Wearing High Heels Comfortably

Some of My Weekend Shoes

Most people notice that I wear tall heels.  At 5′ 3″ I feel like a kid looking up at all of the full-size people in my life (many of whom are younger than me).  I prefer at least a 4″ heel to put me more at eye level.  Some people are quick to comment on how I am “messing up” my feet over time.  Whether they are correct remains to be seen, but this has been my way for the past 15 years and so far I’m not seeing any signs of damage.  I have a few ideas on what I might be doing right.

Not Too Tight!
I think the number one way to make heels comfortable is to make sure they are a good fit.  Tight shoes hurt.  I’ve had a few pairs that put my toes to sleep.  Pointy-toe shoes seem to frequently become trendy (even though aesthetically they are not my preference), but imagine how terribly they squeeze your toes.  Add the elevation to the squeezing and sure, it’s going to hurt!  A slightly rounded toe usually conforms more to the natural shape of your foot. 

Personally, it seems that most pumps that fit me comfortably tend to slip while I walk, so I stick with Mary Janes or ankle straps for the most part.  Problem solved!  I feel super cute and comfortable, and almost tall enough to pass for a grown-up.

Stretch Your Toes, Lots

My Favorite Work Shoes

Yes, wearing heels puts the foot in an unnatural position.  But exercise often does the same thing to our entire bodies.  Does that mean exercise it bad?  Surely not.  It just means we have to condition our bodies for the activity and give them a little extra care.  That means stretching.

I stretch my toes and ankles well each morning before donning my heels.  I usually take my shoes off during my work breaks, which leads to a bit more stretching.  In the evening when the shoes come off for the day, another good stretch, and often again before bed.  While I’m at it, I make sure to give my back, arms and neck a good one as well.  This is in addition to my normal exercise routine, which is usually two 15-minute workouts four days per week.

Stretching just makes me feel better all over, and my feet rarely hurt even though I wear heels 11 or more hours at least 6 days most weeks. 

Invest in Good Insoles
There are inserts available to pad whatever part of the shoe is uncomfortable: the whole sole, the ball of the foot, the heel…  I like the fabric-coated gel insoles.  I replace them as soon as they start to flatten out a bit so they remain effective at cushioning my little feet.

Wear a Wider Heel

My Best Club Shoes

Yes: Stilettos are sexy.  But they are much more difficult to walk in than even a slightly wider heel.  I think the amount of difficulty in walking directly affects the overall comfort of wearing the shoes.  All of that wobbling and trying to stay balanced is stressful on the feet!  Go for a heel that’s at least 3/8″ in diameter.  For the weekends, I prefer a 1″ wide heel since I do more walking than while sitting at a desk during the week.

Platforms = Shock Absorbers!
I can do a full day of walking and shopping as long as I have a platform.  Even 1/2″ makes a difference.  Shoes with no platform at all make the balls of my feel hurt terribly, even with good cushioning.  My theory is that the platform acts as a shock absorber.  Often the taller platforms (1″ or more) are partially hollow.  Even fully-filled platforms just have more material to dissipate the impact with each step.

I hope these tips help those of you who are addicted to HIGH heels as I am.  Now tell me what kind of shoes are your favorite, and how do you keep them comfortable?

PS:  Remember those adorable Pleaser shoes I mentioned in my previous post?  I couldn’t resist.  They shipped today.  🙂

Images in this post are from Pleaser USA.


  1. I'm glad you liked it, Emilina! Will you be posting photos of your new shoes on your blog? I must see them! 🙂

  2. This is a really good post!! I, too wear HIGH heels most days! I am a little under 5'7" but I just like being taller! 🙂 I try to stretch often, and should pay more attention to my ankles. Good point! 🙂

  3. Emilina Sassperina

    Interesting! This is a great post. I never thought about stretching as a good way to prepare for wearing a great pair of heels. I just got a new pair of Jeffrey Campbells that I need to invest in a pair of insoles for!! 🙂

  4. Thanks, Krystle! I was hoping this blog would bring me into contact with other women who love some of the things I love. And I totally envy your height!! ;-D

  5. I love those heels! :))this post is really veeeeery good! I loved it *-*http://imnotmuggle.blogspot.com

  6. Platforms are the best. I don't even buy heels without platforms anymore! To me, the higher the heel the better and having platforms means the heels look ridiculously high. I have a pair of oxford platforms that look HUGE and I get some many compliments on them and how I manage to walk in them so gracefully. Well, if people knew that they actually almost feel like sneakers… ha! Most comfy shoes ever.

  7. That's awesome, Katie! Some of my platforms are like that too – not nearly as difficult to walk in as they look. But it feels nice when everyone is impressed with your skills, doesn't it! ;-D

  8. Your best club shoes are deliciously hot. Where do you usually order them?And here I had given up hope that there was a method to walking comfortably in heels. I'll take each tip and put it into practice~

  9. Sir Isaak, I have been ordering from Funky Pair lately, since Diva Treats mysteriously shut down their Web store a while back. 🙁 Diva Treats was a bit classier… But Funky Pair has been good to me so far

  10. just found your site and its great! I'm 5 foot 2 and often wear platforms to give myself a bit more height (doesnt work when all your taqller goth friends wear them too though *rolls eyes*)I like to try and find platforms that have good grippy soles (known as cleated by some cobblers) the type that are rubbery as they act as the best shock absorbers and give my smaller foot base more grip when i walk. I always go for thick heels (having weak ankles, i cant wear stillettos unless im wearing boots as the boot helps support the ankle)The best insoles i found for the balls of the my feet are called 'walking on a cloud' and i can only ever buy them at The Erotica show as they are sold at a shoe fetish stall! but dear gods, they make the tallest arch bearable.

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