Fight the Frump: Shoe Edition

Fight the Frump: The Shoe Edition | Footwear mistakes you may be making and how to fix them.

We’re back with another Fight the Frump post and this time it’s all about shoes.

Beyond wearing the wrong bra (more on that to come in my next Fight the Frump post) I think frumpy shoes are probably the biggest area where women make fashion choices that can age us unnecessarily.

This is partly because we tend to get stuck in an era and never move out of it. The trends that were popular during that era are going to look out of style and frumpy as time marches on. This is true for many aspects of fashion — hair styles, glasses, makeup, and most definitely shoes.

The other reason shoes are such a big issue as we age is our feet tend to get more finicky and we can’t wear all the flimsy shoes and high heels that are more flattering and stylish.

Even though I’m not there yet, I had a series of foot injuries a few years ago that relegated me to “comfort shoes” for quite some time. For a girl who loves her high heels and strappy sandals, it was downright depressing. It was also a great learning experience because I had to figure out what made a shoe frumpy (or not) and seek out the best of what was available in the realm of comfort shoes. (I’m also much more grateful for the ability to wear pretty much any style of shoe I want! It’s amazing what we take for granted until it’s taken away.)

Whether you need to wear comfort shoes or not, if you’re trying to fight the frump and keep your style current, assessing your shoe wardrobe is a good place to start.

Footwear Mistakes You May Be Making

Here are some common footwear mistakes women make and how to fix them:

#1. Wearing shoes that are too clunky.

I hesitate to post a “wear this, not that” type of graphic because no matter what I pick, I’m sure to be insulting someone’s shoes, lol. And as with most matters of fashion, it’s relative. Shoes that I wouldn’t be caught dead in might be a good choice for an older woman or someone with a different style aesthetic. But here’s one quick example that I think illustrates my point. These are both “comfort sandals” by the same brand, and they both serve generally the same purpose, but the one on the left looks more youthful and flattering because it shows more of the foot and has a more flattering vamp (that’s the material on the top of the shoe). Also the cork footbed is lighter and more on trend.

Generally speaking, shoes that are clunky are never going to be as flattering as something more strappy and delicate. Of course, sometimes shoes are purposefully designed to be chunky. In that case, you have to be very selective about what you wear them with so they look intentional and not like a fashion faux pas. But when it comes to fighting the frump, going with a more delicate shoe option is usually a good choice.

#2. Wearing shoes that are out of style. 

This should go without saying, but shoes can really date your look, which is always going to equal frumpy. I’m certainly not suggesting you replace all your shoes every season or follow every trend that comes down the pike, but keeping an eye on current trends and knowing what is in and out of style is important if you’re going to keep the frump-monster at bay.

I recommend going through your closet at least once a year (I do it with each change of season) and performing a ruthless wardrobe audit. Take all your shoes out of your closet and go through each pair and ask yourself these questions:

  • are they in good condition? (If not, donate or find a good shoe repair shop.)
  • do they fit my current lifestyle?
  • are they comfortable?
  • do they make me feel good when I wear them? do I love them and want to put them on right now?
  • are they still in style? (If you’re not sure, ask a friend you trust.)

With each pair of shoes, if the answer to any of those questions is no, it’s probably time to part with them. If they’re still in good shape, donate them. Otherwise, there are places that recycle old shoes. I did a quick google search and found plenty, but you may want to do your research and make sure you’re donating to a cause you feel good about supporting.

#3. Matching your shoes to your hemline.

This isn’t a no-no, but it’s not necessary, and it can make your overall look dated if you try to match your shoes to your hem too often. Try a contrasting shoe instead for a more modern look.

There is nothing wrong with the black pumps and the black dress, but the nude strappy sandals are more modern and of the moment. And I would recommend also experimenting with metallic or a bold color when wearing a black dress — or even a colored dress.

P.S. It is also not necessary to match your shoes to your handbag.

#4. Wearing hose with sandals or peep-toe shoes. 

No, just no.

