Boot shopping is supposed to be fun, but generally it's a huge pain in the butt.  All of the stores carry the same merchandise, the souls are too slippery, heels are too high, the calves are too thin, or there are just too many buckles, bells and whistles.  That's before you even get to looking at the price tag. 

With all of the winter sales, this is the perfect time to find that elusive pair of boots to take you through the winter and well into next fall.  The best way to find what you are looking for is to extend your search online so you can either buy them there or find a store that carries them locally.

So what should you look for?

1. Over the knee riding boots are very popular right now.  The trick to differentiate between classy and, er, Lady of the Night, is to keep the heel low.  Tuck them into jeans or wear them with thick stockings and a skirt.  Rowr!! 

We like these Via Spiga Brook Boots.

Grey made a welcome appearance this fall in handbags, boots and jackets.  It's a nice alternative to brown or black if you can find the right shade. 

These soft leather boots from Chinese Laundry are a great casual look at a silly good price.

Another colour that has made a comeback is this:

You might be tempted to call it medium brown, orangey brown or not quite beige, but most stores are calling it cognac, which sounds much more sophisticated than orangey-brown. 

This style of boot is best for spring or fall since it looks smashing with jeans and an over-sized sweater or sweater dress, but not so much with a long black winter coat. 

We love this style, but be warned that when buying boots without a side zipper, you'll need at least a 1/2 size larger just to be able to get your foot in.  Personal experience here.    Oooh! I want those!


We saved the best for last.  These beauties are Frye, a high quality legendary brand that builds their boots to last.  They are pricier but these are not one season wonders.  You will be wearing these boots again long after they have gone out and come back into style.  The rounded toe shape is classic, the thicker heel won't wear down to the nail and they had the foresight to add a side zip.  Oh, and we like the buckles too.

All boots are available on Endless.com, which is also where we, um, borrowed the boot pictures from.

Where did you find your perfect boots?