How to Wear Heels (If You’re Used to Flats)

How to Start Wearing Heels | Corporette

2017 Update: We still stand by this advice on how to wear heels if you’re used to flats – links have also been updated.  

How can you wear heels, if you’re used to flats? Which are the best first heels to buy? How do you make the transition smoothly and effectively? Reader J wonders:

I have always been a flat, practical shoe kind of person with some style. For example, Merrill boots in the winter. But, I am really trying to increase my presence in the world and have read that shoes with more lift indicate more power, money, etc. How do I find higher shoes that won’t kill my feet after all these years of being practical? Advice appreciated!

I’m curious to hear what readers say here. We’ve talked about the best brands for comfortable heels, specific ways to make heels more comfy, and how to look professional in flats (even how to wear flats to court), but I have a few more thoughts on this:

a) Obviously, you don’t have to wear heels to be professional. Personally I think heels look better with most work-appropriate clothes (full-length trousers, pencil skirts, sheath dresses, etc), and I find them more comfortable, on average, than a lot of work-appropriate flats, but you don’t need them to be “professional.”

b) Ask yourself WHY you want to start wearing heels. For Reader J, she’s trying to “increase her presence” — I’m not sure heels are the best way to do that. Heels can make you taller, and I’ve always thought they made my legs look thinner, but I think it would be a long road (because I’m going to suggest you take it slow if you do start wearing heels) before you’d get to the kind of heels that are outfit-defining, personality, statement pieces. For example — Erin Callan was known for her 4″ Louboutins and similar heels — but I’m not sure a 1.5″ heel is really going to “say” that much more than a flat would. It’ll make you taller… it might make your legs look better than flats… but it isn’t going to increase your presence (unless you’re clomping down the hallway in them, in which case I’m not sure that’s a good thing).  Like I mention above, I think heels will enable you to wear more outfits that will in general look sleeker, and those will increase your presence — but I think more credit is going to the sleek wardrobe than the mere fact that you’re wearing heels.

c) If you decide to start wearing heels, start s-l-o-w-l-y.  Don’t try to go from wearing, say, flat boots (where obviously your foot and vamp are fully encased) to 4″ pumps — it isn’t going to end well.  Look for low heelsunder 2 inches! — at first, to get your feet used to some height.  (Both of the Hunt roundups linked have a lot of suggestions for specific low heels that are pretty much perennial styles, like the Stuart Weitzman Poco, also pictured at the top of this post (and on sale — was $298 now $158, available in sizes 4-12). After you master that heel height, consider going higher (I’d stay under 3.5″ for the next round, perhaps aided with platforms (no bigger than 1″; bonus if they’re hidden).  Personally I don’t think anyone needs to go higher than that unless you’re taking pictures or shooting film (I’ve found out the hard way that 3″ heels look fairly frumpy on film!) — for actual life, I think the 4″+ heels are for the true heel lovers out there.

A few other tips:

  • For my $.02, check out the comfortable mall stores first — places like Aerosoles, Easy Spirit, and Macy’s comfort boutique — and avoid other mall shoe stores that specialize in trends/affordability first (sometimes sacrificing comfort and quality).
  • Scratch your soles — if the soles aren’t rubber, make sure you wear them outside enough to get them scratched.  It’ll give you more traction.
  • Look for strappy pumps if you have trouble walking in traditional pumps.
  • Look for chunkier heels (possibly even wedge heels) — the skinnier the heel the harder it is to balance.
  • Go bare.  If you’re still in the breaking-in stage, consider wearing them sockless (no trouser socks, no pantyhose) — for some reason that always helps me.  (Of course, know your office — bare legs are not appropriate everywhere, particularly with skirts.)
  • Know your inserts.  Get to know the various inserts from Dr. Scholl’s and the like available to you.  For example, I have narrow heels so I always have to put in heel inserts.
  • commuting heels Find comfortable commuting shoes — possibly even commuting heels that are lower versions than your regular heels.  (I was obsessed with this picture in a recent Inc. magazine article on executive assistants — Barbara Corcoran switching into identical but lower heels after a talk show!) I always suggest a general six-block rule for heels:  Your heels should be comfortable enough to walk at least six blocks, but I’d be surprised if anyone (at least, anyone with their podiatrist’s blessing) is walking for miles in heels.

Readers, if you’ve worn flats for years and then transitioned to heels, how did you do it?  Readers who started wearing heels when you started your career, how did you start?  What are your best tips for wearing heels?  Readers who love flats, which are your favorite work-appropriate brands and styles — and what do you wear with them? 

