Close this search box.



I’m still wondering what possessed me—last week—to pair that gorgeous, Whistle River, black lace skirt with a pair of kitten heels that hurt my feet. Probably because I still long for the days when I wore heels with almost everything. But kitten heels? Two years ago I was embarrassed to be seen in kitten heels. Now I can’t handle them for more than a few minutes.

When it comes to the evils of aging, I rank painful feet up there with saggy jowls, thinning hair and a vagina as dry as granny’s drawers.

As part of my continuing series on Building an Over 50 Wardrobe, let’s look at one of the fundamentals of every wardrobe… Smart, comfortable footwear.

I was never one of those women who went crazy over shoes, purses or jewelry. Just cameras… What can I say? Something must be wrong with my DNA, but I’m working on it. As long as I have the basics, I’m happy. 

Here are the different types of comfortable footwear that will go with most anything in your closet 

…and a cautionary tale.


A pair of black flats and a pair of leopard flats will take you most anywhere. Leopard is the new neutral and looks great with almost anything, plus it gives you that certain “Je ne sais quoi.” That certain something. In the shoes below I’ve also included a dressy pair of flats with a crystal brooch. THEY’RE GORGEOUS!

Ballet flats are very Audrey—and men think they’re sexy—but let’s not forget loafers. I particularly like these Paul Green Uptown Loafers. BTW, Paul Green is on my list of comfortable shoe brands, provided by all of you, dear readers. In case you missed the list, here it is again.

When buying flats make sure you have a comfortable toe box. That means no pointy toes unless you want to signup for hammertoes. As we get older mules or slip ons also cause hammertoes and get harder to wear and make us less stable on our feet, because they force our toes to curl and grip in order to keep them on. 


Ankle boots are so versatile. A comfortable pair of black ankle boots and a neutral pair, like tan, is all you need. They can be suede, leather or sporty lace ups, and if you’re not comfortable in heels, try one of the great flat boots, moto boots or ones with block heels.

I’ll leave it up to you whether you want taller boots that reach your shins or up to your knees. Taller boots—especially when worn with leggings and pants tucked inside— “dissect” our figures at what can be unflattering places… especially if you don’t have long legs. In other words, not everyone looks good in tall boots.


It took my design eye a little while to adjust, but I think sneakers with thick, white soles look great with almost everything. The key is what color sneakers you wear. I think we all need three pairs of sneakers: blush, silver and black. These should cover everything from summer to winter, casual and dressy. Yes, even dressy!


Sandals don’t offer your feet much support, and flip flops are about the worst thing you can do to your feet. Even if you’re wearing thick-soled flip flops, don’t make them your primary footwear. 

Like mules, sandals that have just a band across the top of the foot can cause hammertoes because they force our toes to curl and grip in order to keep them on.


If you have hip, knee, back and/or balance issues, wearing flip flops and sandals can be dangerous on uneven terrain. The toe end of a girlfriend’s thick-soled, flip flops got caught on the ancient cobblestone streets of Florence, and she did a face plant onto the stone. With blood everywhere, front teeth in hand, two ambulance rides and two hospitals later… She also discovered she had a broken jaw. Not a great way to start off an Italian vacation!

Share this Story

Hi Girlfriends,

I’m proud to say that 1010ParkPlace™ has been voted one of the Top Ten Blogs for women over 50: the best-educated, wealthiest, most powerful demographic in history.

Here you will get a glimpse into the lives of other women, learn how they handled things life put in their path like divorce, the death of a spouse, serious health issues, low self-esteem, addiction and how to reinvent yourself after a major life change. You will find like-minded women and relevant conversations about finances, fashion, sex, books, music, films and food. We feature interviews with inspiring women along with straight-talk and bold conversations to reawaken your passions and make life count.

Brenda’s Blog has between a 58.4% and a 68.7% click thru rate, which is unheard of. My readers tell me it’s because I’m sassy and transparent, they trust me and no topic is off limits.

Tell your girlfriends, sisters and coworkers about 1010ParkPlace. We have lots of exciting interviews planned and stay tuned for updates about my memoir! 

#WhereStyleIsAgeless   #MakeLifeCount   #WhatAreYouWaitingFor


  1. Could not agree more re: my disappointment at how my shoe options have narrowed as I age. But I also think the market has responded to us with cuter comfy shoes. Still I miss my heels now and then, and it’s comforting somehow to know I am not alone.

    Cobblestones are treacherous even in sneakers. I, too, did a sidewalk face plant in Italy at a cobblestone/concrete transition point. I ended up with a concussion in the ER in Rome. Luckily, I had no broken bones or teeth but it was very frightening. And we were at the end of our trip. All in all, we felt very lucky. (I was able to rally for a day of shopping before we flew home. Haha)

    • Laurel, Woah! You did this in sneakers? A concussion is scary enough when we’re home with access to our own doctor but in a foreign country with language issues and not knowing whether you’re in a good facility? Brave woman to keep going… shopping! HaHa… I now look at the older women in my life with more sympathy. They didn’t have “cute options,” just orthopedic looking shoes. Their feminine spirits must have been crushed. I hope our options continue to improve. Thanks for sharing your story, Brenda

  2. Your poor friend! Did she not realize the dangers of cobblestone streets? I always wear a lace up shoe when touring for the support and comfort.
    I now own one pair of black, leather heels that only come out of the closet for dressy occasions. Comfort has trumped high style at this stage of life. I do still look at beautiful heels with envy in my eyes but no, they are not for me anymore.
    I tried to order the blush pink sneakers but they are out of my size.

