As we move into the -ber months, it becomes more acceptable to swap those summer sandals for full-coverage boots. We’ve selected five classic styles every woman should not be without, and break down the right and wrong ways to style them.


A Brit-inspired shoe that’s loved by both guys and girls, the Chelsea boot is characterized by elastic panels on both sides and a pull tab at the back. It may make sense to tuck your skinnies into your Chelsea boots, but this method is a quick way to emphasize shapely or muscular calves (not everyone’s blessed with lean model-like legs, after all!). Instead, wear cropped or cuffed jeans that fall just above the top of your boots. It’s just as effortless yet decidedly cooler.


When the occasion calls for something sleek and polished, a bootie or shoe boot is the way to go. In a perfect world, it should have a leg-lengthening stiletto heel, and comes in either a luxurious material or is finished by statement embellishments. Don’t fall into the trap of making the bootie look sleazy and cheap by pairing it with bandage dresses and revealing club wear. Instead, make it work for the office with a soft blouse tucked into a structured pencil or A-line skirt, or a tuxedo vest and slim cropped trousers.


The biker boot is the footwear equivalent of the leather biker jacket. It’s tough and not to be messed with. While you’d love to wear yours with just about everything, do leave them out of the office as they don’t exactly scream "workwear." Instead, add edge to casual, girly dresses by grounding them with a buckled, badass pair. You also can’t go wrong with every model off duty’s favorite outfit: a cool piece of outerwear (parka, blazer, the choice is yours), an easy tee, and skinny jeans (tucked, always!).


Granted, a lot of boots can be categorized as ankle boots. What we have in mind, however, has a low, chunky heel for easy walking; comes in a neutral black or brown; and is completely devoid of any fussy details—except, perhaps a simple zip or a buckle or two. Have a strict dress code at work? You might have to think twice before wearing this. But when it comes to casual wear, anything goes! It’s so versatile, you can wear it with dresses, mini skirts, jeans, and tailored shorts.


Torrential downpours make the rubber rain boot a commuting necessity, as stomping through puddles runs the risk of ruining your shoes. Save them for the outdoors and only when it’s actually raining—wear them indoors and you just end up looking ridiculous. On the flipside, unlike other shoes, you don’t always have to stick to conventional colors and prints. Classics like navy and army green always work; but for some color and cheer, you can also opt for yellow, red, purple, and quirky patterns.

PHOTOS: Pixabay, Nordstrom

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