Picture below via Stencil.


If you're used to flats, learning how to wear heels can seem like an insurmountable obstacle. These are our best tips on how to wear heels with grace.


  1. I am having a particularly rough go. I had a stressful weekend with my mother, while my kids tested every ounce of my patience, while my husband was away. He and I are not hitting each other’s “need” bullseyes, for lack of a better term–we’re each shooting, and just missing the mark entirely. Not for lack of trying.

    And a host of other things. What it all boils down to is that I am in a major funk, and sometimes I wish that I could just get out of my life. We don’t have the means to take a vacation, though that would be a nice respite–but of course, you return to the same old crap. I really don’t have the means even, to seek counseling at the frequency I probably should.

    I feel terrible saying all these things because I do really have it pretty good. But I just feel lost, alone, tired, exhausted, overwhelmed and dejected. I’m on meds for depression, and am currently in limbo with some dosing, so that is not helping at all. Not really looking for answers, just needed to get it out.

    • mama of 2 :

      I’m so sorry. The whole family-kids-work-household thing can be so hard and I’ve definitely had moments where I’m in a funk. Can you jettison anything? Is there a work project, a kid activity, a social engagement, a family commitment, or anything that you can just take off your plate? Can you get outside for a day this weekend and just soak in some vitamin D and a change from the routine? I wish you luck.

    • Senior Attorney :

      Aw! Big hugs to you! Kids and moms and traveling husbands can be tough!

      And let me urge you to get that counseling even if it puts a squeeze on the budget. It’ll be money well spent!

    • Blonde Lawyer :

      Regarding you and your husband not hitting each other’s bulls eyes. Have you read the Five Love Languages book? Was very eye opening for me.

      Do you have the ability to swap babysitting w/ another mom to get some time alone now and then? When I can’t take a vacation, a low end spa treatment can snap me out of a funk. If I don’t have time or can’t afford a 90 minute massage I’ll try to get a quick 30 minute/$30 one. If you are seeking peace and quiet could you use a free hour to go to a bookstore, a library, museum or even a church? This is super bizarre but I love wondering around Staples. It is usually very quiet in there and I’m a huge geek and love all of the cool office supplies I could buy. Try to just find a tiny little thing you do just for you each day.

      The other day I bought a $1 daisy and have it in an empty seltzer can on my desk.

      • Wildkitten :

        What’s bizarre about loving to wander around Staples?

        I’ll be looking at the Martha Stewart ARC aisle if anyone needs me.

        • Baconpancakes :

          LOVE the Martha Stewart office supplies. Those folders are just so happy!

    • Been There :

      Hugs to you. I don’t have kids, but I’ve been there when trying to find the correct meds / dosage for my depression and anxiety medications. I hope your doctor / psychiatrist is listening to your concerns and is taking an active approach. Hang in there! There’s bound to be the right mix for you. It might just take a bit to find it. In the meantime, yes to sunshine, yes to taking some time for yourself (even if it’s just 5 minutes to read quietly and send junior to his room to do something quiet), and yes to cinnamon, which I believe has been shown to lift moods naturally.

    • So sorry you are going through this. I’m in a similar situation but for completely different reasons. Can you try to find some time where you can be by yourself? May be take a day off or two from work when no one is around and spend the day as you wish? This obviously won’t solve the real problem but may make you feel a little better? I’ve been trying to figure out how I can improve my situation and in the process I’ve made a list of things currently bothering me, and ordered them based on priority (as in highest priority = happiest). I found it to be helpful whenever I feel overwhelmed because I think of this list and know that I need to work through the list to get to a happier mental state. None of this may help you, but hugs to you… you’ll get through this.

  2. I only wear flats at work.

    Favorite brands: LK Bennett (pricey), Ivanka Trump (inexpensive).

    For work, I stick to structured flats (no elastic sides) and mostly pointy toes. Minimal embellishments.

    I wear mostly pencil skirts and structured dresses to work, so that is what I wear them with.

    • preg anon :

      I don’t wear flats to work, but I do agree that pointy toe flats look better in a professional environment. I’m not sure why.

      • preg anon :

        I particularly think patent pointy toe flats look best.

      • Anon from 2:19 :

        I think they look sleeker and more intentional. I love round toe ballet flats for weekends/evenings (London Sole, etc) but they just look casual to me. Smart, pulled-together, but casual.

