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Tales from a Shoe Addict: The Four-One-One on Shoes

Another Cali masterclass!

By Cali

For our younger readers, 411 was the number dialed for get a phone service called “Information”. Now you just Google it…

I confess, I’m a shoe addict. Didn’t use to be. I hated shoes when I was a young and hated shoe shopping even more. The reason – shoes never fitted my feet.

In 2011, after yet another ankle reconstruction, I searched for shoes that fit my feet. I have strange feet, a thick toe box, massive arch, and skinny heel; my podiatrist tells me that less than 1% have feet like mine. I could just barely get my toe box into men’s 9.5 EEE shoes, then had about ½ inch gap on each size of my heel and a ½ inch gap in front. I determined these gaps were a contributing factor to my many reconstructive surgeries. I searched the internet for “thick toe box/narrow heel shoes” and the only shoes that Google came up with were women’s. I tested this theory with a pair of cheap women’s running shoes, and the regular women’s size 10 fitted better than any men’s version had ever before. I switched to women’s shoes that day. And haven’t had ankle problems since.

Now that I found shoes that fit, shoe shopping was fun. I got several pairs of booties with 1.5- 3-inch heels and more runners.

In 2015, I was forced to raise both my heels 4 inches to heal a severe leg injury. Since you can’t wear two plastic booties, I told my doctor I was going to try high heels. After 5 months in 4- inch heels, I tried to go back to flats (or 1-inch heels) and my hip pain (from a previous injury) returned in one week. I have been in high heels ever since.

I’ve learned a lot about shoes and shoe shopping, and I want to transfer that knowledge to you.

Basics of Shoe Shopping

Many women’s shoes, unlike men’s, come in and sell out fast, never to be seen again. If I find something that fits great, I will sometimes buy a second pair – maybe in another color.


This is THE most important feature. I bought my first pair of 4-inch heels from a clearance rack at DSW. A woman shopping in the same size range saw me trying on heels and told me this very important principle of shoe shopping, “Life’s too short for shoes that hurt.” I live by this. I put my shoes on in the morning and go off to work. I wear them for 6, 8, 12 or even 16 hours straight. I can’t afford heels that hurt.

Women ask me all the time “don’t your feet hurt?” And I usually respond with “I only buy shoes that don’t hurt.” A shoe maybe very cute, even gorgeous, but if it doesn’t fit, the “cuteness” doesn’t matter. Most women buy heels based on looks and don’t worry that they don’t fit right. It’s no wonder women say they can’t wear heels when fit is at best a secondary factor. It’s hard to be confident when your feet hurt. In many posts here in Kandis’ Land, were the author say their feet hurt after 2 or 3 hours in heels.

If they are cute BUT hurt when you try them on, don’t buy them. If they hurt after an hour, two hours, take them back. I’m not saying, “don’t buy cute shoes”, rather, “only buy cute heels that fit!”


There are many tables on the internet that will convert sizes, men-to-women, USA-to-EU, etc. In the U.S. the rule of thumb is your women’s size = men’s size + 2. But size varies even within the same brand, some

makers are known for narrow shoes, some foe wide shoes. While most of my heels are size 10, I have a few that are size 11. Toe shape – pointed, round, almond, straight – plays a role here as well.

If the shoes are leather or suede you may be able to stretch them a bit, but many man-made materials do not stretch. See Tools below.

I consider myself very lucky because I wear a size 10, and that’s considered a normal women’s size. Therefore, I can shop anywhere, but it doesn’t mean I can wear every style of shoe. There are still some styles that will never fit my feet. I feel for those with larger feet.


I use gel pads in almost all my heels. I was given my first couple of pairs and have purchase the rest. They perform two functions; they make it softer on your toe pads and they help to keep your foot from sliding down and stuffing your toes.

The other thing I keep around are blister pads. Sometimes new shoes need to be broken in and blister pads come in handy.


I have two tools that I use. High-heel shoe stretchers, shoe stretchers that are made for high heels. And a (Leather) Hole punch. Very useful in adding extra holes to straps or enlarging existing holes. I sometimes add two or three holes to a toe strap.

Although it’s not a “tool”, inserts for keeping your boots from folding over is very important. I keep the inserts that come with my new boots and store my boots with them standing up. I make insert from cardboard for my tall boots that don’t have inserts. My boots are expensive investments that I plan on keeping for many years. Store in a cool DRY place and they will last for years.

Shop Amazon’s Handbags to go with your shoes!

