I have a problem.

For almost two years now I have been living in black leggings. They are comfortable, functional, stretchy and work perfectly with boots.

But I’m ready to move on.

My goal this Fall is to transition from leggings to jeans as my “go to” leg-wear. I have never been too fond of how I look in jeans. I’m nearly 6 foot tall and curvy, which denim-makers seem to over-look as a possible body type.  It’s near impossible to me to find jeans that work.

Today I found myself killing some time at the local mall. I sort of wandered into the Gap not really expecting to find anything, but wanting to wander around none-the-less. And then a sign caught my eye.

40% off all denim.

Wow. That seemed like a good deal.

So I scoured the shelves, picking out my size in every wash and style they had available.

Jackpot.

My Pile O' Jeans

I found two styles that really worked well for me: Curvy and Long & Lean. I ended up by two pairs of the Curvy (dark and medium wash) and one pair of the Long & Lean (dark wash).

It wasn’t until I was happily flinging my shopping bags into the back of my car that I realized something.

I don’t know what shoes I can wear with these jeans!

Both styles are flared, which is cute – but doesn’t work well with my closet full of boots. How do you wear boots with flared jeans? Fold them over and stuff them into the boots? What about ankle boots? What about my Toms?

And here lies my dilemma. What shoes would you suggest? Do you wear boots under flares? I’d love to hear what you all think!