Cole Haan Laree stretch bootie
$280; Cole Haan
White Plains
Seven Dials Shelley boot
$59; Whim
Mount Kisco
Banana Republic tassel-zip booties
$178; Banana Republic
Mount Kisco
Kate Spade Dania boots
$548; Kate Spade
White Plains
Sorel Joan of Arctic wedge
$200; Love My Shoes
Bronxville; www.lovemyshoesco.com