Lauren, I love your look! I wear leggings frequently, because I can peel off a jacket or a thin top layer, put on some dance shoes, and rehearse or take class.
I have a few ways I wear them - the main way is the way Lauren wears them in her photo - over the knee boots, jacket, cadet cap, etc. I love an equestrian, or military look - or something that evokes a man's costume in a film or ballet, such as Valmont, or the Russian dancers in Nutcracker.
I also wear them with heels and a sleek, fitted jacket - and I usually will reference photos of Wolford's 2011 and 2012 lookbooks online - Spring/ Summer and Fall/Winter. It's a fun alternative look for drinks and dinner out with friends, or if I'm going to a casual show or concert. I always get compliments on this look.
I like to reference ninistyle.net, she does some really fun stuff with leggings.
In warmer weather, I will put on a couple of thin layers of tops: camis from Forever 21 (shockingly, these last for years), and tissue-tees or those little sweater boleros that Target has had for the last couple of years. I'll wear this with ballet flats or dance sneakers that I use for streetwear. I almost never wear open-toe shoes because I live in a city, and the stuff that is on the sidewalk... well... the idea of my little pink toesies going anywhere near what is on the sidewalk... it doesn't bear thinking about....
My leggings are all by Max Studio and Theory, straight leg and bootcut. They last years, and have good substance to them, so they actually look like pants, and not glorified tights. They have a good cut to wear with a shorter tops, without feeling like I'm showing my ladyparts. (I somehow felt like Will Ferrell in Anchorman, typing that last bit).
I rarely tuck in - only it's been a very very clean eating week for me, and if the blouse ruffled and dressy and drapes pretty. I put a corset-type belt around my waist and some boots, and again, the look is equestrian.