Why I Can’t Let Go of Shoes That Cause Me Pain

Eight Philly Mag staffers on the shoes we hate to love.


So cute; so painful. | Lauren McGrath.

Of the myriad things men will never understand about women, the one that tops the most lists are those token pairs of so-painful-we-can-hardly-walk shoes that we keep around anyway. Sure, we’ll complain about them the entire night. We’ll regret the decision for at least a week, as we nurse the blisters on our toes and heels. We’ll swear up and down that we will never wear those damn shoes again. Yet they are impossible to part with, and so they languish, mostly unworn, in our closets.

Why do we do this to ourselves? The answer is simple: for the love of all things fierce, for the way shoes can change your outfit and your outlook in one simple (albeit painful) step, and for the hope that maybe, maybe, one day our feet will shrink or our heels will become immune to blisters and we’ll be able to happily walk in them. Think you’re alone in this feeble dream? Think again. Here are eight Philly Mag staffers on the shoes we hate to love.

Claudia, Photo Editor


Claudia’s Forever 21 round-toe pumps. | Lauren McGrath.

Where do they hurt? “Hm. Where don’t they hurt? Because the arch in the shoe is higher than other pairs I own, most of the pressure is on the ball of my foot. Oddly, there is enough room in the toe area but my pinkie toes always seem to bear the brunt of the pain.”

Longest you’ve lasted in them? “I lasted a mere two hours in these, but not before I totally bit the dust. At Davios. For our company Christmas party. My very first company Christmas party.”

Why do you keep them? “The color! The shape! The chunky heel! I’m 4’11” so any shoe that elongates my stumpy legs will forever stay in my closet – even if they do squeeze the life out of my pinkie toes and leave my arches aching all night long. I always seem to get complimented on them, by men and women alike. Anything in the name of confidence-boosting, right?”

Emily, Lifestyle Editor


Emily’s Alexander Wang peep-toe booties. | Lauren McGrath.

Where do they hurt? “Even though the heel is fairly chunky, it’s pretty high – five inches –and there’s hardly any cushioning on the sole, so all the pressure is on the balls of my feet. Which I could deal with, only the peep-toe part cuts into my toes, so they’re doubly vicious.”

Longest you’ve lasted in them? “A few hours standing, or a day at work (during which I mostly sit).”

Why do you keep them? “The glossy color, which is divine. The weird Velcro strap. I keep them in my office to look at, and sometimes I’ll throw them on for a few hours. You know, when I’m sitting.”

Lauren (me!)


My neon cap-toe pumps. | Emily Goulet.

Where do they hurt? “Ball of the foot within about three minutes; all ten toes go numb after five.”

Longest you’ve lasted in them? “After almost a year of them collecting dust in my closet, I busted out these bad boys for an event in Old City. As parking is impossible in that part of town, I wound up walking about six blocks to the restaurant. On cobblestones. Alone. I looked like Bambi being born in the forest, and got about three flat tires per block (ya know, when your heel slips out of the shoe and it makes a terrible sound as the stiletto part drags against the ground and everyone looks at you like you’re an idiot who’s never worn heels). I swore to myself, ‘never again,’ as I do every time I wear them.”

Why do you keep them? “They’re the sassiest shoes I own; I can’t part with them. They make me feel like a combination of boss girl/fashion blogger. Every time I’ve managed to shuffle around in them, someone always stops me to comment on how much they love the damn shoes.”

Adjua, Health & Fitness Assistant Editor


Adjua’s Jeffrey Campbell boots. | Lauren McGrath.

Where do they hurt? “They hurt pretty much all over, but mostly on the heels where there’s a hard piece of the structure of the shoe that pokes me at all times. When I take them off, it actually looks like an animal attacked my foot.”

Longest you’ve lasted in them? “I wore them to DC once and made it through a night at a concert with lots of dancing, all while managing to hide the pain. Then when I left the bar, my friend and I were walking to a late-night Ethiopian restaurant when he decided he just had to carry my because I was walking too slowly and weirdly (shoe pain, obviously), and he was worried we’d never actually get to the restaurant. They were the only shoes I’d brought with me that weekend. The next morning, my beat up feet and I went to DSW.”

Why do you keep them? “A few weeks ago, after a long bout of refusing to believe that I would not want to kill myself while wearing them, I finally sold them at Buffalo Exchange. They cost me $200 and I got $10 for them which is absolutely depressing. [Editor’s note: Should have sold ‘em on Depop!] But, save for the scar tissue that’s built up around my heels (really), my feet are pretty much healed from their wounds, so there’s that.”

Alyse, Art Director


Alyse’s perforated leather pumps. | Lauren McGrath.

Where do they hurt? “They hurt the front of my feet the most, but it doesn’t take long for them to cause my entire foot to be in pain.”

Longest you’ve lasted in them? “I actually bought them for my sister’s wedding, but quickly realized that I would die if I had to wear those the entire ceremony. Also, with the platform on those babies, there was a very high likelihood that I would trip down the aisle (I wasn’t interested in testing that theory out). I decided to only wear them to the office on days I knew I would be sitting a lot.”

Why do you keep them? “I love the shoes; I think they are super-cute and perfect for spring. I can’t convince myself to get rid of them. For now, they sit in my closet. Usually I wait until I forget how uncomfortable they are and then wear them again. It’s a vicious cycle.”

Julie, Art Director


Julie’s heeled loafers. | Lauren McGrath.

Where do they hurt? “The heel is so thick your stride gets weird. And then the ball of the foot starts to ache. It takes it time, but they’re pretty bad after about 20 steps or 20 minutes.”

Longest you’ve lasted in them? “For an on-the-street shoot I did for work. I wanted to look put-together, and they are my most put-together shoes. Four hours later, I could not walk. I was seriously considering going barefoot, but I did that once out of desperation – not a good idea. Usually when I am wearing them, I have another pair to change into.”

Why do you keep them? “Um, did you see them? Need I say more? No one ever compliments them, but I believe that’s because they are just too fantastic. It’s like telling a hot guy he is good looking – why build the ego?”

Alexandra, Wedding Assistant Editor


Alexandra’s suede booties. | Lauren McGrath.

Where do they hurt? “My arches are cramped within two minutes of putting them on; if I’m actually walking around in ‘em, it’s only a few minutes before I can’t feel my feet at all.”

Longest you’ve lasted in them? “If I’m feeling particularly confident, I’ll wear them to work and go a full nine hours – but by then, my legs are so weak that I’m literally hobbling home. Recently, I wore them to an after-work happy hour, and I was the epitome of girl-who-can’t-walk-in-heels as I dragged my feet down Market Street to the train station.”

Why do you keep them? “I bought them because I wanted a black, (relatively low) heeled bootie that could be both causal and dressed up. They definitely serve that purpose, but the arch is much higher than my flat feet can handle. But they’re cute, so I deal with the pain.”

Ginny, Sales Coordinator

Ginny’s colorblocked peep-toe pumps. | Lauren McGrath.

Where do they hurt? “Ball of the foot – within the first minute you feel regret. They cause me to look like a baby giraffe walking for the first time whenever I wear them. Ugh.”

Longest you’ve lasted in them? “I bought these specifically for one of my college a cappella concerts. Our concert was 16 songs long. I cried when I finally was able to take them off three hours later. I had to wear Uggs for a week after due to Post Traumatic Heel Disorder. Haven’t worn them since, and that was winter of 2011. Yikes.”

Why do you keep them? “They’re the most beautiful combination of blue hues. I hope that one day soon my feet will shrink down, and I will be able to wear them again. Maybe I should just suck it up and do it for the sake of fashion.”