I mentioned last post that while I wear heels on most days, it was not always so. I used to wear flats. All. The. Time. That’s because they’re comfortable, and I couldn’t get used to wearing heels. I was working as a personal stylist at a major luxury department store, and my 12-hour work days were filled with running around, so I sacrificed that aspect of my style for comfort. That is until one day my boss told me (and I quote) “You always wear such great outfits, but then you have flats on, and it ruins everything. I need to see you wear heels more often.”

Time to learn to wear heels, ladies!
It sounds cruel, but remember I’m in the styling business. And more importantly….she was right!
So I trained myself to wear heels, it wasn’t hard or painful, and now I wear them almost constantly because, truly ladies, they do look better. As in, a lot better. Flats are still OK sometimes, but wearing a heel is what pulls everything together and makes you appear more ladylike and sophisticated as well as grown up. If you are the way I was, and you can’t stand wearing heels even out to dinner, fear not. Here’s how it’s done….
Step one: Get the right fit. This is vital. If the shoe is too small, your toes will be crammed. If it’s too big, your foot will slide forward and put all the pressure on your toes, and none of the straps will fit correctly. Your heel will also slide out. Neither way is workable or comfortable, so don’t do it. Go to a higher-end store like Neiman’s, Saks, or Nordstrom and have them properly measure your feet. You don’t need to buy your shoes there, but it would be beneficial to try a few pairs on that the expert picks out, so you know what a good fit feels like.
Step two: Start easy: wear a low wedge heel. A wedge is stable enough to keep you from wobbling, and the low heel height will keep your feet from getting too sore. A wedge also distributes your weight more evenly than a stiletto, so they are the most comfortable. Start by running errands in them, a couple hours at a time. Work your way up to wearing them all day.

start with a low wedge heel like these from Zappos
Step three: Work your way up gradually. You should try a taller wedge next, then a low stiletto.

Darling little gold Cole Haan heels from Zappos
The transition from wedge to stiletto can take some time, as it’s an entirely different feeling, and may even require you to adjust your center of gravity as you’ll be putting most of your weight on the heels of your feet.Take your time getting used to wearing them all day long.
Step four: Buy the most gorgeous high heels you can find! You’ve made it! Once you’re used to wearing a low heel all day, the transition to a taller heel is nothing, you won’t even notice it.

Gorgeous red Louboutins from Saks Fifth Avenue. HOT!
Some helpful tips:
1. If necessary, invest in some good insoles to give you the proper support.
2. Take good care of your heels! Get them re-soled if necessary, polish them, protect them with dust bags if possible. Also, don’t drive in them as that chews up the heel. Take them off when driving, put them on when you arrive. I do it every day, it’s really not a hassle.
3. Avoid strappy heels when you’re first starting. Those can be the most painful, and it won’t be easy to endure them when you’re not used to heels in the first place.
4. Try on lots and lots of heels before you buy them, this is the best way to get an idea what is really a good fit and what is actually comfortable.
5. Walk around the shoe department as much as possible when considering buying a pair. That’s how you’ll know if you’re going to wobble, if the straps will rub on your feet, or if your heel will pop out the back.
My final notes:
Of course it’s still OK to wear flats, as I still do sometimes, and I’m not suggesting every one wear heels every day. That wouldn’t fit everyone’s lifestyle and it wouldn’t work for everyone’s style. I think wearing heels is simply a good way to present yourself better, and to feel more put together, and if it’s something you’re interested in, this is a good way to get started.
Lastly, I would say expect to invest in quality footwear, but my last post about my $10 heels disproves that! So what I will say is, don’t expect heels that fit well and wear well to be cheap. You might strike the gold mine of cheap comfort like I did, but that can’t be the standard. Better shoes do cost more, most of the time.
I hope this helps you transition to heels, it certainly worked for me, and it’s been totally worth it!