I understand wanting to wear hose for certain occasions (I’m not against hose per se) but they should not be worn with sandals or open toe shoes. (I have an entire post on what hose to wear with a cocktail dress if you’re interested.)

#5. Wearing shoes that don’t flatter you. 

Most of us realize that we need to wear clothes that flatter our bodies to look and feel our best, and the same goes for shoes. Part of fighting the frump is learning what looks good on you and what doesn’t, and wearing what flatters you.

Women with skinny ankles and calves may look off-balance in a chunky platform sandal. Women with bigger calves and ankles should generally avoid shoes with a delicate ankle strap. If you have short legs, you probably want to wear shoes with a lower vamp, especially with pants and longer skirts. (Imogen Lamport has a great article on shoe vamp, if you’re interested in learning more.)

#6. Wearing shoes that are worn down. 

If your shoes are still in style and you like them, a cobbler can replace a heel or repair scratches and stains. Wearing shoes that look beat up or with a heel that is worn down will make you look sloppy and thus more frumpy.

Going along with that, make sure to take good care of your shoes. I cringe when I hear people say their shoes are in a heap on their closet floor. I have mine on shelves, and I keep some of my nicer ones that I don’t wear as often in their boxes. I have a pair of Stuart Weitzman suede pumps that I’ve had for almost 15 years and they still look like new because I keep them in their box with a little suede brush that I use on them every time I put them away. Doing this keeps them from gathering dust and and from getting marked up rubbing against other shoes in my closet over the years.

I don’t do that with all my shoes, of course, but with my really nice ones. I also take my boots to the shoe repair shop at the end of every season to have them cleaned up, and then I store them in their original boxes for the summer so they don’t gather dust.

Keeping your shoes in good shape protects your investment and helps you fight the frump.

#7. Wearing shoes that don’t fit. 

If shoes are too big or too small, that’s going to add to the frump factor. I have very squared-off toes, and there are some sandals I simply cannot wear because the footbed is too pointy and my toes will flop over the edge. This also happens when sandals are too big for my narrow feet — my feet slide too far to the front and my toes go off the end. NO NO NO. That is always a bad look. The same goes for stuffing one’s feet into shoes that are too small. It just doesn’t look good. Make sure to buy and wear shoes that fit your feet properly.

#8. Wearing the wrong shoe for the occasion. 

Running sneakers are great, but they belong in the gym or at the very least in a very casual environment with a trendy athleisure look. For the love of all that’s fashionable, please don’t wear athletic sneakers with khaki capri pants. (Try Converse or Superga if you want the comfort of a sneaker.)

Plastic flip flops are awesome for the beach, but they’re not the best choice with a sundress for church – at least not once you’re out of middle school.

Wearing shoes that are too casual for the occasion will definitely add to the frump factor, so unless you’re required to wear sneakers for medical reasons, try to match the style and formality of your shoes to the occasion.

#9. Wearing shoes that don’t work with your pants (or skirt/dress/shorts/etc.)

Sometimes you can have a great pair of shoes but they just don’t work with the length or style of your skirt or pants, and this can make you look frumpy. It takes some practice, and this is where Pinterest and fashion blogs can come in handy, but learning what style of shoe works with the various pants/skirts/dresses in your closet is a large part of fighting the frump and keeping your look current.

This is where I have to plug the Adore Your Wardrobe course once again.

I have spent so much time over the years trying on different shoe and pant/skirt/dress combinations to figure out what works and what doesn’t, and while I could sense a good combination and a bad combination, I never really understood WHY they did or didn’t work until I took the Adore Your Wardrobe course last year.

Getting dressed and putting outfits together still takes some trial and error, but much less now than it used to because I’m armed with the knowledge I need to put pleasing combinations together.


Whew! I had no idea I had that much to say on this subject until I started typing. I hope this is helpful. Feel free to share your thoughts and other suggestions in the comments!

