The tall slouchy boot, reminiscent of bold 80's era fashion, made its debut last year in the fall of 2019 and is sure to be all over our feeds yet again in 2020. With a relaxed yet voluminous feel of material gathered at the ankles, this boot is the chicest boot you'll slide into this cold-weather season. Paired with both a faux leather blazer and nude skirt topped with an all-white tube top for a not so casual first dinner date night look.

As charming as other boot styles may be, nothing compares to a python-embossed stiletto boot to complete your fall must-haves. Animal print is always a go-to when searching for the perfect winter boots, however, snakeskin is the latest trend in exotic prints. These electrifying bold yellow calf boots make all of my shoe dreams come true, including the not so high heel that makes them easier to wear all day long. Wearing a subtle pinstripe blazer jacket and high-waist leather shorts, this is a super chic outfit choice for a transitional summer-to-fall look.

The chunky platform sole is slowly stomping its way back into our lives while becoming one of the biggest boot trends on the rise for fall/winter 2020. Dr. Martens classic lace-up boots are one of a kind and known by many generations for its grunge aesthetic and youthful counterculture fashion appeal. With the ability to adapt to almost every outfit when paired, these boots are a staple for the cold weather months and will never go out of style. I wore my high-rise platform Doc Martens with a two-toned one-piece knit romper as well as a yellow blazer for a modern-yet-90s take on this chunky boot style.