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? 

How to Look Professional With a Wool Allergy

professional nonwool sweatersWhich are the best sweaters if you suffer from a wool allergy?  Are there any other tricks for looking professional while avoiding wool? Reader P wonders:

Like a lot of people I seem to know, I am allergic to wool. It makes me itch. Even cashmere. Even soft merino wool. Even if the sweater is a mixture with only 5% wool. My question is–where do I find good quality sweaters made of silk, linen, cotton or other non-wool fabrics that are light enough to wear under a blazer or suit jacket in the winter?

We’ve talked about how to look professional in cold weather, but not the allergy question, which is something I’ve gotten a few times over the years — let’s discuss.  I’m curious to hear what the readers would say here. A few suggestions — [Read more...]

The Best Commuting Shoes

The Best Commuting Shoes | CorporetteWhat are the best shoes for walking to work?  Reader J wonders…

Can you do a post on commuting shoes? I always change into my heels at work, and I need help finding a pair of comfortable (but cute) shoes to wear on the subway/walk to work. I’m curious what shoes other readers wear on their commute.

Great question, J!  We’ve talked about how some women commute in wedges, as well as taken polls on whether toning shoes are appropriate for a commute, but while I’ve mentioned “commuting shoes” a lot, I don’t think we’ve ever had a post devoted to my own perfect version of commuting shoes.  Here are the factors I’ve always looked for:

[Read more...]

How to Find Shoes for Your Weird Feet

How to Find Comfortable Heels | CorporetteA lot of women have problem feet in one way or another — wide feet, narrow heels, fallen arches, bunions, weak ankles, size 11, size 5, etc, etc, etc. I’ve gotten a few questions from readers and I thought it would be an interesting discussion — how DO you find comfortable heels and shoes?  We’ve talked about comfortable heels before (of course; it’s one of our top posts!) but not specifically about how to find comfortable shoes. (Pictured: Buzzfeed had a fun guide to shoe storage earlier this year…)

I have a few ideas, but I’m curious what resources the other readers may know about… [Read more...]

How to Campaign for Flexible Working Conditions (Or, How to Change the Company Policy That Requires You Lug a Heavy Laptop Around)

How to Campaign for A More Flexible Workplace (Or: How to Ditch Your Company Laptop)How do you campaign for accessibility and flexibility in your workplace when the policies are less than ideal?  Yesterday’s post on how to lighten your tote bag got me thinking — I was so intrigued by the commenters who noted that they have to carry a huge, bulky laptop to and from the office because that is the the only approved way to get access to the office system.  When I was working in BigLaw, my firm used Citrix to give everyone access to the Docs Open system and other office programs — there were even times you could access document review programs from home.  (Ah, glory days.)  The only thing we needed to access the system was a small, flat device (a 2″ by 1″ fob) that displayed a long number that changed every thirty seconds. When you needed to log into the system, you entered the current security number.  That was five years ago, so it honestly didn’t occur to me that companies with information security issues would not be using something similar to Citrix in 2013.  (Even the Department of Defense has a better remote access option, according to a 2011 Lifehacker article.)  Maybe there are good reasons Reader R’s company isn’t using a secure remote system — but maybe it’s just an old policy that hasn’t been reevaluated in a while or from the right perspective. 

So readers, let’s talk about this — how do you change an office policy to make the conditions better for you (and those who come after you)?  Sheryl Sandberg talked a bit about this in Lean In — regarding how she insisted that the Google parking lot have spaces reserved for expectant mothers — and this was kind of mentioned in a recent NYT article about workplace flexibility  — but I can’t seem to find much else about this topic on the Internet.  For my $.02, here are some ideas… [Read more...]

How to Lighten Your Load

how to lighten your loadIf you’re carrying a million bags, how do you look professional?  How can you lighten your load and reduce the number of bags you’re carrying? Reader R wonders…

I work in a large corporate environment and recently had a daughter. I’m back at work, but I feel like a bag lady. I’m only 5’3″ and have to carry in my laptop, purse, pump, lunch, and coffee. (Not brave enough to add my gym bag to the mix, although I’d like to.) I feel like the bags overwhelm my frame and generally make me look smaller, younger, and unprofessional. How do others juggle all this STUFF?

Congratulations on your daughter, R!  Great question — I can see how this is a problem for new mothers, but also for other people carrying too much stuff.  We’ve talked about what your tote bag says about you, as well as how to save your back while commuting, but we haven’t really talked about a) how to lighten your load, and b) how to balance your load (particularly if you’re petite) so it looks more managed.

From my perspective, most of reader R needs to do is to reduce the amount of stuff she carries.  Some tips: [Read more...]