This is technically a boot but also functions as a sophisticated lace-up due to its streamlined welted outsole. No matter where you're living this time of year, you'll get a lot of wear out of a shoe like this. Dress it up with some nice navy-blue corduroys and a sturdy wool sweater.

Okay, these aren't new. I've personally owned a pair of these boots for the past decade and they're my go-to winter footwear. But the boot's laid-back look and weather-ready construction makes for a shoe that is always primed to be worn. Plus, the flexible Atlas Tred Polyurethane outsole can be resoled over and over again.

These pebbled leather boots are made to provide optimal comfort and support for the colder months. They're water-resistant and supported by a thick, yet surprisingly bouncy lug sole. Which means you can wear these well into spring.

There's something so elevated about a navy-colored sneaker. Nike stays true to their timeless track style with the retro swoosh and the original waffle sole. Pair these with some worn-in denim for a relaxed workday or your old collegiate sweats for weekend coffee runs.