Reader Question: How to Wear Heels
February 25, 2010, 6:30 am
Filed under: shoes


I feel a little presumptuous writing this since I don’t actually consider myself an expert on the subject or anything, but an awful lot of readers have commented on how often I wear heels and asked how I am able to handle them. Actually, I too felt that way about other women for a long time.  Being fairly tall, many people around me actively discouraged me from wearing high shoes, so I didn’t have a lot of experience with them and I thought I would never really be able to master them. However a while back I stumbled onto the lovely (but now “out of print”) blog A Serious Job is No Excuse when watching The CW reality series Stylista. (Author Johanna was one of the contestants and the eventual winner.  And now she works at Elle!  Go Johanna!).  I greedily trawled through all the back archives, soaking up all the wisdom and wit, and while doing so, I noticed how Johanna would often write about her penchant for sky-high heels, or expound upon the benefits of a perfect pair of pumps in every professional wardrobe, and casually mention her adeptness at walking long distances in stilettos, even donning them for her (many block!) commute to her office.  I goggled; most heels seemed to make my feet want to cry, even for a few short hours, even when stationary.  She suggested practicing and working one’s way up; I was still dubious.  But it gave me a lot of inspiration and the confidence that incorporating heels in my everyday life could be done.

So one of my new year’s resolutions for 2009 became to try and learn and wear high heels.  Frivolous, I know, but all those heels in my closet were just collecting dust, and I needed to do something about it.   And wouldn’t you know it, within a month or two, I was happily wearing 3″ pumps on my walk to work every day.  I stopped eying the heels in the back of my closet in fear, and instead started looking forward to working them into my outfits.  Here are 10 tricks and tips that helped me through this transition:

BodyGlide Anti-Chafe Balm – $8.99

1. Blister Block.  I carry a stick of this stuff in my purse.  I mentioned it in one of my posts a few days back, but I think a lot of people had specific questions about what it actually was.  You can find many different brands of blister block at the drugstore, but they’re all essentially just a slightly less greasy version of petroleum jelly.  Blisters are caused by one main thing: friction — i.e. the leather of your shoe rubbing against your skin.  However, when you coat the areas of your foot where rubbing would occur (for me, usually the backs of my heels and the tops of my toes) before you slip your shoes on, the leather will glide instead of rub against your skin. No friction, no blisters!  Usually you just need this stuff for shoes that are on the newer side or that get only rarely worn; properly broken in shoes will have softened leather that’s molded to your foot and most likely won’t cause blisters.

Rite Aid Super Moleskin – $3.29

2. Another alternative to blister block is moleskin.  It’s available for pretty cheap at most drugstores and can really work wonders.  If there are specific areas of your shoes that have really stiff leather that rubs or digs into your skin, just cut off a swatch of this stuff and affix to the aggravating area of the shoe.  Voila — instant padding and no more rubbing.  I actually tend to use this a lot on new ballet flats, which always seem to dig into the tops of my feet otherwise.

3. Buy shoes that fit.  That may seem obvious, but I have been guilty once or twice of squeezing my foot into the nearest available size if the shoe was really SO pretty that I had to have it.  Sometimes I’d buy a pair online and the fit wasn’t too great but I was too lazy to return it, so I tried to tough it out.  Oh lord, it is so not worth the agony your feet will go through, I promise.  So, whenever possible, try shoes on in person, and if you can’t do so, do try to get an idea of the fit from online reviews (from Zappos, Endless, blogs, forums…), know the size conversions from country to country and be familiar with the sizing differences between brands and countries (for instance, US 8 is generally equal to a European 38, a French 38 generally runs a little smaller, etc.)  I once made the mistake of splurging on an (unreturnable) pair of Christian Louboutins peep toes in a size 41, not knowing that a Christian Louboutin 41 is a US 10 and not an 11 (usually anyway, the sizing is crazily inconsistent across styles) – I tried my best to walk in them but my feet practically rebelled.

Foot Petals Stiletto Stylist Set - $50

4.  Take advantage of insoles, cushions, pads and inserts. On the other hand, if you have a pair of shoes that is just *slightly* too big for you, there are a plethora of products out there that will help adjust your feet to fit perfectly.  Heel grips close that gap in the back of a just-barely-too-large pair of heels and foot pads will stop your feet from slipping forward.  Too big shoes may not seem as bad as too small shoes cramming your toes, but gaps and slippage can make it harder to walk and are also a leading cause of blisters.  In addition, Foot Petals — and their many generic knockoffs — make amazing feet cushions that can be lifesavers for shoes that don’t come with enough padding (and sometimes with 4+” heels there is NEVER enough padding).  If you feel like your foot is getting a lot of stress or pressure at a specific point, a strategically placed cushion — at the ball of your foot, on the arch, on the heel or covering the whole sole — can work wonders and prevent blisters and that awful achey/burny feeling.