        Also, I do think that a rounded toe flat plus skirt/dress can skew little girl, which doesn’t happen with pointy toe flats.

    • too bad I'm so short :

      I don’t do heels unless absolutely necessary. I just think they’re uncomfortable (surely I haven’t found the right ones, yet), but I also hate having the dual-pants-hem conundrum. I don’t have many (any?) pants that I have hemmed for anything more than about 1.5-2″ heels, but most will do ok with flats too. I don’t know.

      I’m a flats girl. I can get away with just about anything at my office, so I’m not always on the lookout for nice flats, though I would love to expand my collection.

      I don’t like the super rounded-toe so much, but I like a rounded or almond toe better than a pointy toe.

      These are my most recent purchase–arriving tomorrow!

      • Cute, and good deal!

        I like this amount of toe point in a ballet flat.

        Great you can get away with this kind of flat at work, as these would also work great on the weekend.

    • I wear flats 100% of the time but they’re all round toe. I don’t disagree about pointy toes, but I think it’s harder to find a pair of pointy toe shoes that have more cushioning or an internal slight wedge. I’m obsessive about finding cute flats though and I’m wearing these right now: I think they happen to look great.

      I have a pair of arturo chiang pointed toe flats that have an internal wedge but they’re so unique i havent yet integrated them into my wardrobe. I’m also a size 9.5/10 and I just feel like they make my feet look huge. Even though I’m tall and it’s all proportional. Sigh.

      • too bad I'm so short :

        those Naturalizer flats are adorable. I love the 2-tone, especially in a classic color combination like that. As an aside, one of my earliest memories of my paternal grandmother is seeing her in a pair of navy/bone spectator pumps. I know they’re modeled after menswear, but I think that there is something undoubtedly lady-like and classic about them.

        • I can vouch for the naturalizer flats.. they look great and feel great. the first wear tore up my feet which was disappointing, but i’ve been fine ever since then. usually my feet dont respond that way.

          i also have a similar calvin klein pair that has a tortoise buckle but unfortunately they dont fit me properly

  3. preg anon :

  4. Anonylicious :

    One thing I’ve noticed, as spring has finally sprung and I’m switching from boots to pumps/buying more heels because they weren’t practical for my last job, is that sometimes you have to go smaller than you think in heels so that they’ll stay on securely. Or maybe my feet have shrunk half a size, who knows?

    • I can sometimes do that but because my foot is wide, I sometimes have to size up and wear a shoe with a strap. Also, I’m noticing that now that I’m not wearing tights, my heels are suddenly killing my feet. I think it’s just the transition. I’ve never had this problem before.

      • Anonylicious :

        Yeah, my problem is always that shoes that are wide enough tend to be too long, which makes me wonder if I really should be an X.5 wide instead of the next full size, which is what I usually buy.

        For some reason I really dislike wearing shoes with straps on them unless they’re flip-flops or something. Don’t mind them on other people, but I can’t stand them on myself.

        • I definitely should wear more like a 7.5 or 8 W rather than an 8.5M. But how many shoes can I find in my real size? Not many. I currently have one. And they are the pumps that fit my foot best and will stay on. They are a plain pointy-toe black leather Nine West pump with about a 2″ heel that I bought at DSW when I desperately needed shoes for my Dad’s funeral.

  5. I didn’t wear heels for about 10 years. When I started again, these are the things that made it easier:

    1) A strap around or near the ankle – makes a huge difference.

    2) Wedges are a good compromise, especially platform ones.

    3) Having enough room in the toe box is crucial, since your foot tends to slide toward the front of the shoe.

    4) Don’t wear heels every day.

    • DontBlameTheKids :

      And stretch! Don’t let your tendons tighten up.

      I agree that wearing heels every day is bad, but I have also heard that switching from heels to flats constantly increases your risk of injury. Here’s a link, but I’m not sure it’s the best one.

      • So, don’t change from heels to flats because it’s painful but do stretch to prevent the shortening? Shouldn’t you switch/walk in flats afterwards to also help stretch/prevent the permanent shortening? This article isn’t making much sense, kind of sounds like they’re saying it’s a foregone conclusion you will shorten your calves so don’t bother.
        I typically wear ~3.5″ heels 9 hours during the day (mostly sitting, but go for about a half mile walk during lunch in said heels), then go straight to the gym, switch to sneakers and run 8 miles afterwards.

        • Well, pin a rose on your nose!

