Comfy Dress Shoes for Grown-ass Women

I know I am not the only woman who, once she became a Grown Woman, realized her feet could no longer handle the spike heels, pointed toes, and cheaply made shoes she rocked through her 20s (and maybe her 30s and 40s). Plantar fasciitis, bunions, nerve damage, or just feet widening with childbirth and spending Lockdown barefoot or in Birkenstocks, our feet may not be as invincible as they used to be. But that doesn't mean we're forced into a lifetime of frumpy shoes. Below, I share comfy dress shoes for grown women, perfect for the holiday season and beyond. And knowing me, trust these are comfy shoes that are still chock full of style.

Comfy Dress Shoes for Grown Women

I've had fussy feet for most of my life. A toe walker as a child, I grew padding on the balls of my feet and the bottom of my toes with muscles built in unusual places. This gave me wide feet, wide ankles, and thick shins. Spending almost a decade working in retail, styling, and merchandising wearing trendy heels, I now can only wear heels to a certain height if the shoes have a block heel, and are well designed for proper balance of weight and cushioning and it needs to be a short night so I can take them off and get back into my Birks.

That being said, I have a passion for fashion, and as a short, curvy person, I love how many of my clothes look when paired with heels. But I also love a stylish flat shoe, as long as it is truly comfortable. Below are comfy yet festive shoes I have found that are worth your time and money for looking chic while feeling comfy.

Ros Hommerson is Quality Footwear with Comfort

I have a pair of black leather knee-high boots from Ros Hommerson that are older than my teenage daughter. The quality, the fit, and the comfort are unparalleled, but in recent years, I struggled to find more Ros Hommerson shoes and boots that fit my style. Ros has relaunched and gotten a glow-up with a gorgeous collection of truly comfortable and well-made shoes chock full of style.

Shop the collage: red platform strappy pumps | gold low-heel sandals | silver strappy low-heel sandals | black pumps with sparkly toe | black velvet loafers | gold closed-toe strappy low heels

Four widths, wide and extra wide calf options for boots, real leather and suede, and Ros Hommerson's signature cushioned Tiny Pillows insoles. Ros insoles have moderate arch support and help absorb shock while on your feet, but are also removable to accommodate an orthotic.

I personally own the Pammy (the red suede shoes in the collage above) and the Lydia (the gold low-heel sandals in the collage above, though in a different color), and they are amazingly comfortable and come in a width that let my toes wiggle and the balls of my feet relax with space. I am also impressed by the quality, which to me is nicer than a lot of the wide-width “comfort” shoes sold at major department stores.

Ros Hommerson Discount Code

Save 10% off at Ros Hommerson with promo code Oxygen10

Margaux Makes Comfortable Luxury Footwear in Widths

Margaux makes high-quality, stylish, yet not too trendy shoes. From ballet flats to platform heels, Margaux offers such footwear in high-end leather and textiles and a great range of sizes and widths. I purchased my first pair of Margaux heels in 2020 and now own three pairs from this quality footwear brand.

Shop the collage: gold ankle tie sandals | black mules | silver Mary Jane flats | lavender strappy heels | bronze platform heels | gold ballet flats

As someone who has wide feet, I appreciate Margaux's styles that transcend trends yet look fashionable and elevated. My three-year-old Margaux heels are still going strong, and I reach for these comfy dress shoes over any other pair in my closet, knowing I can walk and dance in them for hours. Other pairs I have bought since have the same quality and comfort. When I had an issue with one order, Margaux replied immediately with a personal response, remedying the situation the same day.

Ally Shoes Creates Comfortable Shoes for Work and Beyond

Whether you're most at home in a 3″ slim heel, or a lower block heel, or maybe you're more a boot or flat person, you must check out ALLY Shoes. As someone who rarely can wear flats, I find Ally's flats structured and supportive enough that I have been rocking the same pair for years with comfort and style. Ally Shoes has a range of heel heights and widths and even a bridal collection to show you can have comfy dress shoes for grown women that are fashionable too.

Shop the Collage: blush glitter heels, silver block heels, white Mary Jane flats with shimmer trim, red suede kitten heels, shimmery ankle strap block heels, gold flats

What I appreciate about Ally Shoes, other than being a woman-owned company that designs their shoes in collaboration with a woman podiatrist, is their commitment to great fit. With a range of widths and styles, Ally Shoes offers a Fit Finder quiz and free returns. To learn more check out my Ally Shoes review and my Ally flats review.