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67 thoughts on “Fight the Frump: Shoe Edition

  1. I am such the shoe girl…not that I just like them and buy them, but think they can be that one factor that makes or breaks an outfit. I see so many older women at church with a great outfit until you get to their footwear. And I totally get the comfort factor, but I think that manufacturers are doing a better job with style and comfort now!!
    I loved that you showed the nude vs black shoes with the black dress. We even did a post about this earlier this summer. I called it classic vs modern with our shoes. Like you said, it’s not bad per se….just somewhat dated.
    And the hose thing….my mom (the 70+ model on my blog) has such a hard time going without hose because she likes her legs covered. But she has found some toeless hose that work with her peep toe shoes!!
    Fabulous run down, Jo-Lynne!!

    1. Wolford makes some great tieless hose, my friend wears them with everything. i haven’t tried them yet, but want to!

  2. Great post, JoLynne! I have an event soon and will try nude or metallic sandals with my mostly black dress. It takes a village…

  3. So very informative! There were a couple of things you pointed out that have definitely been a struggle for me. I knew they didn’t work, but I seriously thought it was just me being too picky. Also, I’ve never once considered the vamp to be a factor. This was so so helpful, thank you!

  4. Living in FL all you see is plastic flip flops ugh or on the older snow birds tennis shoes with their capris ugh again. The only time you will see in plastic flip flops is when I am coming out of the saloon from getting a pedicure and I am like you tennis shoes belong in the gym or a the theme parks . For my running up town errands I have Sperry shoes love them, and the rest of my shoes are similar to the ones you wear. I do not like matching same color shoes with my outfits like to pop the colors. I did think of one thing for your fight the frump post which I like, purses, I love to carry over size bags, but sometimes they look weird I have the entire top shelf of closet full of purses can you help with that. Thank you for all the fashion tips

  5. Thank you for another useful post! I am always on the lookout for stylish shoes that run narrow or come in a narrow width, so if anyone has recommendations I’d love the help.

      1. Thank you!

        I read your post on hosiery, and it was helpful as well. Did you try the nude fishnet type, and if so, would you please share your thoughts concerning them?

  6. Great post – gives me lots to think about for fall. I am looking for a shoe repair place, as I have two pairs of shoes where the heel has gone, but they are still in good shape. I really liked the look of the nude shoes with the black dress – I honestly never would have thought of that. Thanks!

  7. Very helpful post, Jo-Lynne – and you’re a great writer! You make blogging look easy but no-thank you-very-much, I’ll stick to reading them! ???? It has to be a lot of work. Have a great day!

  8. This is an awesome post and so very helpful! I am guilty of owning a pair of those clunky black sandals under the “Not That” label in your first pic and I felt guilty getting rid of them because of what I paid. But then my dog ate one of them and that was the end of my guilt trip! You have inspired me to go through my closet today and get rid of all my frumpy shoes. Thank you, Jo-Lynne!

    1. OH NO! See, I knew if I picked an example of a frumpy shoe, I’d be insulting someone’s shoes. Maybe your dog thought he was doing you a favor. 😉 Just kidding. They are fine, there are just so many better options, that’s all. 🙂

      1. No, you didn’t insult my shoes! I actually wanted to get rid of them so yes, my dog did me a HUGE favor! I completely agree with you that there are so many better options that are stylish and comfortable. Again, this was a great post and so informative!

  9. I really appreciated the tips on shoe/boot care as I can be in a rush to put things away and not as careful about how I store them…. That part of your post was kind of an “ouch”/ ” lightbulb ” moment…
    Over all, this was very a helpful post for me. I struggle a lot with shoe choices!

  10. Great information! Now if more shoe manufacturers will keep improving the style of shoes they make for those of us that have problem feet, and require specific things, it will be easier for us to not ruin an outfit with frumpy footwear.

    I keep all of my shoes and boots , even athletic shoes, in boxes due to space and closet design. But, that also makes it easier to change them out when the seasons change.

    Happy Friday eve!

