I like big boots, and I cannot lie...

This is the time of year that this Northern Girl can't get enough of tall riding boots!  Easiest. Outfit. Ever. Skinny jeans, tall boots, plain sweater and a scarf - or - blazer and some chunky jewelry.  Leggings with a dress! Dress it up, dress it down. Whatever.  Heels or flats. Personal preference. 

Here's some inspiration!

Leggings, tunic and scarf! (And Starbucks!)

Jeans, funky tank, chunky cardigan!

My only real suggestion - a good quality boot that you are comfortable in.  (If you go super cheap, you might just end up with sweaty feet and legs trapped in plastic.)  Find one that is versatile - not too tall (can't look like a hooker at work!) and not too short (it'll cut your calf in half and make them look meatier than most of us want them to look.)  Booties are a whole other blog ;)  This year's trend is hardware on your boots.  Very cool and chic this time of year!

And if you are trying to camouflage your rear end, check out that second inspiration picture... the tank is fitted but the sweater swoops down to cover the butt.  And besides, everyone will be checking out your sweet boots, not your butt.  ;)

So, if you've been hesitant to try this trend, be brave!  You won't regret it. 
LP

PS... these are my favorite brown boots by Jessica Simpson (Macys).  I could live in these - they're amazing.  And you can wear them high or fold them down.  A multi-purpose boot!