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? 

The Hunt: Silk Button-Front Blouses

The Best Silk Button-Fronts | CorporetteSure, we all know what basics professional women are supposed to have in their closets, but if you’re buying one for the first time or replacing one you’ve worn into the ground, it can be a pain to find exactly the right incarnation in stores. In “The Hunt,” we search the stores for a basic item that every woman should have.

We rounded up some of the best crisp button-downs around this time last year, but we haven’t ever rounded up the best silk-button fronts.  I’m still a fan of the ones with a pointed collar (instead of a rounded or band collar, or a split neck) for a more classic look — the collar looks great beneath a suit blazer, layered underneath sweaters, and more.  For my $.02, I’d suggest wearing a cotton camisole (with the arm holes adjusted fairly high) beneath them so you can try to get at least two wears before you have to take them to the drycleaner.  There’s a ton of selection out there — readers, which are your favorite silky button-downs?  Do you have any laundry tricks (either to extend the wears-per-launder or to make them look nice without drycleaning?) Any must-haves (or do-not-buys?) [Read more...]

Professional Women and “Empowering” Clothes

empowering clothesDo you find it “empowering” to dress how you want?  Do you think confidence gained by clothes is 100% of the answer for work — i.e., if it makes you feel confident, you can wear it to work?  There was an interesting discussion here — years ago now! — that I just took another look at, and thought would be a great jumping off point for discussion today.

I recently saw someone comment on an old post that another commenter’s words had stayed with her through the past few years, so I took a closer look at the discussion. The post was on patent leather heels — a reader wrote in wondering if they were appropriate; my counsel at the time was to be wary and avoid “eau de hooker,” as I so delicately called it, but that by and large patent leather heels were just fine for most jobs.  The real fun started in the commenting section, when another blogger named Samantha wrote in to disagree with me: [Read more...]

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...]

I Can’t Wear a Suit — But Want to Show Authority

I Can't Wear a Suit But Want to Show Authority -- How? | CorporetteWhat do you wear when you want to show authority without wearing a suit?  We’ve talked about what to wear when a suit doesn’t feel right, but Reader R is looking for authoritative clothes that aren’t intimidating and travel well…

I recently started a new job as in-house counsel. As part of my responsibilities, I will be traveling internationally to conduct audits and give training sessions. The job is great, but I’m not sure what to wear! My de facto would be to wear a suit, but my boss suggested that I should avoid wearing suits, since the appearance of a “suit” tends to make people nervous. Some relevant factors: (1) I’m often the only woman in the room; and (2) I’m also often the youngest person in the room.

Basically, I need pieces that say, “Position of authority, but non-scary” and travel well. Help!

Congrats on the new job, R!  One of my older friends was a lawyer for a TV network in the 80s, and I remember her telling me that she would leave her suit jacket in her office when she had to go talk to the comedy writers or producers — it was less intimidating, less “this is coming from The Man.” So you’re not alone in wanting to thinking about what your clothes say to people.  For my $.02: Put some thought into exactly what response you want from people.  For example: Do you want them to respect that your word is the final word, and they should do what you tell them? (Play up the authority.)  Do you want them to come to you with problems that might not be communicated to the home office otherwise?  (Play up the approachability, but keep some authority.) Do you seek to really understand their problems and make friends in the office? (Turn the authority way down.)  (As for the “looking younger” part of your question, you may want to look at our older post on the difference between acting young and looking young at the office.)

For my $.02, I would go with what you feel most comfortable in, and modify that (taking into account, obviously, the office culture for where you’re going). If you’re comfortable in: [Read more...]

The Best Clothes If Your Weight Fluctuates

What to Wear if Your Weight Fluctuates | CorporetteWhat wardrobe items should you invest in if you’re losing (or gaining) weight?  What clothes will fit even if you regularly fluctuate by 10-20 lbs?  Reader K wonders what the best clothes are for someone dealing with weight fluctuation:

I have a story idea; the work wardrobe for the weight fluctuator. Me and many of my friends bounce around by 10-20 lbs. It is expensive to buy everything in two sizes. I thought it would be helpful to do a post on the type and style of clothing to invest in if you want to have an office wardrobe that works when you’re up or down.

For instance; I have a lot of wrap dresses as they are forgiving and flatter across a 15 lbs spectrum. Sheer blouses can be belted in at any weight. I own a lot of dresses as they can be belted in if I’m training for a half marathon or without a belt they’re more forgiving after Christmas party season. I steer clear of non-stretch, and very fitted fabrics as they tend to look bad when too tight or too loose. I make sure to buy work pants with belt loops so that they’re not falling down after an ugly breakup has left me without an appetite. A longer camisole with a blazer over it can hide if I can’t do up the top button on my pants. Fitted work shirts can be paired with a camisole if the buttons won’t close over an increased chest.

This is a fantastic question, and I’m so curious to see what readers will say — we’ve talked about when to give in and buy a larger size, as well as how to keep a working wardrobe while losing weight — but we haven’t talked about this.  When I was younger I regularly fluctuated 10-20 lbs, generally in the same clothes — but when I was at my thinnest, I found that even a few pounds made my pants fit differently, so I knew pretty quickly when I was gaining.  Now that I’m heavier, of course I’ve said that I don’t want to invest the money in a good wardrobe because I’ll inevitably lose the weight (right? right!?) — but I’ve found that there are a few items that I can buy now that, for whatever reason, I can imagine being great even if I lose 10-20 pounds. So here’s my list:

[Read more...]