The Ugliest Shoes of 2020, From Least to Most Outrageous

ugliest shoes of 2020


Szymon Brzóska/The Style Stalker

Whether you love them, feel indifferent, or want to go run and hide at the thought of them, you can't deny that ugly shoes are dominating the conversation this year. There's no doubt we've hit peak "ugly." We can hardly scroll through Instagram without seeing a pair of Chanel's orthopedic sandals or go a week without hearing about a buzzy new shoe trend that claims to be uglier than the last.

Now that a new year is upon us, we took it upon ourselves to recap all the shoe trends that we can't unsee. We went on and on about all the "dad" sneakers in our lives, pointing out how women paid above retail just to own certain styles. In the warmer months, it's all about sporty sandals that we saw everywhere (and will continue to see). Then there are the less aggressively "ugly" but equally noteworthy trends like chunky Chelsea boots and old-school heeled loafers that are quickly becoming a thing as we move into the new year. But that's just the tip of the iceberg—2020 will see some of the ugliest shoes to date (and by ugly we mean that precise combination of ugly-pretty).

Not all of these trends were made equal—some are far more absurd than others as designers continuously pushed the limits. So, which trend did we crown the ugliest of all ugly shoes? Keep reading to see our definitive ranking.

Level: Light

The Trend: Chunky Chelsea Boots
ugly shoes of 2020: chunky combat boots



Standard combat boots are getting an upgrade this year with a chunky, platform sole and the look is as cool as it is comfortable.

Level: Mild

The Trend: Heeled Loafers
ugly shoes of 2020: loafers with heels



We'd categorize heeled loafers as "grandma" chic and the retro style is coming back in a major way for 2020.

Level: Lukewarm

The Trend: Toe-Ring Sandals
ugly shoes of 2020: toe-ring sandals


Collage Vintage

We can see why toe-ring sandals are intimidating, but trust us, this warm-weather shoe lends a cool touch to any outfit.

Level: Boundary-Pushing

The Trend: Thick-Soled "Dad" Sneakers
ugly shoes of 2020: Nike's M2K sneakers



Ahh, good old "dad" sneakers. When it comes to these throwback kicks, the chunkier the sole, the better.

Level: Thought-Provoking

The Trend: Chunky Sneakers With Jagged Soles
ugly shoes of 2020: Fila Disruptor sneakers



This level is the same as "dad" sneaks but taken up a notch with a jagged sole like Fila's iconic Disruptors.

Level: Polarizing

The Trend: Flip-Flops
ugly shoes of 2020: flip flops



Flip-flops are hardly polarizing when you're heading off to the beach. But styled with for the streets? It's a tricky look that more and more fashion insiders are testing out. 

Level: Shock-Inducing

The Trend: Orthopedic Sandals
ugly shoes of 2020: sport sandals


Szymon Brzóska/The Style Stalker

First Chanel came out with their version of an orthopedic sandal complete with thick velcro straps, a platform sole, and a heel strap. Then, of course, the fashion world took the idea and ran with it and now every version of the "grandpa" sandals exists.

Level: Pot-Stirring

The Trend: Lug-Sole Sneakers
ugly shoes of 2018: Eytys chunky sneakers



Chunky sneakers are one thing, but sneakers with the soles of heavy-duty boots? They're in a category all their own. 

Level: Jaw-Dropping

The Trend: Hiking Boot-Sneaker Hybrids
ugly shoes of 2020: Gucci flashtrek boots



Sneakers? Boots? Why choose when hybrids like these exist. They may take a little warming up to, but the streetwear crowd has fully embraced the hiking look.

Level: Downright Outrageous

The Trend: Z-Coil Sneakers
ugly shoes of 2018: Christopher Kane z-coil sneakers


Christopher Kane

Last, but definitely not least, we present you with the "ugly" shoes to end them all: crystal-embellished z-coil sneakers à la Christopher Kane. 

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