5. Invest in nice shoes.  Not always (and only up to a point), but generally shoes that have a higher cost do actually use nicer materials and have better worksmanship; they use real leather, they have a nicer fit, and there is actual padding under the sole.  I’m not saying you always have to break out the Manolos (in fact my most expensive shoes are a pair of Thomas Wylde boots that hurt like hell), but be aware that when you buy discount shoes from Payless, Target, Go Jane, Forever 21, etc. their soles are padded with nothing more than cardboard, and the synthetics they use can be stiff and unforgiving (not to mention sweat-inducing), making them potentially quite achey.  Resultingly, in the end, the cost per wear for the fast-fashiony shoes can sometimes end up being higher than the  for the fancy-pantsy ones.  I have a pair of black Cole Haan Pumps (w/ the Nike Air technology that makes them feel like clouds!) that cost $300.  I adore them and I’ve probably worn them at least 150 times in the last 3 years.  I also bought a pair of completely adorable red bow-topped peep toes from Target around the same time for $19.  I wore them once (my feet still have the scars). That’s an almost ten times higher cost per wear!


Aerosoles Benefit Peeptoes – $89

6. Consider comfort brands and styles.  Aerosoles, EasySpirit, Naturalizer…these aren’t exactly brand names that usually conjure up fashion in my mind (I usually imagine something closer to sensible orthopedics), but their shoes, even their heels, are SO padded and comfortable, and amazingly, they are making super super cute shoes these days at really affordable prices.   Check the above uber-cute Benefit Peeptoes or the Roleplay Mary Janes (for $40!) from Aerosoles, the Easy Spirit Amira, or the Naturalizer Bohemia.  Sofft (maker of my beloved Fleur Pumps), Born and Clarks are other comfort brands that make really pretty shoes.  (Less affordable is the above-mentioned Cole Haan with Nike Air line of shoes, but they really are fantastic comfortwise.)  And in general, consider heels with a nice sturdy block heel that will support your weight much better than a pair of shaky pencil heels.  Think of these as “intermediate” shoes that will get you used to walking with the height of heels without dealing with most of the other annoying comfort issues, allowing you to work your way up to less sensible designer stilletos eventually :)


Women’s Shoe Stretcher - $19.99

7. Give your shoes a chance until they are broken in.  New shoes are rarely all that comfortable, the leather needs to soften up and adjust to your feet.  Some of my very favorite and most comfortable heels were nightmares the first time I wore them (not that I was smart enough to use blister block or moleskin at the time), and I was this close to throwing them out, but one day, after a couple wears, they just…stopped hurting.  Started being pretty damn comfortable in fact.  They had reached that magic broken in state.

If you want to expedite the breaking-in process, you can wear your heels with a pair of thick socks around the house, spray shoe stretching spray inside your shoes (you can buy this from a lot of places online, or you could just use rubbing alcohol, they are pretty much equivalent) and/or stick a shoe stretcher in there to break the shoes much faster (or a cobbler can also do the stretching for you).  Shoe stretching can also help you out with shoes that are just a little too small and pinchy on you, though I wouldn’t rely on it.

8. Practice.  A Lot. Walk around in your (carpeted) living room while wearing your pumps for a while (I used to do this while watching TV), and the correct balance and right heel-wearing gait will come to you in enough time.  I found aiming for a heel-to-toe stride was most comfortable and quick for me, but it may be different for other people.  Just try to get to the point where you make a “click” instead of a a “tromp,” and can avoid the dreaded sound of a heel scrape :)


Rollasole Ballet Flats – $9.95

9. Keep emergency supplies around.  Sometimes, a pair of new heels (or even your trusty old ones) doesn’t work out, and after a few hours of valiant effort, it’s time to admit defeat.  I keep a back up supply of ballet flats in my car, in my desk at work, and, if the occasion seems precarious and room allows, in my purse.  I also have an emergency band-aid or two in my side-pocket to put on any nascent blisters that might arise before they can start getting worse.

