and cute to boot!

I'm not one to follow trends, clothing/style trends that is. It may be because I don't want to look like every other girl walking down the street or simply because when I try to pull off the current trend, I fail miserably which then leads me to use the excuse of not wanting to "look like everyone else."

Sigh...

Which leads me to the main reason for writing this post. I want to rock the mid-calf boot, and I want to rock the hell out of it. I've never worn a boot, let alone purchase a boot and I'm not one to spend massive amounts of money on shoes or anything for that matter; I'm certainly not a spendthrift by any stretch of the imagination. But, when I happened upon this boot, I fell in love and felt more than willing and happy to spend the 90 bones these babies cost (and yes, I'm aware that $90 is actually not much to spend on a boot, especially when I saw boots for $325, but $90 for me is significant!)

Behold, the Steve Madden Candence Boot

Pulling up to my house today I spotted the perfectly boot-sized Amazon box, quickly parked, grabbed the box and ran into the house, throwing my purse to the floor and ripping the box open in an excited frenzy. I slipped off my flats and pulled the beautiful leather over my leg only to discover that my legs need to go on a diet, or try annorexia for a little.... something! The boot fits perfectly, but a bit too perfectly. I can fit a finger or two between the boot and my leg (side note: I don't have fat calves but they are definitely muscular after all the running and shredding I've been doing) which means that a skinny jean is going to be difficult to fit into the boot, leaving me with the option of leggins.

Like I said, I rarely rock a trend (normally because I don't know how) and I've never worn a boot... so, I now own a boot, but now what do I do?! Leggins scare me but I've never worn them so maybe they aren't as scary as I think. If I wear a leggin with the boots what do I wear on top? I need some ideas!

(These looks are super cute but, not gonna lie, they are going to make me look like I'm wearing a potato sack - not the look I'm going for, fyi)

Anyone have the same issue? Do you have muscular calves that preclude you from wearing the many cute boots you see girls with toothpicks as legs prancing around in? (no offense to the toothpicks out there - I envy you more than you'll ever know). Have you found a boot that fits you perfectly? Any go-to's for sweaters/shirts/accessories/etc. to wear with boots and leggins?

What trend have you attempted recently that you were worried about, but then totally rocked it out?