If you need a good pair of winter boots, but aren't too fond of the bulk and weight typically associated with warmer footwear, you need a pair of Native Jimmy Duck Boots. They've taken the familiar silhouette of the duck boot and modernized it, building it with lightweight EVA material and updated colorways. Choose from jiffy black, regatta blue, torch red, and beaver brown. Each pair is completely waterproof, washable so they're easy to keep clean, anti-microbial and odor-resistant so you don't have to worry about them getting nasty, and lined with micro fleece for warmth on even the coldest days.
Keep your look on the track old-school, while still giving your feet all the comfort and protection of a modern boot, with these Sparco Classic Racing Shoes ($280). These shoes are made with a full leather upper, giving them a handsome retro look with a comfortable fit. The sole is still made to resist fuel and oil — just like any other FIA-approved shoe — while providing plenty of grip whether you're walking the pits or pushing the pedal down. The only challenge now will be finding a racing suit that still looks the part.