Kendall Jenner is arguably the most reserved member of the Kardashian-Jenner brood, which is why it can be easy to forget her bold street style fashion choices. While she's usually glamorous and sophisticated on the red carpet, Kendall's personal style is full of risks and surprises. From bringing back denim skirts to wearing tops that are hard to classify with words alone, here are Kendall's most experimental fashion moments.

The T-Shirt as a dress

Kendall, our hero, proves it is possible to wear only your favorite T-shirt to a high-fashion event.

The skant

Kendall has rocked the skant -- a skirt/pant combo -- more than once. And she has a point; why wear just a skirt when you can also wear pants?

The denim skirt

If you thought you got rid of denim skirts back in 2004, think again. Kendall is really trying to bring them back.

The long coat as a dress

As Kendall knows, layering can sometimes be too much, and sometimes wearing your coat as a dress is for the best.

The round, oversized glasses

Your mom's reading glasses never looked so chic.

The blue bib-type top

While we're still not sure what to call this, Kendall pulls it off.

The very low-cut and breezy top

It takes a brave and confident person to wear this kind of flowy top outside, where just a simple breeze could cause a notorious fashion blunder.

The sweatshirt as a dress

You know how sometimes you just put on an oversized sweatshirt at home and ditch the pants? Well, Kendall does the same thing. Except she adds a pair of heels and makes it something you wear outdoors.

The crop top to church on Easter (feat. Skant)

Just because it's Easter doesn't mean Kendall has to be off-trend. Oh, and hello again, skant.