Winter Shorts: Attempts 1 and 2

So, I've tried wearing my $24.99 H&M winter shorts twice now. The first time, I wasn't brave enough to venture out wearing them. The second time, I managed to wear them to a small gathering at a friend's house. 

Where: Playing "dress up" in the privacy of my own home

What: Potential casual night out outfit

The other components: black tights (Target), black Dolce Vita booties (now marked down to about $125), white Target tee, random black/white/grey slouchy sweater from Ross.

Where: Friend's place in Smyrna

What: Football-watching, casual "night-in" (cheering for Dan's team, the Cowboys)

The other components: argyle tights (Dillard's), grey slouch boots (from Steinmart, via my lovely friend Kate!), black elastic art deco belt (Salvation Army), H&M black tank, brown short sleeve cardi from Target

I must admit that wearing these shorts is a little stressful! I'm not usually one to wear shorts (even in the summer), nor show a lot of skin in no matter what I'm wearing. I think I'll feel more confident if I wear them with opaque black tights next time.

Winter Shorts: What's the Verdict?

Photo (and related article) from www.chicagonow.com - here

Winter shorts... love them or hate them? You know, those cuffed shorts (often wool, houndstooth, checkered, etc.) that you've been seeing a lot of lately.

I can't decide, but I'm leaning toward "love." I guess "leaning toward love" really means "like," but whatever...

I bought a black pair from H & M recently and am currently trying to decide how to wear them. Ideas?