneakers.
The "Time To Cuddle" Shoe
It's time to put away your canvas and chambray Alpargatas and pull out the cozier kicks, like the TOMS Birch Sweater Knit ($59.95, TOMS.com) designs. These vegan slip-ons have a faux shearling lining for maximum comfort and peace of mind. Wear them around your apartment between kiddie cuddle sessions, or to the corner store for quick snack runs. A cotton twill sock liner, molded removable insole, and rubber outsole will keep your feet relaxed and protected. And buying a pair of TOMS means a child in need will get a new pair of shoes too via One for One.
The "Working Late" Shoe
Late nights at the office can throw a wrench in your family's schedule. Keep your cool by stepping up to the plate in the Naturalizer Emiline ($89, Naturalizer.com) loafer. This menswear-inspired slip-on is tailored with a round toe and subtle stitching detail. The look is entirely work appropriate for almost any office atmosphere with a half-inch heel. And a non-slip outsole means you'll still be stable when walking in the door post-bedtime.
The "I Need A Splurge" Shoe
What mom doesn't deserve a splurge that'll last longer than her all her children's combined years of teething, potty training, tantrums, and preschool? The Frye Melissa Seam Tall Boots ($398, Orvis.com) pair vegetable-tanned Italian leather with an equestrian sensibility that'll stand the test of time and trends. Leather soles and leather-lined uppers and footbeds make these boots utilitarian and durable, while staying versatile for pairing with all styles of pants and dresses.
The "Here Comes Winter" Shoe
Crosswalk slush puddles don't stand a chance against the Kamik Starling ($119.99, Kamik.com) winter boots. A plush foam and fleece insulation with waterproof DriDefense membranes will keep feet thoroughly protected in this highly functional ski-or-street-ready style. The CITYLITE synthetic rubber outsole with comfort EVA midsole and a reflective NiteRays patch make these boots indispensable when days are shorter (after-school = after-dark pickup?!) and temperatures dip. They come in chocolate, khaki, black, and charcoal for pairing with any color winter coat.