In the past few years boots have made a fashionable comeback.  Once firmly relegated to the domain of fall and winter, boots are now showing up in all four seasons.  The variety of boots is verging on rivalling the variety of pumps.  There are tall boots, short boots, cut out boots, booties, flat boots, stiletto boots, over the knee boots – the list goes on and on.  Boots are by no means inexpensive.  A good pair can set you back a few hundred dollars.  So how do you choose which pair of boots is your best investment?

Start by assessing your fashion personality.  Do you wear high heels?  Do you follow the trends or opt for the classics? Is the majority of your day spent walking? Do you live in a geographical location with distinct climate changes or do you enjoy sun year around?  All these factors will impact which boot type is best for you.

Ladies that love high heels can wear any type of stiletto boot.  A closed toe, up-to-the-knee leather boot is great for locations that have cool fall and winter seasons.  This type of boot can be worn over jeggings or skinny jeans or under trousers and boot cut jeans.  They can even be worn under skirts that fall below the knee.  If your location is sunny and snow free come December, try a stiletto heeled boot with open toes or cut outs. 

Fashionistas that follow trends should aim for a boot that resembles the latest runway hit, but not the runway price tag.  High end fashion is extremely seasonal and if you don’t want to be out thousands of dollars for one pair of boots that are so-last-year by the next runway show, opt for copies or wait for a really good sale.

If your commute involves copious amounts of walking, there are several flat soled boots on the market that carry all the grace and elegance a stiletto heel.  Typically marketed as equestrian-style boots, this style of footwear can be worn in the same manner as stiletto heels: under or over the pants, under skirts, open or closed styles.

If tall boots are not your thing, consider booties.  These boots terminate at the ankle and are available in heeled, flat, open or closed.  Booties look best with jeans or trousers, but can also be worn with certain styles of skirts. Be cautious of your skirt length with booties; it is easy to look “stumpy” if your skirt is too long.  Always strive for a long, lean line when dressing your lower body. 

Not every woman is comfortable in or has the body type for jeggings or skinny jeans.  It is fine to wear other types of pants tucked into your boots as long as there is no bunching of fabric above the boot line and over the thighs. If you do not have a pair of pants suitable for tucking, try a pair of dark summer capri pants and boots. The shorter length shows off the boot and takes your capris from a summer wardrobe item to a year-round wardrobe staple.

Boots can go season to season and if cared for, can last for many years.  Boots make a wonderful addition to your wardrobe and add “mileage” to your closet. (Mileage is the ability of your clothes to transform for different looks and seasons.)  Although they can be pricey, a good sale or discount retailer (such as Payless Shoe Source) can provide a fashionable pair for under $100.00.  Assess your footwear situation.  If there is a lack of boots in your shoe closet, it is time to go shopping!