    1. See I geek out over purging my closet. It’s the most fun I have all year. HAHA! I love the feeling of a freshly cleaned out closet that houses only things I love and can fit into right now. 🙂

  11. One thing that helps me keep my shoes organized is taking a photo of them & then taping it to the outside of the box. Most of my shoes are in plastic boxes but I also do this with the pairs I keep in the original boxes. I’m a visual person so it helps in planning outfits when I can “see” all my shoes. It also makes it easier to see what I need to get rid of.

  12. Awesome post!!! learned from Cindi earlier in the week to wear nude sandals with black dresses. All your information was great!!! Thank you!

  13. Fantastic post!!! Loved the commment about ill fitting sandals and wear a nude shoe with a black dress!! Now… how can we get this post out to women everywhere!!!!

  14. Informative and entertaining. I hate the matchy-matchy anymore. BUT, one problem I have is that most men don’t look at fashion the same way we do. I can’t tell you how many times I’ve done something similar to the black dress/nude shoe combo and had to explain to my husband (after his quizzical looks) it looks not only fine, but fashionable. He does recognize and appreciate that I dress a little younger than my age group peers (I’m 46), but he’s still a guy who doesn’t follow fashion. All this to say, well, I’ll just keep trying to catch him up. But I promise you if I left the house with the matching shoes/dress, he’d be telling me how great I look.

  15. I have to disagree with #4. Wearing hose with sandals or peep-toe shoes.

    I just can’t go without hose. My legs are too white and have blemish marks (veins etc) that I just cannot go without hose with a shorter dress. I also have tried self-tanning and even salon spray on tan but my pores are just too big and it looks awful! So I use the toeless hose that are made for sandals or strappy shoes. If I’m wearing jeans or maxi dress/skirt then sure I don’t wear hose. You ladies that have beautiful blemish-free tanned legs be thankful! LOL.

    But, as usual, all GREAT information! Thanks!

    1. Have you tried Sally Hansen’s Air Brush Legs? It Is essentially leg makeup but it stays put until you wash it off with water AND soap. It doesn’t budge with sweat, rain, etc. It comes in a lotion form or a spray form so you can choose your favorite. I don’t use it often but I’m always impressed with how well it works. It really does give an air brushed appearance to your legs that somewhat mimics the look of hose.

  16. Just did an edit of my shoes last month. One thing I did think of though, is sometimes in trying to fight the frump one might go to the opposite of the pendulum? I’ve seen older ladies in malls wearing high shoes or shoes that look great on a 20 or 30 year old but just make them look like they are trying too hard to look 29, you know what I mean? And I think where you are going also comes into play. Using your number 1 example, if I am going to the zoo or a fair or somewhere where I am going to be walking all day long on uneven ground I would choose the shoe on the right over the shoe on the left. It’s lower and I will not be twisting my ankle out or fatiguing my legs by wearing the higher wedge. That being said I will say that nothing screams frump to me more than Birkenstocks! LOL. I just cannot get myself to like any of their styles. Loved the advice on matching hem to shoe! And I am loving this little series!

    1. I agree about also not dressing too young. It’s a fine line.

      Now if I were going to the zoo, I wouldn’t wear either of the sandals I pictured here. I’d wear a Vionic sandal that is a little more stylish than the example on the right but lower than the example on the left. Or I’d just go all out with an athleisure look so I could wear Adidas Superstars or a sneaker that offers some support. I’m not sure my Converse would carry me through a full day at the zoo. 🙂

      Birks are… yeah. They are trendy and cute on the right person but I’ve never been able to embrace them for myself. I think this is when personal style aesthetic comes into play. You have to wear what you like and feel confident in.

      1. I will have to check out those vionics! I love the look of between the toe sandals but can’t wear them at all so I’m always searching for other options where I don’t look frumpy but they don’t kill my feet when I have to wear them for long periods of time! Thanks.

        P.S. enjoying all the comments on this post!

  17. Great post JoLynne! You put so much in to your posts and it is so appreciated! This post on shoes taught me more than a few things. Some I already (thought) I knew, but you confirmed! Thanks for keeping us all in line. Enjoy reading your posts every day. And I concur with another reader….it takes a village!