10. Treat your feet nice. When your feet are really tired and achey at the end of a hard day or bad heels wearing experience, pamper them with a nice soak in hot water and a mini-pedicure, combating any aches and/or callouses that may have arisen.  If you still ache, try a device like the Yogatoes, that will stretch out your muscles, relieving your feet and combating a lot of damage that heels can otherwise do to your feet.  Furthermore, try not to get in a heel-wearing rut.  I usually alternate wearing heels or flats, and even when I don’t, I never wear the same pair of heels twice.  Feet do not like being conformed into the same shape too repetitively, so be sure to give them a break.

Well that’s it!  Let me know if you guys have any specific questions, thoughts or advice of your own.  I admit I still don’t love wearing heels that are 4″ or taller or platform shoes, but for the most part, wearing heels is not something I have to fret about anymore, and they’ve really become a daily component in my wardrobe. Unfortunately, I was so excited at my newfound ability that I went on somewhat of a heel-buying bender last year, but at least my closet is the prettier for it, even if it so overflowing that my door no longer properly shuts ;)

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53 Comments so far
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I would like to add- wear a different pair of heels/diff height each day! Wearing the same pair will hurt after a while, whereas changing up the shoe gives your foot a bit more rest. 3 1/2″ one day, 1 1/2″ the next day, 2″ the next day, etc. I use this rule and it helps a LOT.

Comment by Meli

Yes, this is so true, and I what I was ineptly trying to say when I said to rotate your heels! Thanks for putting it into much better terms for me. My feet definitely get cranky when they’ve been put at the same angle/position for more than one day at a time!

Comment by goldenmeans

These are all fantastic tips! I love heels and I wear them frequently, but I am fairly tall as well and sometimes I feel self-conscious towering over everyone. Being COMFORTABLE eases that concern a LOT though!

Comment by ady

Aw, that’s definitely what I felt too for a long time. People (even my close friends) come up to me sometimes and say “Oh my god you are SO TALL in those” but I’ve come to realize it’s not meant as a criticism, they’re just feeling short ;) (Well at least my friends…) And so when anyone says that to me I just smile back and don’t think anything of it anymore :)

Comment by goldenmeans

Great tips, thanks, Anjali! I must invest in some blister block and foot petals, stat! I often have to wear heels to trade shows and standing on essentially concrete all day KILLS my feet.

Comment by Lisa

Ah, I am no fan of concrete floors either! I work in a converted industrial space so there are concrete floors all over the place and if my feet have been hurting I always avoid them and try to find some type of carpeted path.

Comment by goldenmeans

Great post Anjali. I use a Blister Block, but it is a different brand than the one you posted. Also, I have problems with the cheaper shoes made out of synthetics. Those are the shoes that make my feet bleed, etc. I did use foot petals once, but they didn’t do much for me. xo


I think all the brands of blister block are pretty much equivalent anyway, but I’ve been thinking of switching to the (slightly overpriced) BandAid brand lately because the tube it comes in is so much smaller and more convenient! The one I have is the size of a deodorant stick and takes up way too much room in my purse ;) And yes, boo on synthetics!!

If Foot Petals don’t really work for you, have you tried the Dr. Scholl’s kind with the gel-cushions? They seem like they would be even cushier and I am curious about them myself….

Comment by goldenmeans

I love that you are tall and still wear heels! Everyone looks at me like I’m insane when I come strutting in wearing 3+ inch heels, but shoes really can make or break the outfit. These are all great tips (that I agree with 100%)!

Comment by Kathleen

It definitely took a lot of self-confidence building to get to that point, I was really self-conscious in tall heels before! People still make comments but usually in a positive way (Although I had some guy at the mall try to come and hit on me last week by saying, “Oh, I feel so short next to you!” Hrm, not a successful pickup line.) I still prefer short heels, but mostly because they are easier to walk in/more comfortable…but the prettiest heels are always the tallest ones, no? :)

Comment by goldenmeans

Awesome post! I agree with everything you said and have one tip of my own to add: find a brand that works for you. Everyone talks about how great the Nike Cole Haans are but they kill the balls of my feet and don’t conform to the arch of my foot very well. I’ve had much better luck with Coclico, Jimmy Choo, etc.

Comment by roxy

That’s a wonderful tip Roxy! I think the cut of different brands can suit different types of people/feet. For instance some people swear by Louboutins but I personally find his shoes hideously uncomfortable (even when they are my proper size ;) ). And lately, on the low end, but I have been loving Seychelles shoes!

