BB Dakota Sweater
This chunky wool-blend pullover is decadently soft—a nice perk, considering the price.
To buy: $47, 877-747-3754.
Land's End Canvas Shirt
Thin cotton with a broken-in, worn-it-forever feel.
To buy: $60, canvas.landsend.com.
With only 1 percent spandex, this pair provides a bit more figure-skimming structure than most skinny jeans.
To buy: $22, aeropostale.com.
Karen London Bracelet
A studded wooden bead on a colorful cord is simple yet surprising.
To buy: $75, karenlondon.com.
Rubber-soled faux-leather boots are ready for urban or countryside treks.
To buy: $99, zappos.com.