Free People Calgary Ankle Boot
1 / 10
Lightweight sundresses transition nicely from spring to summer with add-on accessories like a denim jacket and a pair of ankle boots. These cognac leather ankle boots fit the bill in distressed leather with an outer side zip.
Söfft Brighton Wedge Boots
2 / 10
A pair of lightweight over-the-knee boots, like this pair from Söfft Shoes, is the perfect addition to work-appropriate dresses. This pair is made from luxurious suede with intricate laser-cut details down the back of the leg and around the knee. A low wedge heel makes them comfortable for all-day wear.
Chinese Laundry Nostalgia Over-the-Knee Boots
3 / 10
These gray over-the-knee boots have an extra wide flared top, perfect for pulling over a pair of leggings or skinny jeans. Overlapping straps and a square buckle add detail to the flat-soled bottom.
Free People Carlene Ankle Boot
4 / 10
These tan leather boots with black patent leather inserts and black heels add a touch of polish to a pair of cuffed boyfriend jeans.
Ganni Tabitha Cowboy Ankle Boots
5 / 10
Sleek black suede puts an elegant spin on cowboy-style ankle boots. This low-heeled pair has pull-on loops on the sides and a softly rounded almond toe. Pair with a flirty skirt to toughen up the look.
London Rebel Lace-Up Flat Boot
6 / 10
Flat lace-up boots are comfortable and stylish when paired with leggings and an oversized sweater. This stacked-heel pair in a soft gray is the perfect choice for spring.
ASOS Artful Ankle Boots
7 / 10
Victorian details bring elegance to this pair of perfect-for-spring ankle boots. The nude heeled boots feature a floral lace section across the top and finely stitched lace-up ties.
Ganni Smilla Ankle Boot
8 / 10
Fringe details add a western vibe to everyday outfits. Try the trend in small doses on a pair of ankle boots. To rock the trend full-out, pair with a fringed purse as well.
Free People Daymoto Ankle Boot
9 / 10
Every woman needs a pair of chunky biker shoes that give her a rebellious feeling when paired with something as simple as a pair of dark jeans. These Free People ankle boots have an adjustable leather buckle and zip details that scream ‘attitude.’
ASOS Austin Ankle Boots
10 / 10
These gray-and-black heeled boots are as stylish as they are sturdy. The wooly gray body is accented with black leather toe and heel patches, and the soles are treaded for no-slip walking.