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10th Commandment: Professional High Heels

Readers often write in to ask me about what the different office dress codes mean.  What are the differences between conservative, professional, creative and business casual?  How do I know which category my office falls into?  The easiest way to tell is to look at people’s shoes.

A hard and fast guide?  No.  But you show me a woman’s shoes, and I can probably tell you where she works.

Closed-toe with a moderate-high heel?  She’s probably in a professional or conservative environment.  If she’s wearing nylons and she’s under the age of 55, her office dress code is probably on the strict side.

Does she have on shoes that would look at home on a runway, a red carpet or the pages of Vogue?  She probably works in a creative environment like PR or advertising.  Or does she wear ballet flats, sneakers or flat boots?  Her office is probably business casual (unless it’s Friday, and then who can tell?).

For the next three days, we’ll have posts that use a pair of shoes from each type of office as a base for a few work-appropriate outfits.  And we’re going to start with the conservative/professional crowd.



Ann Taylor Eryn Kitten Heels ($128)

I don’t consider 2.5″ a kitten heel.  This miniscule lift is a kitten.  Instead, I think that a height between 2.5″ and 3″ is the most comfortable choice for most women.  I can run all day in an under-3″ heel and get home at night with just a mild twinge of discomfort.  You can go up to 3.75″  (maybe 4″ if you’re on the smaller side) before the shoes start to look too high for a professional environment.  But if you’re at all concerned, I’d be cautious and stay under-3.5″.

I think Ann Taylor pumps in general are the most comfortable brand on the market right now in a mid-price point.  They’re padded in all the right places and cushioned without being clunky.  I also like the Perfect Pumps that come in at 3.25″, and these menswear-inspired Valerie heels at 2.75″.

Looking for other closed-toe shoes in a medium heel height?

J.Crew has three options to choose from: the pointed-toe Everly at 3.25″, the Valentina D’orsay at 2.75″ and the Sloane, round-toe heels at 3.5″.  The Corso Como Del pumps also come in at 3.5″ for a price of $129.

Prefer something in the under-$100 price range?  These suede Asos Skittle heels come in at 3″ even.  Michael Kors also makes a great, basic Flex heel in a mid-height of 3″ and a lower 2″ heel.



  1. Liz says:

    Any suggestions on what styles of heels look good with tights, particularly the thicker type? Thanks!

    October 1, 2013/Reply
    • Belle says:

      I like round toe shoes with tights MUCH better than pointed toes. The points can look a bit matronly. Or try high heel, tall boots.

      October 1, 2013/Reply
  2. Amanda says:

    I’m cursed with wide feet. Any suggestions on wide-width shoes?

    October 1, 2013/Reply
    • AttiredAttorney says:

      The comfort plus pump at Payless. Seriously. I get asked if they are Cole Haan’s ALL the time. In the fake leather colors they look, well, fake, but in the patents, they are amazingly comfortable, come in wide widths, and cost under $30 (under $20 this week!).

      October 1, 2013/Reply
      • Amanda says:

        Thanks! I never would have looked there.

        October 1, 2013/Reply
        • D says:

          I second the recommendation. i got the tortoise ones recently and got several compliments!

          October 2, 2013/Reply
  3. Zenithar says:

    I just got a pair of these Easy Spirits and was seriously impressed by how comfortable they were:


    I am really hard on shoes and while I love the look and comfort of my Dels, these have taken a serious beating and still look brand new. For those Hill ladies scrambling around the marble floors, a rubber sole is a godsend.

    October 1, 2013/Reply
  4. Rachel says:

    FYI, your ASOS links back to the J. Crew Sloane pumps.

    October 1, 2013/Reply
  5. emery_j says:

    I’ve had great success with DvF pumps. They are very well made and even include a padded triangle sewn into the ball of the foot area. And you can get them on sale ($150ish or less).

    October 2, 2013/Reply
  6. april says:

    I like your ideas for hills. However I a lobbyist and after walking from office to office on the hill yesterday, even my ballet flats were killing my feet. I have a vast collection of all sizes of heels, but in my older age, almost 40, I am trying to be comfortable as well as fashionable.

    October 2, 2013/Reply
  7. save. spend. splurge. says:

    I find J. Crew heels to be the most uncomfortable on the market. Ann Taylor’s are much better, or Cole Haan…

    October 3, 2013/Reply
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