    • Hi Joanna, I’ve stopped going into the shoe departments. For starters, there are very few brands that make narrow widths and then there’s the “envy factor.” I can’t wear any of these anymore. I want to see more photos of fashionista/famous women over 50, 60 and 70 and what they’re wearing. Sorry to hear the blush sneakers are not available in your size. Try googling “blush sneakers.” Perhaps you’ll find another pair you like. If not, wait until spring. They’ll be back! Thanks so much! Brenda

  3. So many shoes… and so little closet space, you Temptress! I am becoming even more finicky about shoes since my feet are beginning to hurt. I dislike going barefoot unless it’s on a lawn or the beach. What a change! I’ve been thinking I may go back to clogs (nurses and surgeons stand in them all day!) but I’m liking the thicker white sole on sneakers, and I’m certain I need a pair of both those Blush and black ones.
    Thanks for the inspiration!

    • Hi Donna, You really have limited closet space!!! Clogs… I’ve never been a fan of clogs. The wooden ones look uncomfortable and the rubber ones… just not my style, but sneakers… Yes! It’s taken a couple of years, but not only do I like them, I think they look great with even dressy outfits. I’ve been having trouble finding narrow sneakers to fit me or I would have worn them with this pretty, black skirt. We need to both buy a pair and have a “Show us your shoes” photo shoot at Christmas. Do you know that request? The Queen and her Court of San Antonio’s annual Fiesta are front and center at every event. Their dresses weigh 30 pounds, and since no one sees their feet, they wear sneakers or cowboy boots. The crowd at the Battle of Flowers Parade always shouts “Show us your shoes,” and the girls pull up their gowns and stick out their feet. It’s fun! xoxo, Brenda

  4. I am finding that some ballet flats hit “my bunion” joint in the wrong place…and I don’t have bunions! But they cut in just above the joint and so I can’t wear all ballet flats. Any suggestions? I found a pair of vionic flats with ortho insoles for my plantar fasciatis….great shoe! And, have it leopard!

    • Hi Melmi, I have the same problem with some flats… not just ballet flats. It all depends on how the shoe is cut, and it varies from manufacturer to manufacturer. I hobbled around NYC in a pair of Stuart Weiztman flats that were cut wrong and rubbed me raw. That’s the pits! The only thing I can say is keep looking and send them back if they don’t fit. I bet your leopard shoes look great! Good luck, Brenda… PS: I need to follow my own advice and look for some comfortable shoes that fit me right. It’s been on my “to do” list for weeks. I just keep moving it to the next day!

  5. I haven’t worn heels for about 7 years, I feel off my shoes and broke my foot and that was the end of my heels wearing days. I wear a lot of Keds and Sketcher sneakers. I like some flash so a number of my sneakers sparkle.

    • Victoria, “Fell off you shoes!!” That’s been my fear for over a decade! Fortunately that hasn’t happened. Sorry you experienced that. I love Kids and Sketchers. I love the flash as well. I included a pair from Anthropologie that are flashy but see they’re now sold out. Foo! xoxox, Brenda

  6. I’m all about the comfort in my shoes! Not to say that I don’t go for the look – I do. But when you’re 58, have always had foot problems, including two torn Achilles’ tendons (several years apart), you prioritize. Great choices, Brenda!

    • Thanks, Val! Two torn Achille’s tendons… Ouch! I don’t know what that’s like, but a too high arch in a pair of custom cowboy boots permanently messed up the nerves in the ball of my right foot and wearing shoes… period… has been painful since I was 48. I’m glad you like my choices because I actually thought of you when I chose the tan, ankle booties, thinking this would be something Val would wear. xoxox, Brenda

      • You are so right-on about the tan ankle booties! Ugh about your foot neuropathy. Foot pain is no joke – we’ve got to use our feet whether they hurt or not!

  7. I don’t miss the days of teetering around in sky high heels … all day at the office and Inyo the evenings. Ugh! That said, I now love in an area where Berkinstocks with socks seem to be the thing for women our age. No, thank you. I recently bought the most comfortable pair of Steve Madden leopard flats WITH a pointy toe but they’re so roomy and comfortable they’re row my favorite shoe!

Comments are closed.


Sign up to our list and we’ll send you our sought-after guide “50 Ways To Change Your Life”
I'm happy you've joined us! If you like what you read, I'd love for you to stay and subscribe to our updates by email. We have a great community of like-minded women, and your presence can only make it stronger.