The "Ugly" Shoes We Actually Want to Wear
So it’s 2018, and we’re still talking about “ugly” shoes which, if you ask me, means that the microtrend has some serious staying power—and how could it not? After all, what’s more intriguing than an item that’s universally considered to be somewhat unappealing to the eye yet is simultaneously highly embraced and celebrated at the same time?
Such is definitely the case with the three shoe styles we’re calling out today. From clunky to dad-inspired to super-scrunched, they’re the shoes we simply can’t help but love, and neither can our favorite street style stars. See them in action below and shop our favorite versions of each trend while you’re at it.
1. Super-Slouchy Boots
While when it comes to boots, we typically consider sleek to be the main goal, as of late, the less polished but definitely more intriguing slouchy boot has been top of mind.
Shop our picks:
2. Dad Sneakers
Simply the name "Dad sneakers" should be enough to keep us away, but for some reason, we can't help but lust over the constant stream of inspo we're seeing on not only street style stars but models and celebs as well.
Shop our picks:
3. Clunky Ankle Boots
Remember what we said about typically favoring sleek boots? Well, the new wave of lug-soled, utilitarian-inspired ankle boots is the second shoe style in this roundup to make us want to change our ways.
Shop our picks:
Since starting as an intern back in 2013, Nicole Akhtarzad Eshaghpour has held several roles here at Who What Wear, and she is currently Editor-at-Large. Upon joining, she was a senior about to graduate from business school at USC. Fast-forward to 2025, and she's moved to NYC from her hometown of Beverly Hills and spends her workdays a little differently from when she was just starting out. Currently, she focuses on a weekly mélange of shopping content and her Trust Me—Buy This newsletter. As far as her personal style goes, she's largely drawn to neutral, classic pieces but will always make an exception for something colorful or bejeweled as long as it's deemed worthy enough. After all, the only thing she loves more than a party is dressing up for one. On her downtime, she can usually be found at home eating something delicious and trying to force her husband to watch Summer House.
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