Gen-X Approved: Your Guide to Chic, Non-Boring, Comfortable Shoes for Women in Midlife
We love footwear that nails both style and comfort — here are our 12 picks.
Looking for shoes that are both chic and comfortable can be a bit of a struggle — we've got you covered!
Our picks, shoes that are Gen-X Approved and curated by our awesome TueNighters community of women over 40, strike that perfect balance. Whether you're running around doing errands or enjoying a night out, our ultimate shoe guide will help you find the perfect pair that matches your style and vibe.
Note: Each one of these is independently selected by either you, TueNighters, or us, the editors. Things you buy through our links may earn us a commission.
Miz Moots Boots: Trendy Ankle Boots Giving Us Gen-X Vibes
These on-trend ankle boots will take you through the seasons in style! The low-cut silhouette pairs perfectly with everything from cropped denim to midi skirts, or wear it with leggings for an elevated casual look.
TueNighters are saying: Miz Moots boots that are as comfortable as sneakers. Also super stylish. I have several pairs and some are more comfy than others, and some feel snugger than others. — Rachel
Rothy’s “The Driver”: Hot Pink, Super Comf
These highly rated slip-on driving shoes in power pink are perfect for a tool around town or, of course, a Barbie premier. They’re knit from Rothy’s signature thread, which is spun from plastic bottles — so you’re doing good while looking fab.
TueNighters are saying: Super easy to wear — they pack a punch with black ankle pants or jeans. — Margit
Börn Shoes: Ageless Allure of Penny Loafers
The lugged sole penny loafer is crafted with signature Børn comfort in a multitude of colors. They’ve designed the Carrera in a rustic palette of nature-inspired hues in beautiful leathers and suedes.
TueNighters are saying: Börn shoes are Scandinavian and comfortable! — Kelly
Blundstone: Get Your Grip On With Slip-Resistant Lug Boot
Combining durability, functionality and style, the rustic black premium water-resistant leather is a modern take on a traditional deep ridge Lug sole — deep grooves designed specifically to increase slip-resistance in varied environments.
TueNighters are saying: Blundstone boots! Totally the best, most comfortable shoes I own. — Kate
J.Crew: Blue, Blue, Blue Suede Shoes, Oh Baby
Another penny loafer to add to our mix (you can never have enough). These are comfy and have that splash of delphinium blue for a bit of color. A lug sole makes sure these are all-day wearable.
TueNighters are saying: Love the color and the comfortable soles - you may need to size down a notch, these run big. — Margit
VIVAIA: You Had Us At Washable Ballet Flats
Not only are these ultra light but also flexible and comfortable for all-day wear. The doubled arch support helps reduce foot fatigue and discomfort, which makes these shoes ideal for your daily commute or a walk in the park. Also, check out Vivaia-Aria voted the best flats for plantar fasciitis.
TueNighters are saying: Highly recommend — Stacy London
Loeffler Randall: Fab All Weather Booties
On the pricier side but these are investment leather boots with a sturdy Vibram platform lug sole, for your rain or shine days. Super high quality and built to last.
TueNighters are saying: My friend Shelly had these boots and raved so I splurged, too. So glad I did; I wore them all last winter and planning to wear them again. Really fantastic, chic booties that you can walk a mile or two in. — Margit
Birkenstock: Snug and Fuzzy Fur-Lined Sandals
The legendary two-strap design from Birkenstock is now available in an extra cozy version thanks to a soft, genuine shearling lining on the anatomically formed cork-latex footbed and straps — these sandals are the ideal choice for older women looking for comfortable footwear.
TueNighters are saying: Super cute and comfy, even with a dress. — Amy
ECCO: Cute Kicks, Happy Feet
An essential everyday sneaker with on-trend retro detailing for versatile wear and their lacing system with pull tab allows you a customizable fit.
TueNighters are saying: Ecco shoes makes a cute sneaker with strong support - comes in lots of colors! — Nariah
FitFlops: Sunny Strolls in Ergonomic Sandals and Slides
These slides are elevated in every sense. Cool. Easy. Contemporary. Featuring premium, butter-soft, nappa leather, tanned without using chromium – making these both extra luxe and eco-friendlier.
TueNighters are saying: I always wear FitFlops, but the ones with micro wobble board technology. They are supportive and comfortable right out of the box, and your ankles won’t roll. — Tracey
TAOS: Simple Style With Casual Shoes
An everyday women's casual shoe gives your feet the arch and metatarsal support they need to run through your day's tasks. Zipper closures give you a great look while being easy on, and easy off.
TueNighters are saying: Anything Taos! Especially if flat-footed and no arch! — CJ
Birdies: Coming In Hot
There’s a reason these smoking slippers come in a bazillion colors and patterns and have 30k likes. They’re easy gliders with panache. The round-toe is bunion-friendly for us midlifers, too.
TueNighters are saying: Have these in the cheetah print but have been eyeing the raffia styles. You can’t go wrong with any of these colors. — Margit
Thank you for all these ideas! I have the Birdies Starling in green velvet and get so many compliments -- so comfy, too. I ordered another pair from ThredUp in a gray cloth, but they are a bit short in the instep. Going to try stretching them.
I have to say... I am deeply coveting the blue suede loafers, the spendy chunky boots, and the retro sneakers. I need to earn more simply for the love of comfy shoes--forget heels. It is a whole new era in my life.