My pedophile-esque Terry Richardson glasses. My elementary school principal used to wear a pair like these... yikes.

Stella McCartney $1180.00

These dinosaur platforms are what ugly cool dreams are made of.

TOPSHOP $160.00

Channel a 1940's schoolboy with these high-waisted wide-leg cropped bad boys. Add suspenders for ugly cool bonus points.

Rachel Comey $334.00

I can't say for sure but it looks to me like Rachel Comey was inspired by the Jewish garb called "tzitzit" for this one.

TOPSHOP $96.00

Grandpa's magical cardigan.


Oh the clunkiness of these clowny oxfords! Janelle Monae would be all about these.

NastyGal $15.00

Nothing like white ankle socks and black shoes to add a dash of ugly to your look.

NET A PORTER $350.00

A boxy 90's denim vest. YES.

TOPSHOP $110.00

Capri trousers: so ugly, they're cool.

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