when your feet finally say, “enough”

dressy flat shoes
Aren’t these Miu Miu jeweled heel flats fun and cheeky? You could wear with a dress or skirt, or with a modern tuxedo. Or yes, with your jeans.

My feet have been sending me a message and in recent weeks it’s become loud and clear. Every time I put on a pair of heeled pumps (even those I wore in comfort just a few months ago), I find I have to sit right back down and take them off. It’s not any one particular pain point; they just feel wrong. Whether a few months of wearing mostly low-heeled boots or wedges have spoiled me, or I’ve finally hit the Age of Finicky Feet, I think my days of wearing stiletto heels (even those under 3″) with impunity are over.

silver metallic loafers
Why not a pair of metallic loafers with those palazzo pants or a maxi skirt?

Because there’s little going on in my life that requires dressing up on a regular basis, this has been no cause for panic. I have plenty of comfortable and stylish low-, wedge- and block-heeled options in my closet that will cover me for just about any occasion. But as I’ve received a few requests in recent weeks for suggestions for dressy and special occasion attire, I thought I’d start, as I tend to do, with the shoes, and with an eye toward comfort.

cap toe pumps
Remember how Karl Lagerfeld sent all of the models out in a sling-back cap-toe shoe at the Chanel Fall 2015 RTW show during Paris Fashion week? Think Chanel and wear these with everything.

The good news is that flat, low-heeled* and block-heeled shoes are “in” (as much as anything is “in” anymore), there are a lot of options available, and the phrase “comfortable dressy shoes” needs no longer be an oxymoron. I’ve been reading Alyson Walsh’s new book Style Forever: The Grown-Up Guide to Looking Fabulous** which will be released in the US later this year and is currently available through amazon.co.uk for those on that side of the Atlantic or who don’t mind the shipping fees. I love her take on Casual Glamour, which means mixing up casual and dressy items, and wearing elements once restricted to evening at any time of day. So the other good bit of news is that those comfortable dressier shoes don’t need to be relegated to the closet in between Special Occasions; you can mix them into your everyday look. Suede (yes, even for summer now), patent leather, quilted, metallic, velvet and embellished finishes will read as more dressy than plain leather or some types of cloth shoes. I tend to shy away from satin as it can tend to look a little too Bridal Party™.

suede ankle strap wedges
These are my current go-to dressy shoes. You can bet they’ll  be in my suitcase when we travel to Europe in a few weeks. 🙂

I think it works in our favor is that the lines between dressy and casual have blurred somewhat. I’m not saying that means it’s OK to wear jeans to more formal event, but no longer does every item in an outfit have to meet the same stringent level of formality. In fact, I think it creates a more modern look when they don’t. The idea is to have the overall look read as dressy, without a matchy-matchy effect that borders on stuffiness.

Below are more ideas for low-heeled dressy shoes that would also work with casual outfits. I’ve included mostly closed-toed styles for maximum versatility but if sandals play a starring role in your footwear collection, there are many choices available in pretty lower-heeled styles. Even for dressy occasions, you don’t need to sacrifice comfort for style, and the more comfortable the shoes, the more you’ll wear them. I always advise adding a rubber half-sole to leather soled shoes both to increase lifespan and provide a bit more cushion and traction on slick surfaces. Likewise, check with your cobbler about replacing plastic heels with rubber.

Do you have a favorite style or brand for comfortable, dressy shoes?


*I actually find a bit of heel more comfortable and supportive than a completely flat sole.

**Which is so fun, informative and entertaining, and that I’ll be reviewing in more depth soon.
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30 Comments

  1. Fantastic! From Spring to Autumn I live in variations of the loafer or slipper styles, either flat or a minimal heel and of course the same for sling backs which is why I love your black ones so much. If I do wear heels (never more than 3″ anyway), I feel like I need to dress down everything else. What you say about having an overall look as reading dressy is so true and this is what makes dressing infinitely more fun these days.

