How not to look frumpy in a clunkier shoe
Hi, Deborah and JoJami,
I would love your advice on how not to look frumpy when I have to wear clunker shoes because of foot problems. Because of an old skiing injury, I have been unable to wear heels since I was in my 20’s, which makes it hard to look and feel sexy, or even professional, when I want to dress up. I’m limited to certain brands of shoes recommended by my foot doctor and orthopedic surgeon so it’s not just a matter of being able to wear flats.
For example, I’d love to wear leggings this Fall as shown in the photo on your website, but I can’t wear heels.
I’d appreciate any advice you can give me. Many thanks!
- Nancy
Dear Nancy,
We sure wish we could wave a magic wand with your problem, but it is not that simple. However, your problem is one that many women face. We get letters all the time from women that can not wear heels.
That being said, you can still look fabulous but just have to try styles that might not be the latest trends.
The good news for you is that with styles changing so often, almost anything goes when it comes to pant styles.
When you are stuck having to wear clunky shoes, there are several things to make sure you do not do. First off, is leggings will be out of the question for you. Since the style is really a “pencil” shape, no matter what you do, legging will just not look good with a clunky shoe. Instead, you will need to opt for any pant that has a wide leg and (or) has some flair at the bottom.
This will still be stylish, and you can wear almost any shoe. Also, there are some great brands of shoes out there that do sell some comfortable shoes that don’t look orthopedic.
Here are some styles from Zappos.com that we suggest:
![]() These Taryn Rose flats are comfy and stylish |
Actually if you can wear this type of flat shoe you could still wear it with a skinny jean and look great! |
![]() This is good with pants only! |
Once you have to start wearing more orthopedic looking shoes like these, you can easily see that style starts going out the window. |
![]() Another simple but elegant choice |
However once again, if you wear these with the right style of well-fitted pants, you will still look great! |










I, like the other Nancy, also have foot problems and am limited to the type of shoes to wear. Although I love the look of heels, and the look of the ballet flat, neither one of them will work for me. I must wear shoes such as Bass, Dansko, clogs, etc. Shoes are ALWAYS an issue. I have found that with a straight cut pant you can get away with a clunkier shoe and still have the more current slim leg look. Even clogs can look stylish with this cut, in fact, European, if the rest of your outfit fits the bill. I have learned to wear whatever shoe I must with attitude!
Hi Nancy,
Yes, we feel your pain. Shoes are very important to looking chic, but if you have to wear wear only limited types,then you are pretty much stuck with wearing only pants. However, if you could find a comfortable boot, then your options would really open up for you. Do you have any short or tall boots that you can wear?
Please let us know and send us a photo. We would be curious of what choices you have out there!
I have struggled for awhile as to why flats are ok with skinny jeans but not leggings – as long as the shoes are not too orthopedic-looking. I’m 5’11″ with most of my “extra” height in the legs, so I’ve rarely worn high heels. Of course, I realize that means I can get away with lower heels than many women feel they can. But, who cares? If low heels are more comfortable, find some you adore & wear them with whatever outfit you want!
I found some hush puppies that are made of a stretch fabric that work for my foot problems & are holding up well – i.e., not stretching out to being unwearable (they also have a number of other styles that are cute & trendy these days). And there are other brands that use stretch fabric for all or part of the upper construction, so they are kinder to the foot.
lands end also has some comfy flats in cute colors that I’ve gotten lots of compliments on.
I agree with Nancy that it’s mostly about the attitude. Sometimes you’ve just gotta do what ya gotta do, so make no apologies!
Hi Ellen,
I think you have a good question and one that many might be confused about. Why are flats OK with skinny jeans and not leggings, is because, jeans have more weight to them and the leggings are so form fitting. I think the best example will be for us to take some photos so you can see the difference. Yes, attitude is important, but so is balance. If you want to be respected as someone that understands what is tasteful and good looking in the way your dress, you must be aware of how you really look. If you look out of proportion (e.g.with clunky shoes and leggings) then it is like a musician who is trying to play a song, but is really hitting all the wrong notes. Looking good in your clothes is a formula and we hope to encourage our readers to trust us!!
However you are right, in that attitude can play a part of that formula!
Thanks for your comments, we are always interested in hearing from our readers!
Hi, Glam Gals!
First, I have to say that while I’m sorry others of you out there are also afflicted with foot problems, it helps me to know I’m not alone! Because if enough of us are out there, that shows a need for a solution in the marketplace. And, Nancy, we sound almost identical in what we can and cannot wear.
I’m excited because I just got home from Nordstrom’s with a pair of boots I can wear! So far at least . . . Hooray! The brand is Miz Mooz (Bonnie) (www.miz-mooz.com). They’re flat (okay, a tiny, tiny wedge), shiny, black boots that zip up the back. I also ordered a pair of flat, black boots made by Cole Han that have a buckle on the side. Cole Han only makes one kind of flat boots, I’m told. It’s a sturdier boot that I think will also work well.
So now I’d love to see photos of skirts that I can wear with these. I also just posted this question to your contact address . . . I’m looking for casual, everyday skirts – not business or professional – but so far everything I’ve found is way too long or business attire. I’d like something shorter,a little sassy. And please remind me again, what’s the difference between tights and leggings?
I love your website!
Hi Nancy,
This is great news! You are going to find that your style has just shot up on the fashion scale!! We will look for some examples and post them soon.
One thing, you will want to make sure that the boots fit your leg well. It will help make finding skirts a lot easier. Also, always wear or take your boots to the store when shopping for skirts. Depending on the style of boot, and where the skirt hits, can be tricky. There is no hard and fast rules when it comes to the length of the skirt and the boot, but wearing matching dark tights (not sheer hose) will make the look complete!
Good luck!
Thanks for the tips about shoes. I don’t have foot problems but I love to be comfortable and fashionable. Ballerina Flats seem to be the answer.
Mary
Hi Mary,
Yes, they certainly can be comfortable, but don’t rule out anything with a wedge or platform…. they can give you a little lift and more choice of styles!!
What a relief to finally find a website that discusses this topic. After stress fractures, some other foot conditions, balance problems and now arthritis now require I use a cane and “prescribed” orthopedic shoes with lots of support and cushioning, dressing up has become a challenge.
I’m only in my early fifties, so I want to look as elegant as possible at my niece’s wedding in Oct 2010. So far, I’m thinking of wearing dark navy silk pants with a dressy magenta jacket (to help keep the focus to my upper body). There’s no avoiding the cane or “sensible” shoes unless I opt for a wheelchair, and that’s simply not going to happen, so it’s very encouraging to hear the opinions here. I was a bit concerned about appearing clueless or disrespectful by wearing what appear to be black athletic shoes, but I’m now inspired by the positive attitude shown by others here.
HI Rita,
Thanks for writing in. We do know that many women suffer from foot problems and yet still want to dress nicely. Your idea of wearing dark navy silk pants is a good idea because pants are always the best option when you have to wear a sensible shoe. Make sure you wear dark hose to match the dark shoes.
Good luck and enjoy the day knowing your smile will be what everyone is looking at, not your shoes!