  18. A few years ago a friend clued me in about not wearing hose with open-toed shoes/ sandals, but I’ve always struggled with that because my legs are so pale. Just a few months ago I discovered Hanes carries a super sheer pantyhose that is toeless. It works GREAT with my strappy sandals and no one is any the wiser. My toes are bare but my legs aren’t!

  19. I love these Fight the Frump editions! I have a closet full of khakis and white pants-J.Crew, banana Republic, Ann Taylor etc. and I don’t know which are in style anymore (lengths, fabrics, pleats etc.). I would be great if you could consider this as a future topic!

  20. Excellent post! Since I’ve been following you, I have looked at a few other styles of shoes/sneakers. I’m stuck with a wide foot & my feet are half size difference.! Try getting shoes to fit that combo! Lol!! I love the look of your Chucks but found them too narrow. I ordered a pair of canvas Superga’s from LL Bean & they feel great, although one slips a bit on the smaller foot. I also found flats with a nice arch so I bought them in 4 different colors!! After seeing you in ankle boots last year, I gave them a try also & love them! My shoes are all in clear shoe boxes. I’ll wipe them out with a baby wipe from time to time before I put them away, as I don’t wear a sock with them. I love the no show socks for my sneakers. Like you, I go thru my “stuff” seasonally. I noticed I have 3 pair of sandals I haven’t worn all summer & they’re a few years hold. Out they’ll go! I do have 3 pair of frumpy looking sneakers that I was thinking I needed to keep but after this post, I don’t think I need to hang onto them!! This was the motive to move them on!!

  21. I am so loving this Fight the Frump series! I never really thought that the vamp applied to sandals too. Thanks for the information and taking the time to write these posts.

  22. Great series, JoLynne! I do have a question though. For fall or winter, with knee length skirts or dresses, I would like to wear opaque tights with them. If I don’t wear a boot, do you think it would look okay to wear a pump with a block type of a heel? Just want to be sure about what would look best! Also, one dress I have is a houndstooth that is navy/cream. Would a black boot be okay or just stick with a navy pump? Thank you.

  23. ????????????. I have those black Clark’s shown as what not to wear, and worse is that I have them in a cognac color too! I bought them 2 or 3 years ago from QVC. I usually only wear them at the beach with 3″ shorts and a tshirt. I am pretty sure I would never consider wearing them in a dressier environment. Wait until I tell my husband I have frump shoes! LOL. He doesn’t like them anyway, but he doesn’t have any interest I fashion. I guess I will donate those shoes. I also have a pair of blacknBirks that I love and wear in the evening sometimes to walk the dogs. I am a fashion mess with Clarks, Birks and shorts!????????????

    1. Hi Gina….a shout out to you, your comment made me lol!! I love Birks as well! ????. And if anyone is thinking of buying Vionics, they are amazing! I bought my first pair the other week, leopard print loafers & they ate the comfiest shoes I own., & hopefully stylish & not frumpy! ????????

  24. Thanks Jo-Lynne I am in C2 now and we are talking about vamp.

    I would say I am a shoe w…e but go through mine and after my knee issue had to purge.

    Curious what are the brand of shoes to wear?


  25. Boy Jo-Lynne, what an awesome post!!! I’ll be heading to my closet tonight. You do a really nice job on content both in quality and quantity. I make sure I alot quiet time to read your blog post without interruptions. I really look forward to them every day ????

  26. Great post! I would just add getting regular and professional pedicures or at the very least giving yourself a pedicure. Dry, rough heels and feet along with unattended toenails can make us look very unkempt and frumpy in sandals, etc. keep toe polish fresh and up to date as well.