  2. I discovered Thierry Rabotin in Paris. There was a shop on rue St. Jacques near Port Royal where they had the best selection of “comfort shoes” that I have ever seen. Cheap, flat ballerinas or loafers are not comfortable. I have a silver pair of Amalfi ballerinas
    that are comfortable and dressy. For a less expensive comfortable shoe, I discovered Bernie Mev . As I get older and I am walking a lot, I require a well-fitting shoe with cushioning.

  3. Ah yes, I’m remembering my early twenties, and wearing high heels all day at work, standing behind the cosmetics counter at Simpson’s here in Ottawa. Then walking to the bus and then three blocks home after getting off the bus. Oh the agony of da-feet, as my roommate used to say. Maybe that’s what prompted the decision to go back to uni and finish my degree?
    What a great idea to have the shoemaker add a rubber sole to leather ones. I have a pair of leather soled boots that I love, and which are treacherous in winter and early spring …even in my own back yard which has a slight hill on the way to my car. Love those ankle strap shoes of yours, especially with cropped pants.

  4. You prove that there’s style in every heel-height. Many of us don’t want to endure the pain of high heels, so we shouldn’t. And we can still find attractive shoes.

  5. Brava! Good call, Madame! It’s been flats for me for years, and my feet and back have thanked me. I’m very fond of Naot shoes: they’re comfortable and stylish.

  6. Thank you for your fabulous blog! Am wearing your blue/black theme to Paris in 2 weeks. May be forced to add black Born clogs for emergencies. Can I wear a black velvet jacket there in May?

    1. May I reply? Yes, you can wear velvet; I would add a white tee or shirt to “springify” it. If you can’t wear white, maybe a stripe with black in it or pearl gray.

  7. I am so with you on this one. I rarely wear heels these days or if I do I get to my destination in flats with heels in by bag for a quick change. I think a low block heel is the best. I am also finding that bally flats no longer give me enough support. I am reverting to some of my older but very good quality Tod’s. The time has come to spend a little more money on good quality. I can no longer get away with budget shoes.

    1. So true, Jo… it kills me to pay for some of the shoes that make my feet happiest but with care they also last far longer than cheaper ones.

  8. You have such wonderful taste in clothing AND shoes. I love your shoe choices but cannot wear pointy toes. Many of your shoe choices have been good ones for me but I can’t wear the pointed toe ones at all!

  9. I last wore high heels 1 1/2 years ago; my daughter talked me into buying a pair of divine, strappy, 3″ spike-heeled black suede sandals that were on sale at Coach in Las Vegas. I attempted to wear them to walk to dinner across the street (we were staying at Paris and were headed to Picasso in the Bellagio) and I got as far as the bridge that traverses the street before I had to say “STOP!” and then took off the heels and crossed the bridge with bare feet. I DID put the shoes back on to walk (slowly) through the hotel, but barefooted it again back to Paris after dinner. That was the end of my relationship with high heels; the shoes have been since passed on to the girl who talked me into buying them.

    I have two pairs of Clark “Sage Copper” (very low) heels and can wear those, but that is it, and like you, I do find myself looking for flats or wedges now. I LOVE those black, strappy wedges that you have, and may invest in a pair.

    I’m so glad you wrote about this as I am relieved not to be the only one to have to leave pumps behind. I love the J. Crew look (jeans + pumps) but am going to have to leave it to the younger ladies. Oh well, there is much to be said for comfort!

  10. I do wear higher heels but also mid or low heels – as you said they tend to be more comfortable than completely flat ones. It just depends on the occasion and whether I have to stand and walk a lot. Those silver loafers are gorgeous!

    Annette | Lady of Style

  11. I am so “on board” with this posting Susan! I love fashion, and I am continually trying to look cute and fashionable, even though I am only 5 1/2′ tall. I keep buying 3″ booties, and even higher sometimes (as long as they are platform with 1″+ soles) but at the end of the day, the tootsies sore 🙁 I keep trying… but resort to buying the cutest flats I can find as an alternative! Thank you for the samples for us to view. Appreciate your style!!

  12. I do not want to be one of those women who wear tennies with her nice clothes, but I also do not want to be in pain. Why is it that the only place I am losing fat from as I age – besides my face – is the bottom of my feet? I need my feet fat! I need it so I can wear pretty shoes and not suffer.