        • I’m impressed that you can do the lunch walk in 3.5 inches! I am comfortable in heels all day but try to avoid long walks.

    • Ugh, my ankles have been much tighter since I’ve been wearing heels more frequently the past few months. I’ve noticed it especially in yoga. I wear flats to commute and don’t walk a ton in them but I can tell it’s affecting my feet. I’m going to try to be more cognizant of stretching my tendons- that seems like really good advice.

  6. hoola hoopa :

    Keep trying on heels until you find a pair that’s comfortable. The biggest mistake is to assume that heels are going to be uncomfortable and just putting up with whatever you tried on first. It IS possible to get comfortable heels that aren’t made for grandmas. You’ll likely find a brand that works for your foot.

    I recommend going to Nordstroms first. Their salespeople are so good at matching a shoe to your foot and needs.

    • Baconpancakes :

      I’ve had good luck with Cole Haan heels and wedges in the lower heel heights – they’re very comfortable for me!

  7. I agree with all of the above. I used to wear heels all the time in a place that practically required them. I stuck to relatively low Nine West ones, since those seemed to fit my large, wide feet the best (size 10-11). (Like the Nine West Flax Pumps). Just beware when walking down the stairs in heels — I once caught my heel in my pants’ cuff and landed at the bottom once! (I’m also incredibly klutzy.)

  8. I’ve been at a new job for about 6 weeks, but I was an internal hire – I’ve been with this firm in a totally different division for five years and have accumulated some vacation time (I have about two weeks worth) that I brought with me to the new position. How terrible is it to take a day off soon? My family is coming to visit for Easter and I’d love to have that Friday or Monday off but don’t want to make any missteps.

    • Totally a know your office thing, but I think an extra day around a holiday is probably fine. At least in my own office, a lot of people will be in and out of the office over the next couple of weeks because of religious holidays and their kids’ spring breaks.

    • Barring any important work happening at that time, I can’t imagine your supervisor objecting. If you’re you could do Friday or Monday, you could present it as “this is what I’m doing” and let your supervisor know that if one day is preferable for him/her, you’re flexible.

  9. shortperson :

    wedges wedges wedges.

  10. TO Lawyer :

    Re types of heels to try: I really like the Okala pumps by Sam Edelman. They have a lower heel, are really lightweight and have an ankle strap so they are really comfortable and easy to wear.

  11. Mountain Girl :

    Mary Jane or T-strap pumps are my go-to shoes. I find the the strap over the top of the foot keeps my foot from sliding or lifting out of the shoe when I walk and it allows me to not have to size down to keep them on my feet. At 40+ years old I have found that 20 years of wearing heels has taken a toll on my feet. I ignored all the advice in my early years about taking care of my feet and didn’t pay attention because my heels were comfortable and I could get around in them easily. But, alas, they have done some damage and a strap seems to allow me to size up a bit and keep wearing heels.

  12. IDoNotLikeTheConeofShame :

    OMG, this post was written for me. I broke my ankle 5 years ago and totally forgot how to wear heels.

  13. Warning: not all feet are created equal. I went to a podiatrist a while ago and he took an x-ray of my feet. He says “do your feet really hurt when you wear heels?” well of course they did but I assumed it’s normal. Not quite. My 2nd toe is longer than my big toe (ewwww). Apparently ~20% of the population has this problem.The doc said bc of this, when wearing heels, more of my weight is distributed on my 2nd toe rather than my big toe. The big toe and bones connected to it are bigger of course and thus meant to bear more weight. Inserts and practical footwear can help but nothing is better than a supportive quality pair of flats.

    Fortunately I’m tall and don’t really feel like I’m missing out on heels except my butt could use the lift they provide :-/

    • Anonytoes :

      “My 2nd toe is longer than my big toe (ewwww).”

      Why does this merit an “eww”? My toes are like this and I’ve always liked my feet. I think they look quite lovely and not at all malformed.

      FWIW, I don’t disagree with your doc’s diagnosis that this makes wearing heels harder (I struggle with them and don’t have the patience to go higher than 2.75″).

      • oh i used to get made fun of for it when i was a kid lol. im cool with my feet besides the fact that they always hurt.

        i found a lovely pair of booties that have a small platform so ultimately the impact of the heel is around 2.75″ and i feel great for a few hours but by the end of the night I’m in pain

        • Anonytoes :

          They run in my family and my parents totally went out of their way to tell me how beautiful my feet were-probably cause they were made fun of, too. It probably explains why my feet are my favorite part of my body!