Learn to Walk

I was lucky, it took me only minutes to find my balance and be able to stand, walk, and lecture for hours in 4+ inch heels. But most will need more time to get comfortable walking in heels. Take your time. Don’t start with stilettoes, get comfortable in block heels or wedges. After mastering walking in-doors it’s time to take it outdoors. Walking outdoors is very different. Surfaces are not always flat, some tilt to one side, are uneven or are littered with debris. Cracks are everywhere, in sidewalks, wooden decks, at elevators openings and stilettoes are magically attracted to these cracks. (BTW – stilettoes are great for aerating your lawn.) Walking down a steep driveway is EXTREMELY hard. I’ve been known to have to hold on to my girlfriend (while she laughs) to make it down some driveways.

Above all, you need to be confident walking in your heels. It’s hard to enjoy your heels if your feet hurt with every step. If you are fumbling around, unsure in your walking you will draw unnecessary attention to yourself. And be careful on stairs, it’s very easy to catch a heel on a step so always hold the handrail.

Above all, enjoy your heels.


9 Responses

  1. Hi Cali:

    This is Gigi with the size 15½ feet from Massachusetts getting back to YOU!

    I still have the two pairs of high heels I acquired thanks to you from Pleaser (via a concern way out west in Southern Cal). Of the two, the black Mary Jane type fit like a glove and I wore them all day last Sunday. I felt good enough to dance in them (and that says a lot because I sometimes have trouble just trying to walk at all). The enjoyment was magnified when they were matched with a great looking set of layered city beige pantyhose, which drew eyes to my legs here and there through the day–I could tell that much!

    The other pair is a 15 Patent leather black pair which work OK, but I had to do field adjustments. I took several old pairs of woolen ankle socks and cut them in various-sized strips to stuff the pointy toes, until my feet would stop riding frontwards from the 2-inch heels and were snug at the back of my heels without ANY discomfort. During my hours wearing them (all day Sundays) I will periodically pull both my feet out to make sure there is no sign of “hosiery scuffing” (i.e. runs) as we go, which means they’re fitting as they should.

    My other problem with these is my feet seem to be unequal in size, so where the right side works fine (but needs added protection for two tender biggest toes), the left appears to be slightly smaller. If I am on any kind of a mushy floor I note the left heel will “roll” which means that hoof is then “in the bucket” if you will (a wee small for the whole shoe). It all depends on wear I’m walking and its environment.

    What I learned at our church is there is deep, soft carpeting in the trip between vehicle and my best seat in the sanctuary, including one short elevator ride (I am HP). I started early (by end of May) keeping my patent heels in my purse until I actually get to my seat (usually a good 20 minutes before service) and change to the heels there, then the reverse when things conclude. I take my sweet time leaving the church back to my car after that. Then after back home the patent heels are put back on my feet for the rest of the day, more or less.

    The other summer footwear for my 2023 collection now includes two pairs of Mens 14/Womens 16 Crocs (one khaki, the other “palm” a greenish blue) I got from Zappo’s and three pairs of colored Birkenstock sandals (red, blue and black international size 46) from DSW. I tend to use the sandals as slippers around the house but NEVER for driving. That’s where the Crocs come in, as they have a heel band which prevents my feet from sipping off the gas or brake pedals.

    Last note I try to keep socks on for the Crocs (“Pride” striped anklets from Bombas) and virtually always go barefooted for the sandals. This the first time I have had such footwear in about 40+ years after a lot of “blood and sweat” to get my toes to behave, thanks to not one but two caring podiatrists, tons of skin balm (Mupirocin) and medicated skin moisturizing lotion.

    They don’t look special on the surface right now, but after my first pedicure these are two very expensive bare feet at this juncture, adorned in red nail polish (well, at least 8 of the ten toes I have because I had to have the entire nails on both big toes removed years ago).

    As always, thanks forever for you and Kandi!

    Love, Gigi

    PS: She who just got her new driving license and has now legally become an “F”!!

    1. Hi Gigi,
      I’m glad you found shoes that fit. Pleaser is known for larger sizes. Another large size heel maker is Onlymaker.
      As you found out, walking on plush/heavely added carpet can be a challenge, so be very careful.
      Pointed shoes also tend to be narrower than others. I look for round or almond shaped toes for most of my shoes, but I have a weak spot for Jessica Simpson stilettos and those tend to be on the pointed side.

  2. Cali, great advice, thanks.

    I would say that there’s something about high heels that makes me go weak at the knees but sadly that’s true in a literal sense these says as well as the metaphoric sense! And I too discovered the perils of walking down a steep driveway in 4” heels the first time I went out but have been a lot more sensible since!

    The importance of a good fit can’t be overstated though. I have a ruined toenail from just walking around the house in a pair of ill fitting heels which resulted in a blister beneath the nail. Sometimes we just have to suffer for our art!

    1. Amanda J.,
      I hope you had a friend to hold on to on that steep driveway. And I hope that friend didn’t laugh at you all the way down, like my friend did and continues to remind me.

