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 heels — under 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.
• 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?