Ask Allie: Wearing Heels

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Alison, you said you couldn’t wear heels after you had Emerson yet you wear them now, how did you get used to them again? I stopped when I gained a lot of weight but have lost 63 pounds on Medifast and want to wear heels again. Any suggestions?

How does one adjust to wearing heels? I see that you wear some sort of heel or wedge almost every day, and was wondering how you manage it? Do you use special insoles to cushion your feet? I desperately want to wear my heels more often, but after a couple of hours, can't bear them anymore. Any suggestions?

I don’t know if my advice will work for all women because I have a weird advantage – I have walked on my toes all my life. My relatives called me Tippy Toes as a kid, and I had to wear special shoes to fight against pronation and all sorts of other things that happen when you run around town on the balls of your feet. This is why I have such trouble finding boots to fit – walking on my toes not only built up my calves but also my shins and ankles. This is also why you will rarely ever see me in ankle-strap shoes. So walking in heels has never been a problem for me, I even wore 4” heels when working retail; I’d dash around 12-hour shifts on tile and concrete and do a few calf stretches behind the register while ringing up customers.

However, when I was pregnant my legs and feet swelled. A lot. A whole heck of a lot. By the end of my third trimester, I, Alison Gary, Crocs Hater was wearing my sister’s Crocs because they were the only thing that would fit (she wore two sizes larger than I). After Emerson was born, I spent the first few weeks barefoot or in sneakers because I was so unsure on my feet. Not only that, my feet permanently grew a half size, meaning all my lovely heels no longer fit.

wearing heeled shoes

When I knew I had to go back to the office, I purchased a pair of black ankle boots with a 1” heel. They were practically flat for the Old Alison, but the Postpartum Alison ended up with aching tootsies by noon. I decided to only wear them twice a week, and have those be days when I didn’t have to do a lot of walking. I looked into brands who specialize in comfort – Fitzwell who strategically places heels to have the least amount of pressure, Sofft who makes uber comfortable shoes that are also stylish. As I got comfortable with these shoes, I ventured into higher heels and different styles. I found that hidden platforms were a Godsend – I would look as though I was wearing high heels but they felt as though they were up to an inch shorter thanks to a platform in the footbed.

I stick to just a few brands for heels – ones that I know fit my foot well. If the toebed is too narrow or the heel is loose you will be spending much time clenching your toes just to be comfortable and keep the shoe on, which affects your gait and the comfort of the heel. For me, Vince Camuto, Nine West, and Sofft are safe bets for heels.

A shoe that stays securely on your foot will always be more comfortable. I love my Miss Sixty booties because they wrap around my foot – I can run in the rain and they will stay on. T-straps, lower ankle straps, Mary Janes, booties, caged sandals… all styles that will let you focus on walking and make the shoe more comfortable.

Almost every pair of shoes I own has a pair of Footpetals in it. Footpetals are very slim, but are very effective. They absorb sweat so your foot doesn’t slide into the toebox, and they offer a bit of cushioning making the heel wearable a couple extra hours. My favorite feature of Footpetals is that they collect the funk. Sweat, dead skin, gosh knows what ends up on the Footpetal and at the end of each season I pull them out (they have adhesive backing but are still easy to remove from the shoe) and replace with a fresh pair. Not only do they make the shoe comfortable, but they extend their life.

Before I wear a pair of shoes to work, I wear them at home. I put them on at the end of the day when my feet are swollen so they stretch out and I wear them while making dinner, putting Emerson to bed, watching TV. This way I can break them in and also get a true feeling for how they will feel for an entire day. If a shoe is too tight to fit at the end of the day, I try this process on a weekend morning. If the shoe is uncomfortable first thing in the morning when my feet aren’t swollen they go right back in the box and to the store – I don’t believe in a major breaking in process for shoes. There are plenty of shoes out there that are relatively comfortable right out of the box – give those shoes your hard earned money and save your time and effort for more useful endeavors.

Give your feet a break. On weekends I wear lower heels and flats. I rarely wear the same heel height two days in a row. I put my feet up under my desk to give the tootsies a rest. If shoes are really high or crazy, I will pack a pair of flats in my bag for the commute.

And finally… heels aren’t necessary to be stylish. There is many a stylish woman on this planet who don’t leave the land of flats. If you have foot issues, don’t exacerbate them with uncomfortable or inappropriate shoes. Your feet work hard enough as it is – don’t torture them. Sites like Maryland Square, The Walking Company, and even Nordstrom have amazing selections of comfort shoes, many that are right on trend and stylish. Blogs like Barking Dog Shoes review and feature comfortable shoes for women with all sorts of personal style.

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  1. Thank you a million times over for this post! I have suffered from an arthritic toe joint for over a decade and I really miss my heels. Thanks to you I have found Sofft and they work okay as long as I don’t overdo it. I have to be so very careful, but I am slowly building a fairly nice collection of shoes.

