The Classic: Riding Boots
The Real Deal
Once you break in these bona fide horse-riding boots, you’ll never want to take them off.
To buy: $380, ariat.com for stores.
These boots have cork midsoles, which contour to your feet.
To buy: $320, bedstu.com.
A rich mahogany color will pair well with everything from prints to solid black.
To buy: $190, nordstrom.com.
The Frye Company
The marbled leather of this sleek cut will age beautifully.
To buy: $348, thefryecompany.com.
Rubber-capped soles, as on these taupe pull-ons, keep you slip-free in slush.
To buy: $395, dkny.com for stores.
An angled cut and a buckle accent give this simple design extra panache.
To buy: $348, coach.com.
Aquatalia by Marvin K.
Elastic gussets accommodate full calves.
To buy: $398, Saks Fifth Avenue, 212-753-4000.
BE & D
Studs toughen up the buttery calfskin leather of these well-crafted boots.
To buy: $538, bluefly.com.
This lambskin leather pick has detachable ankle straps, giving you two looks in one.
To buy: Unfortunately, this product is no longer available.
Wear this chic over-the-knee style to give new life to leggings.
To buy: $329, musthaveshoes.com.