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

How to Start Wearing Heels | CorporetteHow 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? 

Can You Interview in 4″ Heels?

Can You Interview in 4" Heels? | CorporetteAre 4″ heels too high for job interviews?  Is a red sole inappropriate for interviewing and networking?  Reader A wonders…

Hi I was wondering if I could get some advice on shoes. I will be starting law school in the fall and I’m wondering what heels would be appropriate. I currently own a black leather pair of Louboutins that are 4 inches. Do you feel it’s appropriate to wear them with the red bottom showing? Also is 4 inches considered too high? Thank you!

We’ve talked about Louboutins at work here, as well as which heels are too high, but we haven’t talked about either issue in a while. (Pictured: Christian Louboutin Simple 100 Leather Pumps, available in store only at Saks.)  Here are some general tips:

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The Best Splurges

The Best Splurges || CorporetteWhat items are “worth the splurge” if you have a healthy amount of discretionary income? Reader S wonders…

Here’s my idea for a post – what are the central items that are “worth the splurge” for those of us with a healthy amount of (but not unlimited) discretionary income? I’m thinking there are certain purchases – the classic Burberry trench, a Chanel clutch – that would be well worth the amount spent, since you’ll potentially be using the item for a decade or more, but what are some non-obvious items that would fit into this category?

FUN question, reader S!  There are definitely things I bought in my 20s — when I was single and making six figures at a law firm — that I wouldn’t necessarily buy now, with a husband and kiddo in the mix (at least not without thinking about it looong and hard).  Since I’ve always known that my weight tends to fluctuate, most of my splurges have been in the accessory category. Here’s my $.02, but I can’t wait to hear what the readers say…

My top splurges:

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When Should You Wear Pearls?

1.indexedWhen is the right time to wear pearls?  We’ve talked about how to buy pearls, but Reader C sent in a super short email wondering when to wear them…

One of my favorite jewelry pieces is my strand of Mikimoto pearls that I got for my 30th birthday.  They were an investment piece, and they get so much wear that I’m glad I did invest in a quality piece.  That said, there are a ton of price ranges (and there’s nothing wrong with faux pearls) so there’s something for everyone.  For my $.02, when to wear pearls depends on the kind of pearls we’re talking about: [Read more...]

How To Buy Quality Pieces Without Looking Old

Armani jacketCan younger women buy quality suiting pieces like Armani and St. John’s, without looking old?  Reader J has an excellent question:

I recently bought this Armani Collezioni jacket on an impulse. The price was too good to pass. But after I got home and tried it on a few more times, I start to wonder if this jacket would make me look too old if I pair it with a black skirt or a pair of black pants. I’m in my mid 30s and I thought this jacket could add 10 years if I appear all in black. What do you think? What should I wear with it to show the fine detail of the Armani design without adding 10 years to my age? I’d really appreciate your advice.

What a great question.  I think some pieces — particularly higher-necked, conservative pieces — can tend towards looking a bit “older”.  Here are a few tips off the top of my head for how to look your age, but I’m really curious to see what the readers say: [Read more...]

Professional Watches for Women

Which are the best watches for professional women? Is it still worth investing in a quality watch, even though everyone uses their cell phone or computer to check time? Reader L wrote in to ask about watches:

I searched your site and found the post on digital watches, but I would love your (and your readers’) opinions on non-digital wrist watches. It would be useful to hear suggestions at various price points.

This is a great question. I’ve written before about how I think watches are still status symbols. Not only do men’s magazines all still advise men to go out and spend money on a watch, but I’ve often been at a lunch with high-achieving women, looked around, and noticed that 8 of the 10 women there were wearing Cartier watches.  In New York — at least among the legal and banking set — Cartier is kind of the first and last word, at least in my experience. My 30th birthday gift to myself was a Cartier Tank Francaise watch, though, so perhaps my perception is a bit biased! (It was a huuuuge splurge for this Midwestern girl.) [Read more...]