How to Spot “Old Lady” Shoes Before You Buy Them
The wrong shoes can, unfortunately, age your look, even if the rest of your outfit is on point. And while comfort is essential—especially for those of us who’ve sworn off stilettos—it doesn’t mean you have to settle for styles that feel more orthopedic than elegant. I’m sharing exactly what makes a shoe look like an “old lady” shoe and how to avoid those style pitfalls without sacrificing comfort.
The Tell-Tale Signs of “Old Lady” Shoes
When you’re shopping for shoes, it’s easy to get swept up in comfort features—especially when you’ve dealt with sore feet, bunions, or just the reality of being on your feet all day. But before you check out, take a moment to look at the style. Some shoes are quietly working against you, adding years to your look without you even realizing it. Here’s what to watch for.
Orthopedic Breathable Soft Shoes1. Clunky, Orthopedic-Looking Soles
Support is a beautiful thing—until it starts to look like you borrowed your shoes from a medical supply store. Thick, shapeless soles can weigh down your entire outfit and make your legs look shorter.
Try instead:
Look for supportive soles that blend into the shoe’s design. A well-constructed flatform or wedge can give you lift and cushioning without the bulk. You want structure, not bulk.
BZees Women’s Goody
2. That Boring Beige Leather (With Nothing Going On)
Neutral shoes are timeless… unless they’re bland, shapeless, and the color of a Band-Aid. If the shoe has no style details—no texture, shape, or polish—it can quickly veer into frumpy territory.
Try instead:
If you love neutrals, go for it—but choose a shoe with intention. Look for soft metallics, interesting textures like woven leather, or even a little hardware or trim to elevate the look.
3. Velcro Straps (Outside the Sporty Zone)
Unless you’re buying performance sandals for hiking or travel, Velcro straps are a red flag. They add bulk, break up the line of the shoe, and often make the design feel dated.
Try instead:
Look for styles with discreet elastic panels, sleek buckles, or zippers. If you truly need adjustability, some brands offer clever Velcro closures that are hidden from view.
4. Overly Round or Boxy Toes
Toe shape is one of those sneaky things that can completely change a shoe’s vibe. An overly rounded or boxy toe can make your shoes look orthopedic—even if they’re not.
Try instead:
An almond-shaped toe is almost always a safe bet—it’s flattering, timeless, and elongates the leg. If you like a square toe, choose one with a structured silhouette, not a stubby one.
5. Loud “Comfort Features”
You want comfort—of course, you do—but not when it’s the first thing people notice. Obvious rocker soles, clunky heel cups, or exaggerated arch molds can look more functional than fashionable.
Try instead:
There are so many brands now that build in incredible support without showing it off. Look for insoles that are contoured but discreet, and soles that are sleek, not orthopedic.
Examples of Shoes That Age You (and Better Alternatives)
Here are some common culprits to avoid if you’re trying to stop buying “old lady” shoes. Instead, look for their much more flattering counterparts:
The Bulky Mary Jane Flat
Skip: Cushioned Mary Janes with orthopedic soles and Velcro
Try instead: A sleek ballet flat with a strap or a modern Mary Jane in patent leather
Dream Pairs Walking Sandal | Nisolo Go-To Flatform Sandals
The Wide Velcro Sandal
Skip: Overly padded sandals with multiple Velcro straps and a rubber sole
Try instead: A flatform sandal with buckles and a cork or woven base
Orthopedic Penny Loafer | Sam Edelman Loraine Bit Loafer
The Plain Loafer
Skip: Super soft, shapeless loafers
Try instead: A structured loafer in patent leather, snake print, or a fun texture or color
Deborah’s Favorite Brands That Balance Style and Support
Here are a few go-to brands I often recommend for women who want shoes that feel good without looking frumpy:
- Vionic – Built-in arch support with stylish finishes
- Aetrex – Amazing for anyone dealing with bunions or plantar fasciitis
- Naturalizer – Classic and contemporary styles with comfort in mind
- Sofft – Comfortable block heels and modern sandals
- ECCO – Known for well-made sneakers and casual leather shoes
- Naot – Sleek leather sandals with footbed support
- Vivaia – Modern, chic styles with stretch knit uppers for softness
- Paul Green – Pricey, but worth it for supportive heels and tennis shoes that don’t look orthopedic
- Ron White – Fashion-forward, luxurious materials with a designer price but comfy
Quick Shopping Test: Before You Buy
When you’re standing in front of the mirror or scrolling online, ask yourself:
- Would I be excited to wear these on vacation or out to dinner?
- Do these shoes enhance my outfit—or just “go with it”?
- Are they giving timeless… or tired?
And don’t forget to take a full-length selfie if you’re unsure. Sometimes, you need to see the whole picture to know what’s working.
If you’re ready to swap frumpy for fabulous and say goodbye to “old lady” shoes for good, check out this post where I’ve rounded up some of the cutest (and comfiest) shoes that won’t age you one bit: Casual Shoes for Women Over 40
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I love your site and have passed it on to a number of friends. Really liked when you compared “old lady shoes” to more stylish! Keep up the good work!
Hi Jaysue,
You’ve made my day. Thanks so much for your vote of confidence. I thought that was a fun piece too! Glad you are part of the community and please let me know if you what you would like to see more (or less -Lol!) of. Cheers, Deb
Oh my gosh, Deborah, this is the most hilarious and helpful post ever! Hilarious – because you are so right, many shoe companies make frumpy-looking orthotic shoes when the same support and comfort can be easily accomplished with a stylish upper and a sole that doesn’t look like it came off of a tendinitis bootie. It’s so awful that it’s almost comical! I get women needing shoes that are kind to their feet (count me in!), but I haven’t met a gal yet who enjoys looking dumpy and dated. Worse yet, the same types of companies that make these frumpy orthotic shoes also do the same thing with wide-width shoes – they assume if you have a wide foot, that you don’t want to look pretty. Wide-width shoes are often as dumpy and unfashionable as poorly designed orthotic shoes. The struggle is real! Helpful – because you name the brands that do it right, and you show examples! The “skip these, try these” pictures are awesome! And you are so right; a shoe can really make or break an outfit. There’s no sense in suffering for beauty, but all women have the right to look and feel stylish and beautiful, even as their bodies age and require some care and attention. Not even old ladies need to look “old lady.” :) *dismounting my soapbox* Great post! Cheers!
Hi Carolyn, Glad you liked it. I did mention a few brands that are trying and have some decent comfort shoes but we need more!! and at better prices. It’s a great business niche for anyone willing to tackle it. I’ll keep looking and report as I find more. Cheers, Deb