Hi. I'm Sheridan. I'm 5'11", a size 18, a Leo, and I barely wear heels.
Sure, I've bought a ton of heels, but in recent years I've noticed how little I actually wear them. Here are some reasons why:
1.) I'm tall. I still remember one night when a date asked me why I was wearing heels since I "already have the height" — as if that's the only reason I would be wearing them. That's one way to kill your strut.
2.) I'm plus-size. I know I can't speak for everyone, but a lot of plus-size women could probably attest to the fact that growing up, we sometimes didn't want to draw attention to ourselves. And heels equals all the attention.
(Actual footage of me at a middle school dance).
3.) I wear a size 13 shoe. Yep, you read that correctly. That's a one and a three. When I say it's hard to find shoes in my size, I mean it'd be easier to convince producers to make a black man the next Bachelor.
4.) I'm just a casual person. I love sweatpants, I love T-shirts, I love sneakers. I love to wear things that would let me run away from walkers when the inevitable zombie apocalypse happens.
This all brings me to my challenge for the week: wearing heels every day for seven days. Here are the rules:
1.) I must wear a different pair of shoes every day — no repeats.
2.) I must leave my apartment with heels on.
3.) Only — and if only — they cause too much pain to function, I can take off my heels in the afternoon.
So let's do this.
Day 1: The Red Wedding.
On Sunday I went to my cousin's wedding in Altadena. I decided to wear a pair of wedges that have been sitting in my closet for what feels like forever. When you know there's going to be lots of standing, walking, and even dancing involved, you should wear a wedge. Basically, I was like, "I'M GONNA OWN THIS."
Now wedges get some flack for not being "real" heels but joke's on you because this wedding was outside. Guess whose heels kept on getting stuck in the lawn? Not mine because I was wearing WEDGES. I floated gently on the surface, laughing my evil laugh as heel after heel sunk into the ground below.
After the ceremony, we made our way to the terrace for cocktail hour and that's when it dawned on me: My. Feet. Hurt. K-A-R-M-A.
Lots of people complain about walking in heels but that's never been my problem. For me, standing in heels for a long period of time is like trying to hold your pee. At first you're like "I feel great, I totally don't have to go" and then all of a sudden the pain hits you and you're pushing little kids out of the way to get to a stall.
This is me at the end of the reception with my sister and mom. You see my smile?
YOU SEE THE PAIN? THERE'S NO SOUL IN THESE EYES.
This was truly a red wedding. Not because my entire family got slaughtered in front of me but because I'm pretty sure I felt like my feet were going to start gushing blood at any moment.
Day 2: No crybaby here.
Since I had to wear a human dress and inhuman shapewear the night before, I decided that I was totally allowed to relax on day two. That meant trying to do the impossible: wear sweatpants with heels and not look like a fool. I went for a high school wrestler-chic palette of gray and black for dinner with my mother and in-laws.
For heels, I looked to a strappy number that I knew wouldn't give me too much grief throughout the night. Though L.A. isn't exactly a walking city, I needed a pair of heels that wouldn't make me want to scream somewhere between where we parked and the restaurant.
These heels certainly held up their end of the bargain. The heel itself was sturdy enough that I wasn't worried about snapping my shoe apart. My only main concern was the balls of my feet. Padding was basically nonexistent so I could really ~feel~ each step I took.
At a few points throughout the night, I couldn't help but think, I'm a badass lady rocking heels on a Monday. I felt... invincible.
I finally started to understand why women want to wear these things all the damn time. Putting on heels made me, who has horrible posture, walk with her head held high. Plus, my hips did that back-and-forth thing that Joan owned on Mad Men. I felt like a freakin' queen.
This was literally me.
By the time I got home that night, I was feeling cocky AF. If I could masterfully walk in heels after two glasses of pinot grigio — there was nothing I couldn't do.
Day 3: My Left Foot (and my right one, too).
As a large-footed lady, I tend to gravitate toward sneakers and flats that are a little too big for me. I'd much rather be swimming in shoes than experience the pain of toe cramps. That's why I ignorantly thought a pair of too-big wedges were genius. How could they hurt me if they didn't suffocate me?
