Boot season is well upon us. In fact, many gorgeous pairs are going on sale in advance of the holidays, so now is a great time to track down your ideal pair. Easier said than done? It's true that locating the perfect pair of boots can feel like an impossible task, even if what you're looking for seems incredibly basic or classic. If you're unsure what style would suit your style best or which features are more practical, it can feel even MORE overwhelming.
Here's a set of questions that could be used by just about ANY woman to locate her ideal pair of boots. If you're questing for a new pair this season, ask yourself:
- What's my preferred style? In my opinion, the shape of the boots shown above represents the tall-boot baseline. Those beauties are the Calvin Klein Selma boots,and they're a far cry from "fiscally conservative," but you can find similarly-shaped boots just about everywhere: Tall shaft, medium heel, solid color including the heel and sole, absolutely no detailing. Even if those boots look far too dull for your taste, it's best to begin with a very plain, sleek, pared-down design and THEN start adding embellishments like buckles, slouching, exposed zippers, etc. Build your perfect boot in your mind, then see if you can find something similar in the shops or online. Which neutral will I wear most? For most women, it's black. But cognac brown goes with EVERYTHING and generally looks more expensive. Also gray is fabulously flexible, and is becoming easier to find in all styles of boot.
- Is a heel practical? If you are on your feet all day then super-tall heels are right out, but can you deal with 1" or 2"? Are you better off with a flat/riding boot style? Or will these be boots that never walk more than five blocks at a time?
- Are your feet fussy? High or fallen arches? Bunions or corns? Need loads of support or flexible soles? Read customer reviews, check construction, ask questions, do everything you can to make sure that your potential new boots will caress and love your fussy feet. (Check Barking Dog Shoes' boot recommendations for some ideas.)
- Do I have fitting concerns? If you have wide or narrow calves, small or large feet, or any other traits that make boots tough to fit, you may prefer to shop in person. But if not, I highly recommend going online. I'd try scouring Endless

- , Zappos

- , and Amazon. The first two will allow you to refine your search and hunt down styles that you really love. Amazon makes the hunting harder, but has KILLER deals. If you find a style on Endless or Zappos, check Amazon to see if you can get a better deal.
- What's my budget? Multi-purpose boots can be bought cheap, but real leather and quality construction will last longer and be kinder to your feet. Still, never, ever spend more than you can truly afford.
Are you on the lookout for your ideal pair of boots? If so, do you think running through this checklist will be helpful in tracking them down? If you're already in possession of your perfect boots, how did you two find each other?
Sally McGraw is the author of Already Pretty, a daily blog about the intersection of style and body image.