Even though I live in Las Vegas, the temperatures still drop it drop it low, girl.  It's cold, like crank-the-thermostat-up cold.  Bring on the boots and booties!  Boots?  Check out the 10 Commandments of Wearing Brown Boots.  Booties?  Ohemgee, help, so many options, what is hot, what is not?!  I have some advice. 

1.  Going to break your ankle?  Might as well break it in multiple places!   Add more visual breaks in the line of your foot with scrunched up socks, leg warmers, fringe or fur trims.  The contrasting width of the bunchiness will actually slim your calf and leg.  Notice how bucket-like Ugg boots make legs look more "twiggy."  Bunchy socks, fur, and leg warmers create the same effect.   See right picture.

2. Pucker your lips, NOT your booties.  It appears as if the shoe doesn't fit correctly when there is a big pucker or gap between the ankle and the top of the shoe.  Boom.  You now have cankles.

3. Create a vertical line with laces.  Lace-up booties can be especially flattering because a) the shoe fits your ankle tightly, giving you the slimmest ankles, and b) the vertical line created by the laces draws the eye vertically up your leg. Hey, sexy!

4.  Bare legs?  Get nude.  Cold weather doesn't require dark footwear... it's okay to lighten up.  Nude pumps elongate your leg, duh, so why wouldn't nude booties do the same trick?  They do!  See the examples above.

5.  AVOID the worst bootie silhouette ever-- higher front and lower back.   I'm not sure what designers were thinking.  The front of your leg (your bony shin) is slimmer than the back of your leg (your meaty calf), so it only makes sense that showing more skin in front is more flattering.  When booties are higher in the front and lower in the back they're the opposite what's most flattering.  

6.  MOST FLATTERING LOOK:  Lower in the front and higher in the back, or even better, a slit down the front!  This creates that ultra-alluring vertical line.  You can't go wrong. 

Good luck!  Go get those booties!

Love,

Dylan