After pairing my bright green, escaped-from-Studio-54 wedges with my Where's Waldo shirt from the Spring Couture collection, I walked out of the apartment with a strut like no other. I was ready, these heels were the best decision ever.
BUT HAHA GUESS WHAT HAPPENED NEXT? THAT'S RIGHT, ONE TICKET TO OUCHTOWN ON THE OUCHIE EXPRESS WITH A LAYOVER IN OUCHIEVILLE.
How did this happen? Turns out wearing a pair of shoes a little too big for you is the same as being a little too snug and it's just your optimist outlook telling you otherwise.
So here I was, lalala not a care in the world, when I felt the balls of my feet become more and more raw. Since the shoes were a little too big, my foot kept on sliding up and down, up and down. It was like the shoe was a cheese grater and my foot was about to be the topping to a steaming hot plate of crap this hurts pasta.
Me trying to keep it together.
Taking off these shoes at the end of the night was a sweet, sweet relief — the kind of relief you get after holding in a stomach-squishing fart until you get to your car and let it rip until you can't rip it no more.
Day 4: The day my legs got to feel air for the first time since the Scientific Revolution.
There are two main reasons why I don't wear dresses and skirts that often. 1) The chafe struggle is a chink in my armor, and 2) Shaving is always on the bottom of my to-do list. But this is a new and improved Sheridan. This Sheridan wears heels. This Sheridan can wear a skirt. And boy am I glad I did because I was all about this outfit — so much so that I Instagrammed it.
I chose a pair of pointy-toed heels that appeared to be super comfortable. They had a nice layer of padding for the balls of my feet, so I was feeling this look hard.
Unfortunately, like 30 Rock and cookies 'n' cream milkshakes, all good things must come to an end. By the second half of the day, my feet felt hot and blistery, and the leather was rubbing up against my toes causing what the scientists call foot sweat.
You know how you'll be like "OMG I love spooning, let's cuddle" and then after a few minutes you're like "Hey nevermind, it's too goddamn moist so can we please stop with this madness?" Yeah, that's my love affair with these shoes. It was such a good idea at first. By mid-day, it was such a tragedy.
It truly is a shame though; I felt like such diva in this look. But what can you do? Your feet want what your feet want, and by 2 p.m. my feet wanted a pair of flip-flops.
I wasn't sure how to feel after today. At this point, I had one excellent experience out of four. The odds were certainly not in my favor. Though each day I found myself more and more excited to pick out an outfit with my heels, by the afternoon I was so over it.
How could I capture that glorious moment from the morning and keep it throughout the day?
Day 5: When I was questioning my will to continue this godforsaken experiment.
This was supposed to be fun. So where did it all go wrong? Apparently with a pair of mid-size gray suede heels. Out of all the outfits, this was probably my least favorite, just because you can tell that I was trying too hard to make something work.
Just like trying to understand an Iggy Azalea freestyle, nothing made sense in this look. But this is about the heels. After today, I know that thin heels are not my favorite thing in the world. They hurt every inch of my foot. It's like I ran the New York Marathon when the only marathons I run are usually on Bravo. As you can even tell from the photo, my curled-up sausage toes were even turning different colors.
Yet I had to look deep inside and ask myself, Are you, Sheridan Bonita Watson, a quitter? Technically yes — I did quit violin, flute, ballroom dancing, volleyball, shotput, chorus, soccer, and field hockey, BUT YOU KNOW WHAT I MEAN. I was going to turn this day around because I knew with the power of positive thinking, anything could happen.
After work, I went out to dinner. I did the sensible thing and changed into a chunky pair of what I could only describe as gladiator heels. It was the biggest mistake of my life.
You might think I'm overreacting but I promise you this was a disaster. I don't even want to post a picture of the heels I changed into because I'm pretty sure I sent them back to Hades where they belong. But I will show you a picture of my feet post-dinner so you can see the struggle.
LOOK AT MY FEET. LOOK AT THEM. LOOK AT THEMMMMM.
My husband thought it would be funny to laugh at me while I was trying to hobble home. In the words of Princess Buttercup, "YOU MOCK MY PAIN."