Ally Shoes Discount Codes

Ally Shoes has provided the Wardrobe Oxygen community a range of discount codes to save on their footwear. Use code WO2 to get 10% off sitewide. If you wish to try their heeled styles, promo code WO2HEELS will give you $40 off a pair of pumps at Ally Shoes.

Birdies Offers Stylish Footwear with Slipper Comfort

It's rare to find on-trend shoe brands that offer comfort, widths, and on-trend style but footwear brand Birdies provides all three. A popular shoe brand as well as a practical one, Birdies is a line of footwear for work, play, special occasion, and time at home. Birdies is a woman-founded B Corp company based out of San Francisco, offering flat shoes and slippers. And a lot of these flat shoes are luxe and dressy.

Shop the collage: magenta mule with puff | green velvet smoking loafers | sheer and beaded flats | black brocade flat with bejeweled strap | black brocade loafers with bejeweled detail | gold satin flats with bejeweled detail

I love a lot of Birdies shoes to wear with Le Smoking and other cocktail pantsuits and jumpsuits. They also look great peeking out of ankle- and full-length skirts and gowns. Birdies offers select styles in wide widths, as well as customization so you can have your shoes personalized. Each season they have fun patterns, textiles, and embellishments to update your closet with style and comfort.

Naturalizer Makes Dressy Shoes You Can Dance in All Night

As someone who likes stylish shoes but has fussy feet, I have relied on Naturalizer shoes for over a decade. I remember in 2017, attending an industry conference and going from dinner to a cocktail party, to a performance where we stood to watch, to dancing until almost dawn. I did it all in a pair of very cute Naturalizer heels. And I survived not just to tell the tale, but wear another pair of stylish shoes the following day full of standing and walking and dancing.

Shop the collage: burgundy metallic wedges | beige bejeweled strappy heels | black flat mules | black heeled mules | silver strappy bejeweled heels | hot pink metallic heeled sandals

I continue to rely on Naturalizer for comfortable dressy shoes, and appreciate how much of their selection is available in wide widths. Please note, the 27 EDIT collection by Naturalizer is not known for being as comfortable as the main collection, nor do the wide width options come as wide as Naturalizer shoes.

Repetto Shoes Were Designed for Dancing

Repetto has been around since 1947, creating dance shoes. Repetto became iconic streetwear shoes in the 50s by Brigitte Bardot and the 70s by Serge Gainsbourg. With designer collaborations through the 21st century, Repetto continues to be known as a stylish shoe that offers the comfort of a dance shoe.

Shop the collage: gold cross strap heeled sandal | black Lurex low heels | striped satin flats | silver strappy heels | red patent Mary Janes | blue-gray metallic oxfords

While I personally have not worn Repetto, I know many fashionistas across the globe rely on the footwear label for classically chic shoes for day and for evening.

Sarah Flint is Known for Elevated Comfort

Sarah Flint shoes are popular with attorneys and those who have to look elevated at work and spend a lot of time on their feet. With a range of styles and even more options of fabrics and leathers, Sarah Flint offers several options perfect for evening and dressy affairs.

Shop the collage: gold low-heel sandals | red kitten heel pumps | metallic flats | black strappy heels | lime mules | metallic pumps

I have not personally tried Sarah Flint shoes but have friends in real life who swear by the footwear brand for elegant style and true comfort for long periods of time of standing, walking, and dancing.

Other Brands that Provide Comfy Dress Shoes for Grown Women

Know this is not an exhaustive list of where to find comfy dressy shoes for us grown women. My focus was on footwear brands that offer an extensive range of comfortable shoes in formal fabrics and evening-appropriate styles. While one can wear leather shoes for dressy occasions, those are easy to find any time of year from most any retailer. This review focuses on shoe brands that carry comfortable shoes in evening fabrics or with dressy embellishments that elevate the footwear for evening and special occasions.

If you do not see what is your personal style aesthetic, consider checking out the shoe retailers below, which are known for quality shoes with comfort, and occasionally offer comfy dressy shoes:

• Vionic: Especially if you have plantar fasciitis or require arch support, Vionic has stylish shoes and some also come in widths.
• J. Renee: J. Renee shoes are great for those who like flair with their footwear. Offering fun colors, prints, and details, these shoes are also known for being comfortable.
• Aerosoles: While having an identity crisis every so often and changing their aesthetic and fit, right now Aerosoles is offering on-trend styles in on-trend finishes like silver mirror. I find they run more narrow than in the past, but still offer more comfort than a lot of department store brands.
• Walking Cradles: While Walking Cradles primarily focuses on footwear more appropriate to work and weekend, the brand occasionally offers dressier shoes appropriate for evening. I find the best selection of walking cradles at Zappos.