(via Shutterstock)

It’s one of those big fashion dilemmas that all of us will face at one time or another. On the one hand, we want to be comfortable. We have busy lives, valuable time, and more important things to worry about than whether our arches are aching or our heels are going to get stuck in brick streets until we fall on our faces. On the other hand, we want to look good. It sucks to see a beautiful pair of shoes at the mall, fall passionately in love with them, and know that they’re going to drive us crazy the whole time we’re wearing them.

(Related: Tell Us How You Feel About Wearing Tights Under Shorts)

Personally, I make different choices on different days. If I have PMS or a blister from working out, there’s no way in hell I’m wearing anything that doesn’t feel like an enchanted pillow on my feet. If I need a pick-me-up or to feel confident in a big meeting, though, I’m all about the heels. I think a lot of my fellow ladies feel the same way. But here’s the REAL question: How do we feel about ultra-comfy shoes that are just flat-out… ugly?

(Related: Tell Us How You Feel About Accutane)

It seems like every single season, someone comes up with a new design that’s supposed to be the ~ultimate solution~ for the bad reputation of comfortable shoes. Sketchers put out a line a few months ago that are supposed to look like cute boat shoes despite actually being grandma shoes. TOMS are trying to reinvent themselves by being available at cheaper prices and in more convenient places. People are trying, and I appreciate that. But we still haven’t really nailed it. Shoes that hurt are still hot. Shoes that feel good still look bad.


(via Shutterstock)

So I’m wondering, dear Gloss readers, what you think. Do you wear Crocs? Or Birkenstocks? Or any of the other classic ugly-but-comfy shoes? Do you think they’re worth it? Do you actually like the way they look? I’m interested in knowing. Drop us a comment below to tell us how you feel, and maybe we can solve this mystery together, once and for all.

We’ve always been able to count on our readers to bring awesome insight to the comments section, so we’re giving you guys a chance every Thursday to tell us how you feel about new trends! Click here to see the Tell Us How You Feel About archives.