    I think those Chanel shoes are the key. Off to eBay to see if I can find them! (That is where I have found almost all of my Ferregamos, except for the one pair at the nice consignment store where they had them marked down to $11. “Nobody knows what they are here,” mourned the shop owner. I did.)

  13. It’s not just the feet, it’s the knees! I always remember French designer Claludie Pierlot’s remark abut why she is always in flats: “I don’t want to choose between my smile and my feet.”

  14. I think I am edging in the “to heck with heels” direction.” Kitten heels feel alright, because I can still move quickly in them. Heels just look alien to me now. Lost in translation.

  15. Yes, it happened to me overnight. All of a sudden my heels were of no comfort and no interest to me anymore. I never thought the day would happen, but my delighted daughter, who is the same size as me, is welcoming my extensive collection of heels. This now gives me another reason to start a whole new wardrobe of lower heeled dress shoes. Thanks for the inspiration and ideas!

  16. My feet failed me the day I turned 60. What I find most frustrating is the complete change in proportion – what used to work with heels doesn’t work (as well) with flats, so finding the right balance has been my challenge over the past 8 months. Good to hear I’m not alone in transition.

  17. With arthritis, I had so stop wearing heels of any height much younger; around 40 if I recall. However, like some of the commenters here, my most comfortable shoes have a low block or Cuban heel. My Josef Seibel Mary Janes like that are far more comfortable than any trainers I’ve worn. I bought three identical pairs (fortunately on sale) but the last that was presentable is starting to wear out, despite reheelings. So hard to find comfy shoes, and when I’m not cycling, I’m walking a lot.

    Lots of chic women wear flats nowadays.

  18. Flat shoes have been my choice for years, but I find I cannot wear anything completely flat – and now I need increasingly thick soles to be comfortable. Have pavements got harder?

  19. kande hall, I hear you! At 5’3″, I’m also always on the lookout for good looks at lower elevations. The short boots thing is great for us.

    My feet have always been a bit of a disaster area. First they are a difficult combination– quite small in size but with ridiculously high arches. I tortured them further for many years as a working stiff, wearing heels higher than I should have. Two surgeries later, finally got wise to that. I just wear heels now in tiny doses, and live mostly in flats, lower heeled boots (never sky high heeled boots– whats the point?), loafers and wedges.

    ann, your concern with getting the proportion right with your clothes when wearing flatter heels is the same as mine. Don’t you find that when negotiating that tricky terrain, if you keep the vamps of flatter shoes as low as possible, and the flatter shoes themselves as “un-clunky” as possible, that that helps the aesthetic?

    1. Yes! As well as the lower vamp, interesting colors, a pointed toe, and sling back kitten heels have also proved to lengthen my silhouette and help with the proportion issues. All in all, it’s a constant attempt to define an evolving style.

  20. I really like your suede dress shoes. They are quite fabulous. And the Chanel cap toe…I hae a pair of Adrienne Vittadini cap toes, camel with black patent leather trim & silver buckles. They are my personal favorite. I’m down to two pairs of heels. Just cannot wear them anymore. Personally, I think I could spend the rest of my life in flip flops. Unfortunately, the northeast only accommodates weather-wise about 4 months of the year.

  21. Hello; I’m french, 50′, and I love your blog: your Californian style is easy,”classe” and comfortable to wear. But it’s a little bit difficult for french to do shopping on Nordstrom( shipping and taxes are very expensive!) Dommage!(sorry for my english!!)

  22. Just received the black, strappy Belle by Sigerson Morrison wedges that I ordered through your link. Not only are they gorgeous and dressy, but they are surprisingly comfortable! I was concerned about the pointy toes, but somehow there is enough room in the shoe for my toes. They make me feel young and sassy! Thank you for writing such a wonderful blog and sharing your excellent eye for fashion. I try to buy things through your links to help you maintain the blog. I know how time consuming these postings are.

    1. Aniko, I’m so happy you like them! Thanks so much for taking the time report back, and I hope you get much enjoyment from wearing them.

  23. Fabulous selection of shoes. I couldn’t find the Wallace black multi suede shoes online – alas, they must be sold out as they are soooo gorgeous!

    Monica.