          Your post was the first time it occurred to me that this might be the cause of my heel-wearing issues. Very few pairs feel comfortable to me. I’ve had the best luck with low-heeled Tory Burch and Steve Madden. I tried to wear my pretty Coach shoes the other night for a fancy event and am still in pain from the experience. Did your doc have any other tips?

          • No :( not beyond orthodics which probably isn’t even an option for heels. You’ve probably considered this before but try every type of insert, anything with a subtle platform, possibly Cole Haan’s Nike Air but imo a slight platform that offsets a 3″ or less heel is the most effective.

    • too bad I'm so short :

      Also, not all calves are created equal…I have a fairly low calf muscle, and so even with the “lengthening” appearance of my legs, because my calf muscle has quite a bit of volume low, where it attaches to my achilles, I don’t get that long slender leg. Instead, with my calves contracted like that, it sometimes looks like I have cankles. Low calves also sometimes make it hard to fit into tall boots…

      • Cornellian :

        That is fascinating and I think something that also affects my athletic very long torso-ed 5’4 frame.

      • Anonytoes :

        This is the other part of my problem ^^

        Faux cankles.

    • Cornellian :

      I think this is called Greek feet, FYI. Mine are sort of like that.

    • Anonylicious :

      Wait, that’s uncommon? I think most of my family’s like that. I haven’t noticed it causing any problems in heels for me, but that’s interesting to know.

    • Having a longer second toe is sometimes known as the Greek Foot. The Statute of Liberty has Greek Feet. I have the Roman Foot.

    • Miz Swizz :

      I read somewhere that people with a longer 2nd toe are better runners. Something about the shape of the foot.

    • I always heard a myth that if your second toe is longer than your big toe it means you will be the head of your household.

  14. I don’t agree that you need to skip socks/hose while breaking in shoes (not necessarily heels. I have always found that I need to wear new shoes with knee-highs or tights and then transition to barefoot. If I go barefoot breaking shoes in, I inevitably get blisters.

  15. Canyouwink :

    I’m by no means a heel expert but I have two bits of advice.
    1. Get heeled booties. The ankle support makes them much easier to walk in and you can get used to having some height. I have some Clarks Indigos that were inexpensive and are cute and comfortable. Also have a pair of Rag & Bone that are a little higher and are still very comfortable but they were expensive for an experiment.
    2. If you can, bring your heels to work and change there. Leave them at your desk but wear them all day to break them in. Then you’re not risking falling on the street and twisting your ankle and you can always take them off under your desk if your feet get tired, but you are getting used to walking short distances.

  16. Wedge is my solution!
    Even with 2-3″ wedge I can walk the whole day
    Even thick heels don’a allow such possibility

    • I don’t want to enter into the flats vs heels debate… although I always wear suitable flats and I (like to) believe they have contributed to my professional reputation…

      If you want to “increase your presence in the world” I believe it is worth exploring other ways of doing so other than heels… such as improving your public speaking or improving your posture… Maybe yours are already optimal, but I think both posture and voice contribute hugely to how we are perceived, more than heels/flats

      • Anonymous :

        + a billion.

        That made me die a little on the inside.

      • +2!

        I’m only in my mid-twenties, and I’ve already noticed heels taking a toll on my feet. Since I attempted to wear heels daily, I’ve had absurdly frequent foot cramps and can’t run without serious ankle pain. I’m not sure it’s worth it anymore :(

    • Same here I have to have wedges

  17. Modification? :

    Has anyone has a cobbler add a strap to pumps? To keep me from walking out of the heels

  18. I wear 3″-3.5″ heels daily. I think, though, comfort in heels is something you just have to learn. Part of it is learning how to walk and part of it is learning your own limitations. I can’t wear 4″ heels at all and I don’t even attempt it. But I can move pretty gracefully on 3″-3.5″ heels so I stay in that range. The second part is knowing how heels work. I typically buy .5 smaller than usual to accommodate for stretch. Sometimes, a whole size smaller, depending on the materials (suede stretches more for me). Finally, I think a person has much better presence in shoes they can walk in. Clients will be put off if you’re hobbling around or fidgeting constantly. It’ll hurt the way you present your confidence.

  19. Love heels and those Poc

  20. Those Pocos( in tortoise! ) are my absolute favorites. Can wear ALL DAY with not even a hint of discomfort.

  21. For me I started out with very small heels like the extra small ones on the end on riding boots then I went to wedges because they have a flat bottom to them

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