I consider myself pretty irreverent when it comes to my style choices. “Life is too short to wear boring clothes”, said a Pinterest pin once. That does not mean I’m immune to being self-conscious when trying a new trend. My latest pilot project? The straight crop, high-waisted jean.

I’ve been seeing it everywhere on fashion blogs and I really love how it stands out among the sea of skinny jeans. So when I spotted a pair of medium-wash Levi’s on sale for $24.99, I snagged them before I could read too much into why they were in the discount section.

I took them out for a spin yesterday, and although I didn’t feel the same confidence that perfect dark-wash skinnies give me, I felt bold (ish). I felt a wee bit like a sailor wearing a denim version of their culotte trousers at first, But it won’t be long before these catch-on and skinny jeans are officially out.

In the meantime, here are my style inspirations for this new denim cut.

How about you trendsetters? Any looks you still feel slightly self-conscious about, but love to rock anyway?