10 Pairs of Ugly Shoes You’ll Actually Want to Wear

 When I was in middle school, back-to-school shopping was a big deal. Not for the Trapper Keepers and gel pens (though let’s face it, they WERE the sh*t), but for the shoes. Every year, I got one pair to start the school year off with — a single pair that would define my style for the next 365 days. I had no interest in the practical, reliable sneakers my peers all wore, however. I wanted heeled, strappy sandals.

“They go with everything,” I stubbornly insisted to my stepmother.

When she pointed out the impracticality of open-toed shoes in the winter, I only argued harder. “I’m only going from the car to the door. I’ll be careful!” I proclaimed.

Needless to say, I lost that battle.

Cut to 20 years later.

While I still love a good heel (you’ll rarely, if ever, catch me in the loathed sneakers of my youth), I’ve also found myself drawn to another, more “sensible” alternative: the cute ugly shoe.

Don’t worry: I’m not going to try to convince you to wear the heinous Crocs or Fenty slides that Drew Barrymore and Rihanna would have you put on your feet, because let’s face it: There’s not enough star power in the world to justify that. I will concede, however, that flats, loafers and even mules (!) have begun finding their way into my closet at an alarming rate.

Check out my top picks below!

Please note: This post contains affiliate links. 

1. Kristen Cavallari Charlie Loafer ($150): It’s rare that I readily accept trends with no questions asked (see my review of NYFW latest for proof), but when mules rolled on the scene as the new “it” shoe in 2016, I was ready for them. Maybe it was my status as a newly cemented 30-something, or maybe my bunions were hurting that day, but for whatever reason, I welcomed these little eyesores with open arms and I have never looked back. *Shrugs* 

2. Chinelas Babas ($95): Chicago-based brand Chinelas, which means “slippers” in Argentinian, embraces its “ugly” status with the Baba — a new spin on a traditional Moroccan design which enables you to fold the heel down for an easy loafer-to-mule transition. They also happen to be ridiculously comfy … plus the leopard print is kinda’ cute, no? 

3. Steve Madden Karisma ($80): Yes, I know these are gaudy as f*ck. I am also aware they are cheap Gucci knock-offs. And yet, still, I desperately want them. They have just the right amount of eccentricity to punch up a basic outfit, and for $80, they look rather luxe, if I do say so myself. Who needs height when you have this much character!?

4. Kork-Ease Challise Clog ($149.95): Another famously hideous silhouette comes to us in the form of the born-again clog, and I’m not ashamed to admit that I would wear the sh*t out of these monstrosities. Don’t let that 3.25″ block heel fool you — there’s a cozy little padded footbed in there complete with arch support that’s justtttt right for those of us that aren’t quite ready to let go of our stiletto heydays. 

5. Rothy’s The Flats ($125): In addition to embracing unsightly styles in my 30’s, I’ve also developed a much keener interest in where my clothing comes from. I’m not perfect, by any means — my closet is still chock full of Forever 21 finds — but I have adopted several new eco-friendly faves, such as Reformation, Everlane (the waste from their jeans goes into bricks to make affordable homes) and now, Rothy’s. These moisture-wicking, knit shoes (available in four styles) are made from recycled water bottles! Better yet, they’re machine washable, and, when you’re done with them, you can send them back to the company to be recycled. Genius! 

6. Rebecca Minkoff Alexis Mule with Studs ($75): These are wrong in so many ways — one could easily mistake the oversized bows for tied on plastic bags — but also so, so right. I can’t quite seem to tear my eyes away from them any more than I could a beautiful pair of Louboutins, and really, what more could you ask for in a shoe?

7. Katy Perry Collections The Artist ($99): Leave it to Katy Perry to turn her footwear into a literal object d’art by modeling it into a crayon (Or a a shark. Or a boat). These colorful creations, which come in such fun shades as Sunflower yellow and Queen’s Cloak purple, make getting dressed just as fun as any 4” stunners might.

8. Topshop Alice Pointed Mules ($40): Red shoes are my kryptonite. Just like Kit Keller couldn’t lay off  the high fastballs in A League of Their Own, I can’t lay off the red kicks. Add in the fact that these ones are made with vegan leather (I prefer it to animal carcasses, what can I say?) and feature a croc print and I’m over the moon for them, lack of heels and all.

9. YRU Lavish F*ck Shoes($90): There were the first pair of flats to ever capture my full attention (I can’t imagine why?). I bought them on a whim roughly three or four years ago, and still, they’re in heavy rotation in my wardrobe. While they’re admittedly not for the faint of heart — they get a reaction everywhere I go — they ARE every bit as badass as a pair of booties. 

10. Charlotte Olympia Kitty Flats($415): I’ve made no secret of the fact that I’m a cat lady through and through, so naturally, these velvet ballet flats hold great appeal for me. Screw sexy footwear: These have EARS and whiskers!!!!! Me-ow! 😻😻😻

What shoe is your favorite? Tell me in the comments below! 

Xo, Nicole