Comment by goldenmeans

Yay, thanks for the tips! I’ve always admired your heels and you’re one of the reasons that I want to start incorporating heels into my wardrobe so badly. You always look stunning in them! I definitely will get some blister block and moleskin (I didn’t even know that stuff existed) and practice around the house so that my “tromp” will turn into a graceful “click.” Thanks again!!

Comment by amy kelinda

Awww, thank you Amy, you are too sweet!

Comment by goldenmeans

This post is really great. I have been going sort of nuts buying heels lately, but I just CANNOT walk in them. Probably because I’ve been wearing flats every day for years. Not to mention that I just came to the realization about a year ago that I am in fact an 8.5, not a 9 in shoes.

I want to be a real adult and wear heels! haha. So thanks a lot for posting this.

Comment by Christine

Aw, you’re very welcome Christine! I hope this post allows you to get some use out of your heels! I wore flats every day too and was somehow able to convert.

Comment by goldenmeans

Finally delurking! I love your blog and your sense of style and this post is a huge help! Thanks!! I’ve just started getting into heels and love wearing them. But, I hate the sound I make when I walk in them. Are there any tips to stop the clicking or do I just have to practice a lot??

Comment by couchpapaya

Thank you for commenting! :) LOL, I kind of like the delicate rhythmic clicking sound heels make myself, but if you are not a fan, you can get your cobbler to replace the heel caps of your shoes with rubber ones.

Comment by goldenmeans

Great post! Thanks for all of the advice/information.

Comment by Kristin

:) Thank you. I hope it helped you out some!

Comment by goldenmeans

Thanks for the link to those Aerosoles! I had seen them before but they weren’t on sale so I passed.

Comfort shoes rock. I wore high heels every day in high school (dress code), and I thought nothing of running several blocks in them (to get to my bus on time) and in general I didn’t consider heels to be the torture that a lot of people do. But it wasn’t until this past fall that I actually got Naturalizers, and I couldn’t believe how comfy they were when I put them on! I have a few other pairs of heels I wear for long days, but overall I’m pretty much sold on getting comfort shoes for work days for the rest of my life. The non-comfort ones can come out at night :)

Comment by Kelly

Yeah aren’t comfort shoes fantastic? Sometimes other shoes seem like torture devices in comparison. I am dying over the cuteness of the Aerosoles Benefits and really want the red ones, but I don’t know how responsible it is of me when I own like 5 other pairs of red shoes. However, are any of them as comfy? I don’ think so! Sigh….maybe at sale/code time, like you :)

Comment by goldenmeans

Anjali, thank you so much for posting this! I’ve always had trouble with heels – even with a pair of comfort heels (can’t remember if they are Sofft or Born). I actually wore them on Tuesday and my toes still hurt!

Comment by Lauren

Oh no! Yeah sometimes a brand, even a comfort shoe brand, won’t work out perfectly for everyone…I think you should find a brand/style/fit that works best for you :) And always do a carpet walking test to determine if shoes are *really* comfy for more than 5 minutes before you wear ‘em out!

Comment by goldenmeans

Lovely post! I’m a big fan of heels and used to wear them quite often (my hilly San Francisco commute has now made me a bit lazy on work days). I used most of this tips to get me into wear heels except for the expensive shoe part. As much as I was addicted to nice things in theory, I figured the quality difference wasn’t going to be too obvious after a certain point. I was definitely wrong! I only just got my first pair of super expensive heels and the quality difference is really astounding. Colour me converted!

Comment by Alissa

LOL, if I had to walk up San Francisco hills, you better believe I’d be wearing flats on my commute and switch into pretty shoes once I got to my office :) So I don’t think you are “lazy” at all! And yeah, pricey shoes can certainly be surprisingly nice! (Though definitely not always!)

Comment by goldenmeans

This is a great list of tips! :) I unforunately have too many foot issues to wear heels for more than a few hours, but even I have managed to find a handful of pairs that work for me! I do covet your collection though, especially all the color.

Comment by e.

Aw, thanks e. And I’m glad you have some pretty heels for yourself even with your foot issues. Every girl deserves to prance around in heels once in a while :)

Comment by goldenmeans

I’m starting to wear heels more often. The biggest problem I have is not being able to go down stairs! It takes me forever! Any tips?!

Comment by amber

Haha, I hate stairs too! I haven’t quite mastered them yet, but I think the general idea is to grip the railing, angle your feet a little towards the hand rail and put your whole foot on the step. I still kind of clomp when I do this, but I think the key is, again, to practice.