      I can’t over emphasize how important it is to get shoes that fit. I my infant heel adventures I got a few pairs that I force myself to get, heels I always wanted, like calf-high booths and CFM’s. But I can’t wear them for hours on end, so I don’t wear them. Good shoes can be an expensive investment and you don’t want to waste money on something that hurts you.

  3. Thanks Cali, An excellent informative and useful article. However, I cannot get the old saying out of my head “If the shoe fits, it must be ugly.” 🙂

    1. Daniele
      That statement has led to women not wear heels. Many women have told me that they hurt their feet in “cute” but ill fitting heels and can’t wear heels now. Don’t be one of those
      Swap that saying with the one “Life’s too short for shoes that hurt.” I don’t buy ugly shoes, there are plenty of shoes that are ugly and plenty that aren’t.

  4. Cali,
    It’s good to read that you sorted your feet problems out , long term we shouldn’t ignore problems with feet as we may suffer for the rest of our lives .
    I agree sizing is a minefield the only real solution is to shop in retail stores and try them on , I will add over the years I’ve had the most fun with SAs and customers . I never think twice about buying them from charity shops , the point being someone else has worn them in , I’ve found the most comfortable shoes from charity shops . Your sizing guide is only a rough idea , I shopped using the old guide line of buying a women’s shoe one size larger than my usual male ones . I soon discovered that women’s feet have grown and caught up with male sizing so I find my UK male size 8 is equivalent to a female size 8 . The one to watch are the imports from the Far East where they can be undersized by more than two sizes , I no longer buy from those suppliers because I’ve had to return every pair .
    Sadly less women wear higher heels so the choices have disappeared off the shelves , most of my shoes now are heeled wedges which prove to be a good compromise both in style and comfortable fit . Annoyingly the shoe I can’t often wear are peeptoe shoes because of arthritis in my big toes , I love them when my toes have fresh varnish on but soon pay the price with sore and blistered toes .
    Thats a good tip about keeping boots in good condition and I have found synthetics do stretch if you apply a little heet from the kettle or hair dryer while applying the shoe stretcher but don’t overdo it .

    1. Teresa,
      Thank-you Teresa. We all have different feet and mine are really strange. My podiatrist puts my arches in the top 0.5% of all arches she has ever seen and recommends at least a 2.5-inch heel to absorb my arches. Try some blister tape and tape your big toe in place, it might help with your arthritis. I tape one of my small toes from underneath to keep it from poking out of my gladiator sandals.
      I agree sizing is a minefield. For example, take Jessica Simpson, there were 4 versions of the same basic stiletto with only slight variation in where the neck was. I fitted into one in a size 10, one in a size 11, and couldn’t fit the other two in either size.
      I have many sandal wedges and they are some of the easiest to walk in. Added advantage, these show off my pedicures.
      Thru trial-and-ever I have narrow down the type of shoes to even consider. Pumps are completely out, their vamps cut into my toe tendons. I look for shoes with toe straps that I can adjust with my hole punch. Lace-ups are very good candidates. And I only look for boots with full zippers.
      When you’re a male and walk into a shoe store with 4-inch heels on, the SA see you as a serious customer and you will get better service.

  5. Cali,
    The problem I’m finding is the influence of Euro sizing , a genuine UK size 8 should be a eu42 but often I find they are marked as 41 or 41.5 which is a UK size 7 or 7.5 . I believe a UK size 8 is equivalent to a US size 10 which is usually the largest size stocked in most restail outlets .
    I hope you don’t mind me repeating a story of buying a pair of knee high boots in store . Back in the days when I shopped in drab I ventured into a large shoe store , I had taken the trouble to search the store online so I went armed with a suitable list of styles . Top of most people’s list is usually a pair of black patent , heeled court shoe ( pumps in the US ) . I’d already chosen a suitable pair when a lovely sales lady offered to help . On my list was a choice of boots , I’d never worn them before so really wanted to try some out . She went away and returned with the selection , she zipped me in and then told me to stand up and try them out as I did so we both became aware of a male customer staring at us with his jaw on the floor ! She looked back and me and we both began to giggle , that really broke the ice and she went onto tease me into buying some lovely shoes from the sales rack . Sadly like many retail stores it closed down and I never saw the SA again but I still have all the shoes , some I still wear but I keep them all because of the memories they hold .
    A second story again while in drab in a large department store . I needed some heeled party shoes , I couldn’t find any so I asked a sales lady for help , she then asked what size and how tall was the lady in question ( as she assumed I was shopping for my wife ) , I replied , ” You’re standing next to her !” With that she gave me a dig in my ribs with her elbow and grasped my hand to find some shoes .

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