By: Michelle

Okay, confession time…I HATE heels. I love how they look, but hate how they feel. Now Olivia chooses the best, highest, most glam heels out there and rocks them every time. However, I can’t seem to get over how uncomfortable they are. And, if I’m being totally honest with myself, I know I’m a hot mess and am not the most graceful swan of the bunch.

Sure, I can go on with my life never again wearing heels, but they are so damn cute! Besides, for a girls night out, or fancy affair, heels just look more appropriate than flats. Instead of settling, I hunt down the perfect pair. Trust me, it’s out there.

Now they say platforms are typically more comfortable, and I do agree. But, unfortunately, it’s not exactly the ‘in’ look of the moment. We want to be comfortable without sacrificing fashion, right? I am in my 20’s after all, it’s far too early to go for the orthopedic look. So, what is in style? Strappy heels; specifically, two straps. These are so classic, I love the look, and they cause pain, like A LOT of pain. By the end of the night, my feet are bright red and would scream if they could.

So, now what? There are pointed toes, stilettos, booties, mules, and whatever else you can think of, but what is the most comfortable fit? Well, if I’m being honest, any heel with prolonged wear is going to cause a little discomfort, but with the right amount of champagne and proper shoe structure, you might just be able to get through the night!

If you’re anything like myself and don’t consider yourself very heel-savvy, here is what you should look for in your perfect shoe…


Real leather is the best bet for a comfortable shoe. Real leather stretches and overtime will conform to your foot. Yes, they can be a little more expensive, but think of them as a custom shoe. If you don’t have time to break them in, get a pair thin socks, or sockettes, dampen them, and wear the heels around the house for a few hours. The moisture and heat will stretch out the leather and they will be ready-to-wear in no time. Think of it as your ultimate housewife moment—wearing heels while doing the dishes.

Recommendation: Sol Sana Aubrey Heel

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If you want to avoid falls at all cost, rough up the soles of the shoes. Grab some sand paper or go rub the soles against some brick or concrete. If the heels are on the pricier, more designer end of things and you want to preserve the look, you can buy stick on grips instead. The hope is that this will have you strutting your stuff with confidence and avoid looking like Bambi on ice. You don’t want to be that girl in the club suffering from a non-alcoholic induced face plant.

Recommendation: Kendall + Kylie Hailey Boot



If you think your feet are going to hurt no matter what, try some insoles. You know, Dr. Scholl’s? Depending on the shoe, gel padding can make all of the difference. However, if your shoes are already a little snug, insoles can just make them tighter, so play around with it before really committing.

Recommendation: Raye X Revolve Charles Mule

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Stilettos look nice, but chunky heels are just as nice. At the end of the day, heels are heels, and lucky for us, chunky heels are in. When you’re in a stick-think heel, you tend to place more weight on the balls of your feet and tend to feel more pain. With a thicker heel, you can distribute your weight more evenly and hold out just a little bit longer.

Recommendation: Tory Burch Loretta Embroidered Platform

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Whether you are a heel lover or not, you must ALWAYS pack bandaids. Blisters can honestly ruin a whole night if not dealt with properly. You can pre-prepare with blister pads, or deal with them as they come. The point is to make sure you are able to deal with them. Blister pain is one that cannot be ignored.

Recommendation: Steve Madden Dove Slingback

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P.S. Whatever you choose, just don’t choose wedges. Wedges are so NOT cute. Anyways, here’s to good nights with happy feet!

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