  2. Thank you, Allie, for acknowledging that being stylish does not require heels! The PTA (physical therapist assistant) and yoga teacher in me cringe whenever I see a woman tottering by in ‘fashionable’ heels. Sorry–I’ve got my little soap box here–Wearing heels all the time can cause permanent damage to your body. ( I work in a chronic pain clinic; I see the aftermath of a lifetime of wearing heels. It’s not pretty and I feel so bad for these women as I educate them on how to alleviate the pain and re-balance their posture. We surely age and our bodies aren’t the same as the years go by, but for these women, they have to deal with pain that should never have occurred. For your future health–minimize the time in heels! I refuse to ever wear them at all. And I have never had foot problems–I do that simply because I value my body more than I value looking fashionable. OK, I’m hopping off my soap box! I just think everyone should be educated on the consequences of this fashion choice so they can make an informed decision about what they wear. It’s not the same as deciding between 2 different skirt lengths! This is a health issue.

      1. I have a son that walks on his toes pret much 100% of the time. So I was just curious about casts, surgery, or just letting it be.

        1. Do keep in mind all this went down for me in the ’80s so there is likely better options now. But I went to many a podiatrist during my childhood who had me in special orthotics to stop pronation which they felt would also prevent me from walking on my toes, did physical therapy, and had me do special exercises before bed. We did go to Children’s Hospital to discuss surgery and casts but I downright refused as I would be in a wheelchair for six months and as an elementary school child that sounded like a death sentence. Now at 37 I do still walk on my toes from time to time, especially when I am tired. However, hardly anyone has noticed my toewalking since I hit maybe high school. It didn’t affect my ability to play sports, hasn’t hindered me in any way except for cosmetic reasons. Due to all the toe walking I have a very fat padded ball of my foot, and very padded toes. This makes shoe shopping a bit difficult, mainly in regard to heels and dress shoes. I don’t have much of a curve at my Achilles’s tendon, which makes slingbacks and those elastic-edged flats unwearable. I have very thick ankles, shins, and muscular calves, which makes boots near-impossible and I can’t get most skinny jeans and many leggings up over my knees. Hope that helps!

  3. In the last paragraph, I think you mean exacerbate, not exasperate, although my feet definitely get exasperated by uncomfortable shoes. 🙂

  4. My feet grew 1/2 a sized too during my pregnancy. I wore heels till the day I gave birth. They were really a bother for me (just had to buy 1/2 size bigger). My son is now 4 and I am now back to my normal feet size.

    I remember 2 weeks before my due date, we went to a black tie affair and I insisted on wearing a pair of beautiful heels with ankle straps. I could not for the life strap them together and had to have my husband put the ankle straps on for me.


  5. I am really excited to read that heels aren’t required to be stylish! I once worked a retail job that required me to travel to up to 20 stores a week, and I was required to wear heels. At the time, I was relatively young (24) and thought heels = style. So I invested in quality shoes – for me – spending about $75 per pair. I bought Naturalizers and Aerosoles in particular. I spent up to 9 hours a day either driving my car or on my feet.
    These were comfortable shoes. I was comfortable wearing them, driving in them, walking around in them. BUT! At the end of my first year, my pinkie toes were permanently deformed and the nail on those toes still grows in funny 7 years later. After about a year of wearing these nice, quality shoes that were so very comfortable, they started becoming uncomfortable to the point that I would drive barefoot just to get them off my feet. I also stated having issues with excruciating heel pain (like I was being stabbed in the heel) and arch pain. I ended up seeing a doctor who said this sort of thing was common, even in “comfortable” heels. I ended up giving up heels then and there (only exceptions are weddings or fancy parties). I have been wearing cute, comfortable, quality flats for about 6 years now and I have no more issues with my toes or feet. But I do feel like there is so much pressure on women to wear heels, and it’s just silly. And my pinkie toes are still all gnarled and funny-looking, which makes it seem even sillier to me. If you can rock them, rock them. If not, spend that money on some cute flats and call it a day.

  6. I am a grad student so most of my life is spent in worn out sneakers, but this summer I worked at an internship position in a “real” company so I invested in a pair of heels to go with my business pants. I really liked SoftSpots “Neima” — they are not too high (2.5 inch) and the sole is super comfy! I can wear them all day and still walk briskly to the cafeteria for lunch 😉

    I wish they would come in more colors (for my size foot, some of the fun colors were sold out). They might not work for every office, though, since they are open-toed.

  7. I totally agree with everything you said! I’d also add to try out different heel shapes, not just heights — for example, wedges, platforms, & any kind of slightly chunkier heel can be more supportive than stilettos or kitten heels of the same height, due to the width. That stability can make the shoes easier to walk & stand in for longer periods of time.

    I’ll also recommend Clarks & Aerosoles as being very comfortable brands. Neither have super trendy styles, but you can find classic office-appropriate pumps, plus a few really pretty styles each season. They’ve been upping their game in the past few years.

  8. I just love your blog and today’s subject choice is PERFECT for me! I haven’t worn heels in years and always wondered how women transition back after wearing flats for so long. I’m going to give it one more try. Thanks, Allie!

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