Day 6: I actually can't tell if I'm still alive or not.
We're getting toward the end of the journey, the sweat is in my eyes, my legs burn with the fire of a thousand suns (or something else deep IDK). If I thought the previous days were going to be bad, I knew day six would involve ALL of the running around.
The only way I would get through this with the sanity of myself and my loved ones (aka the people I've been complaining to about my swollen feet for the past week) is if I wore a pair of frat-house wedges.
What's a frat-house wedge? Well, it's a name that I totally didn't make up just now. It's a go-to shoe that will take you from your apartment to the Row for a frat party. Of course, it's not just about frat houses, it's basically any going-out shoe you have that could have survived the Revolutionary War. Beer could be spilled, falls could be taken, and these shoes would stay firmly on your feet.
A good frat-house wedge can make you do this:
It was a miracle... my feet didn't really hurt all day. I don't know if it was the adrenaline or not but I was still standing by the end of the day.
I was able to walk without wincing in pain, move easily up stairs, and even drive. Together with my simple-as-can-be outfit, I was feeling good (the Nina Simone version). Was I exhausted at the end of the day? Absolutely — walking in heels works your leg muscles like no other.
But I was excited to learn that I can enjoy a pair of heels even after five previous days of betrayal and tragedy (and yes, I have been told I'm dramatic before). If every pair of heels made me feel this good throughout the day I would get rid of all my Converse*.
*That is a lie, I have a weird attachment to my high school shoes even with the emo lyrics I wrote on them when I had ALL of the feelings.
Day 7: Will these heels kill me? Let's find out.
I went for it: the laced-up, see-through, tall and thin heels. I was willing to accept the torture.
But I was fine. I walked with confidence, and didn't even notice if my feet were in pain. Were these shoes actually the most comfortable things in the world or had I just come to a point where I've blocked everything psychologically? Who knows. All I can say is by the afternoon I was still able to walk with a swagger in some pretty grown-up shoes.
In fact, I was feeling so good that I was convinced to go to — gasp — a bar!
That joke would have been funnier if you knew just how much I love staying home. Like, you better be getting married to Chris Hemsworth for me to get off of my couch (though I would be getting off of the couch to kill you and assume your identity immediately).
But you know what, I was feeling on top of the world. Since I survived an entire week of wearing heels, I deserved a drink. And not just a pinot grigio — I was going to have tequila.
Wearing heels to bars is always shady business. Heels can break, the floors can be slippery, you could stumble down some stairs because for some reason every bar is dark AF. You try to order a drink but all that comes out is "Harrumphma" because your feet hurt. Luckily, this pair of booties served me well. I was so comfortable that I was able to let my confidence flag fly. I wasn't self-conscious about my weight or my height. I was a warrior and this was my armor.
When I got home, I wasn't in a hurry to unzip these bad boys. And only when I woke up the next morning did I realize that though my official challenge was over, my journey with heels wasn't going to end there.
So, what did I actually learn throughout this whole saga?
1.) Anyone can wear heels. Doesn't matter what height or size you are — if you want to rock heels live it up.
2.) You don't have to wear heels every day or be 100% against heels. There's a gray area, feel free to play around with your taste.
3.) Don't have false expectations. If you have a pair of heels that always hurt you an hour into wearing them, don't think that it'll magically stop happening after a while. That's like going to karaoke and hoping that some drunk person won't butcher "Livin' On a Prayer." You know it's going to happen, and you have to live with the consequences.
There's a reason I don't wear these. But they sure do look pretty.
4.) Heels can make you feel like you're on the top of the world. It's not just the height, it's the way they force you to walk with a little pep in your step, and how wearing them can make jeans and a T-shirt look put together. I'll tell you, this week is the first time I've felt somewhat like an adult in my entire life.
5.) Sorry but size matters. Don't con yourself into thinking you'll "stretch" the shoe eventually. Don't buy a bigger size thinking it's easier to deal with. If it doesn't fit, it doesn't fit. It's OK.
Tl;DR: Whether you're painting the town in your favorite stilettos or rocking a pair of flats, keep on killing it.
