How To Wear Heels To Work More

September 6, 2016 by Justine Schwartz
shefinds | Style

I am guilty of wearing flats every chance I can. I just love them–I have a pretty decent collection of ballet flats, loafers, espadrilles, etc., and I’m not averse to wearing them even when I think other women in the room might be wearing heels. Blame it on the fact that I have a long commute or extremely arched feet, but flats are just my happy place.

I know I’m not a trailblazer in saying so (duh, who wouldn’t prefer slip-ons over sky high heels?), but here’s where I’ve had a revelation recently: my boss would prefer if I wore heels more, and they actually *do* make outfits look instantly dressier/more serious. It’s a little bit old school, but wearing something with a small heel over say, a sneaker, can be the footwear equivalent of “coming from a place of yes” to your boss. It’s in the category of dressing for the job you want–look around at the female managers in your office–what do they wear? (For the record, I don’t think women *need* to wear anything to be successful at work–that comes down to your performance!). They also just look good, a great heel can be supremely flattering and cool, so it might be a matter of personal taste and wanting to elevate your overall work style.

For *whatever reason* you might want to wear heels more at work, here are some tips I discovered for doing so:

READ MORE: How To Make High Heels Comfortable

Invest in two comfortable pairs. Not all heels were created equal–some cheap heels are supremely uncomfortable, while others are specifically designed for comfort (like my personal favorite, the Cole Haan Cassidy boot made with Nike Air technology). If you’re not already wearing heels to work every day, chances are that the pairs you own aren’t comfy enough. Invest in two new pairs to get started–a pump or sandal, and a bootie.

When shopping, don’t just look at the heel height as an indicator of how comfortable they will be (shorter does not always mean better), read the reviews, too. Some brands are specifically designed for comfort, like Corso Como, Naturalizer, Aerosoles and Easy Spirit. Obviously, most of us want shoes that look good, too, and in the high-fashion category, Loeffler Randall’s pumps seems to be the big winners.

Loeffler Randall Pari Pump

Loeffler Randall Pari Pump ($350)

Tape your third and fourth toes together. If you still have foot pain no matter how “comfortable” or low the heels are, try this trick for wearing heels with no pain: using medical tape, tape your third and fourth toes together (obviously this works best with closed-toe shoes, but you can use clear or flesh-toned medical tape in sandals). This will take the pressure off the balls of your feet and is a proven trick for making heels more comfortable (runway models do it!).

READ MORE: How To Look Taller Without Wearing Heels

Break your shoes in (even if they’re old!). If heels give you blisters or just tear up your feet, they might not be properly broken in. Here’s a good trick for breaking any shoe in (new or old, flats or heels): put the offending shoe on with socks and walk around your home. The socks will accentuate the parts of the shoe that aren’t fitting right (it will feel even tighter). Once you’ve determined where the shoe is too tight, use a hair dryer to blow hot air on that spot, stretching it or pushing on it with your hand or a heavy object.

You can also stretch them using the ice trick: fill a freezer bag with water, put it inside the shoe, then put the shoes in the freezer. As the water freezes to ice, the bags will expand and stretch out the shoe.

Keep a pair at your desk. This seems really obvious–but it seriously works, especially for us lazy girls and commuters who really only want to wear the heels at work and nowhere else. Keep a bootie and a pump or heel stashed in your drawer or hidden away in a tote bag or box (beware of shoe bandits!! They’re worse than the people who steal food out of the fridge!!). If you keep them under your desk, be aware of how they might smell–just to be on the safe side, you can always stick a dryer sheet or a few drops of baby powder inside to repel the stinky feet smell.

READ MORE: These Are The Socks You Should Be Wearing With Heels

Start once or twice a week, and build up your endurance. Just like training for a marathon, getting back in to heels takes practice. You don’t want to burn out and tear up your feet and have to be out of commission for a week.

Set a calendar reminder for the first 3 weeks. To break your routine of wearing flats every morning, you should create alerts on your iPhone that will help you remember to plan outfits to go with the heels, tape your toes, etc. It takes 21 days to break a habit, and until then, you’ll need rely on these notifications to remember. (It sounds really involved, but creating an alarm or a cal event takes two seconds!)

[Photo: Brooklyn Blonde]


Editorial Director

Justine Schwartz is a veteran women's lifestyle editor; she's written extensively about style & beauty tips, health advice and wedding planning for more than a decade. Her work has appeared in New York Magazine, Huffington Post and New York Weddings. Justine has been with SheFinds since 2010; you can reach her via email at [email protected]

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