  27. Hi Jolynne! This is your friend from Sydney, Australia! Even though I read your posts everyday I hardly ever comment but I had to today! You gave me the biggest laugh with your comment about wearing hose with open toe shoes…No, just no! Love it!! I’m still laughing. Thanks for the lol Jolynne! ???? Belinda xx

  28. I guess I should of waited a day before I contacted you about what shoes to wear. Thank you for another great post!

  29. Wow!!!! I have many shoes and they are just on the floor of my closet. I just don’t have room for all of them to be in boxes. I have most on wire low shelfs but even then they are stacked. UGH!! I have the hardest time throwing out my shoes and I take care of them enough they don’t wear out and I just hate if I thrown some out or give away and then end up wishing I hadn’t. Never fails the shoes comes back in style the year after I throw something out. 🙂 I agree with all your points. Shoes need to be current and I know when I die, in my eulogy somewhere it will say, “LOVED shoes.” 🙂 LOL I learned last year from Cyndi about not having to wear black shoes with a black dress. She usually always chooses nude. I like it better too. Thanks for all your hard work you do on your blogs. So informative. I’m like the lady above. I need quiet time to read yours. 🙂

  30. Being a shoe girl myself, I love all of these tips! However, I am a big fan of the recent trend of wearing socks or funky tights with sandals or open toe shoes! In fact, my post today features some wild openwork plaid tights with an open toe pump. And I felt quite sassy wearing it that way! So I guess rather than altogether rule out stockings with open toe shoes, there is a trendy funky way to do it! But definitely shoes can make or break the outfit!


  31. *sigh* … I’m green with envy for all of you ladies who can wear shoes based on fashion (as I used to). A chronic back injury has relegated me to shoes with only the most supportive of soles and absolutely no heel. If I am going to walk all day I’ll wear Asics running shoes with casual khaki capris because I’ll be bed bound if I don’t. Oh, how I miss the days of wearing lovely heels and shopping for shoes based on fashion. Comfort shoes have come far, but for me have not been able to compensate for my injury. I shudder to think what people must think of my shoe choices. I overcompensate in the handbag department:-))

  32. Good morning Jo-Lynne,
    Love your “fright the frump” articles. We all could use help with that…just wondering if you can do a “expunge your closet”? I’m sure we all have clothes in our closet that we need to get rid of, but don’t know how to begin. I sure could use the help and I would love to hear your ideas! Thanks,

  33. Love these tips! Thank you!
    YES YES YES to #4! Hose with open toes are such a no no!

    You also asked for requests a while back to this series..what about BRAS! Many women do not wear a proper fitting bra and they rarely get re fitted. Most people do not realize that a bra can make or break an outfit.

  34. Hi Jolene,

    I love your blog!  As a “fashionista from way back, I can say that you definitely have an abundance of great advice and tips!  I have a question about peep toe ankle booties.  I’m a tall 5’9” mid 50’s woman who loves clothes and shoes and I always try to look current and stylish while trying to look “appropriate”.  Which can be hard to say the least. Anyhow here’s the peep toe ankle bootie issue. Do you agree that it’s ok to wear a dark sheer toe / sheer or somewhat sheer hose with a dark peep toe closed back ankle bootie?  I tend to wear dresses a lot but with my long legs and as I’ve aged and my legs aren’t as attractive as they used to be I feel more comfortable with hose or tights. I love peep toe booties for their comfort and stylish look, but I can’t handle the look of my bare legs with a knee length dress. I’ve tried heavier tights and I think they are just a bit too much, but hose in the sheer side seem to look ok?  For the spring and summer I’m thinking of trying sheer open toe flesh colored hose. Any opinion or suggestions?  

    1. I’m so sorry that spell check changed your name, Jolynn!!  Also sorry that I didn’t catch this and fix it!  Please forgive the mistake. :-(. 

  35. I am plagued with plantar fasciitis and Achilles tendinitis in both feet as well as something going on in the forefoot. Basically my feet are done, and will be wearing “comfort shoes” for the foreseeable future. I spent the last year wearing athletic shoes or supportive sneakers (for the most part not cute ones) all the time. Even with skirts! My self esteem really took a hit. I need help finding attractive comfort shoes! I’m too young at 54 to look like a granny. Do you have any suggestions for brands?

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