Comment by goldenmeans

Nice article and I started wearing heels again somewhat consistently a year or so ago. 3-4″ are basically no problem. Over 4″ is a problem, I won’t lie :-) You hit all the things I’d mention, especially, the Foot Petals line, the purchase of better quality shoes with a leather sole and insole and also Insolia makes a nice insert that spreads the weight of your foot. Keep up the good work!

Comment by Bronzi

Thank you Bronzi. Ha, I am not super happy with over 4″ either, I can only wear them for a little while, I don’t know how some girls do it. And thank you for the Insolia recommendation — I had never heard of them, but now plan to check them out!

Comment by goldenmeans

Thank you for posting this! I’m about 5’7″ or a little over, and taller than all of my friends. I never wore heels because I’ve always been taller than my friends but I want to wear heels more – but I don’t know how!
This was very helpful to me! Thank you :)

Comment by N

You’re welcome N! Ha, I am taller than all my friends (and boyfriends!) when I wear heels, but they’ve gotten used to it ;)

Comment by goldenmeans

Thanks for this post.

My questions is regarding high boots. I recently bought 2 pairs. I am a size 7 usually (left foot seems to bigger (??) than the right! HA!

Of these 2 new pairs, one is size 8 (left foot fits comfortably with wiggle room in the toe part, right foot could use some stuffing in front of the toes). Have you (or any other readers of this post) used any kind of Dr.Scholl padding or similar kind so that I can use those to enjoy this size 8 pair comfortably?

The 2nd pair is 6.5, and left foot is a bit tight, so it looks like i need to take it to the cobbler to stretch it. Anything else you guys recommend?

Many thanks!

Comment by F

If I were you I’d try heel grips at the heels or lambswool at the toes, or a combination of the two. You can get lambswool in a ballet supply store.

Comment by Kelly

Thank you so much! I will get those heel grips for the heels and lambswool for the toes and try them out, separately or in combo. Never even heard of the use of lambswool for this! Thanks.

Comment by F

It’s crazy, but almost all people have one foot that is slightly bigger than the other…my right foot is a tad bit bigger than my left, and for some reason this is only an issue for me with boots! Anyhow, just saying that I feel your pain a little bit. For the 8′s, I second Kelly’s suggestion of lambswool, or even just wearing an extra thick sock on your right foot. The 6.5 I would definitely just get stretched by a cobbler (they hopefully have a boot stretcher that will reach down the shaft).

In the future though, you might want to consider buying shoes from Nordstrom. They have amazing customer service in general, and for ladies with odd sized feet, they will sell you a pair of shoes that matches both of your feet (e.g. one 7 for your right, an 8 for your left). At no extra charge! I don’t know of any other stores that do that, but I think it’s kind of awesome!

Comment by goldenmeans

Never tried out 2 different sizes! Will go check out tall boots from Nordstroms this weekend.

I do have thick woolen socks that I will try out, and then shop for Kelly’s recos too. Thank you for the tips again.!

Comment by F

Whoa holy great post, Anjali. Thanks for posting this!

Comment by Chloe

:) Aw, thank you Chloe!!

Comment by goldenmeans

Thanks for the tips, lady! Being more of a high heel wearer is constantly one of my goals, but being a student and working retail seem to keep getting in the way. I’m ready to have a job/lifestyle that allows me the luxury of nice shoes!

Comment by Jinah

Yeah, if I had to walk across campus and then stay on my feet all day on a job, I don’t know if I could actually wear heels all day either. Well, maybe only Aerosoles or something :)

Comment by goldenmeans

Fantastic info. I added a link to this post to the front page of my blog ;-)

Comment by GigiofCA

I have tried all of these tips countless times, but my feet STILL pain after an hour or two of wearing heels. Sigh, I wish there was something I could do about it! I’ve come to the conclusion that I just have sensitive feet :(

Comment by Leia

Oh no Leia, I’m sorry! If even after practicing for a while and wearing comfort shoes like Sofft and Aerosoles that have a lot of cushioning, your feet still hurt a lot, it’s possible that it really wasn’t meant to be!

Comment by goldenmeans

Hey, late comment but I know this thread is going to turn up for people. I recently got a couple of pairs of Camper high heels that are awesome- on the sole is actually written ‘heels for beginners’- you can run and jump and play (:P) and I`ve since been much more adept with other heels!

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