Boots are a personal decision. They tend to be investment pieces that you plan on wearing every time winter rolls around and you're forced to contend with trudging through the snow to get to your car or haul yourself to the subway. Given the amount you'll pull your boots on during the colder months, it's important that you get this decision right.

There's certainly room to have more than one pair in your arsenal—lock down a durable pair of snow boots that you'll wear after a storm blows through your area, but also maybe have a solid Chelsea boot or cap-toe boot for an option that you can wear to work or out to dinner that will still protect your feet from the cold.

Right before winter truly kicks off is a great time to start thinking about your winter boot plan and, luckily for you

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