Silhouettes Boot

SADDLE UP
This cotton canvas and leather equestrian boot makes the ankle look slimmer.

Silhouettes, $129; Silhouettes.com
J.Crew boots

FREE RANGE
A larger calf can get right into this timeless knee-high.

J.Crew, $345; JCrew.com
Lumiani boots

LADY IN RED
There's space to spare in a riding-boot-style pull-on.

Lumiani, $179; Zappos.com
Tashkent by Cheyenne boot

STRETCH CLASS
The hand-knit shaft expands to fit any calf.

Tashkent by Cheyenne, $738; BareFoottess.com
Sam Edelman boots

GOING UP
This over-the-knee boot makes wide calves a nonissue.

Sam Edelman, $175; The New York Look, NYC; 212-382-2760
Rockport boot

COMFORT: CIRCLE GAME
Round buckles shine on a roomy boot from the comfort-shoe people.

Rockport, $200; Rockport.com
RSVP Boots

Stripe Out
A patent tuxedo stripe takes these from work-a-day to out-all-night.

RSVP "Chery," RSVP, $149; Zappos.com
Hunter boot

Godess of the Hunt(ess)
Iconic wellies fit much more than skinny jeans.

"Huntress," Hunter, $115; Zappos.com

O Boot Guide
O's Complete Boot Guide:
More than 70 styles we love

From the November 2009 issue of O, The Oprah Magazine