Katie Holmes's Chicest Street Style Looks

Holmes made an uncharacteristically bold style choice on Monday when she attended a holiday party in an off-the-shoulder black leather Ralph Lauren jacket ($2,990; ralphlauren.com), matching trousers, a camel coat grazing her shoulders, and classic black pumps.

Katie bundled up in a plaid scarf and a pine green coat, worn over a pair of straight-leg jeans and dark brown boots as she stepped out in N.Y.C.

Holmes stepped out in N.Y.C. in a long suede coat (shop a similar look here), a patterned dress, slouchy mahogany boots, and a matching shoulder bag. 

Holmes stepped out to run errands in a cozy knee-length pink coat with three oversize decorative buttons down the front. Along with the statement coat, she donned a beige wide-brim hat, blue jeans, and light ballet flats. 

Holmes headed out for dinner in N.Y.C.'s West Village on Sunday in a floral plum-hued kimono, frayed hem jeans (shop a similar pair here), a classic white tee, a leather handbag by Tod's, and a pair of triple band sandals with golden buckles. 

Holmes was spotted on the set of The Gift in Montreal wearing relaxed skinny jeans, beige flats (shop a similar style here), and a black zip-up sweater, an on-trend fanny pack clinging to her waist.

The actress was spotted out and about in the Big Apple looking casual-cool in denim-on-denim. Holmes artfully paired her Tribeca Film Festival hoodie with a collared shirt, jean jacket, and straight-leg pants, which she accessorized with mirrored sunnies and white Converse sneakers.

Fresh off a relaxing vacay, Holmes bundled up on the streets of N.Y.C. in a navy blue coat (shop a similar look here), long relaxed-fit blue jeans, and white Converse sneakers (shop a similar style here), accessorizing with a pair of tinted cat-eye sunglasses and a large black bucket bag (shop a similar look here). 

Collar popped and photo ready, the stylish mom stunned in a navy and burnt sienna checked jacket, faded jeans, and her trusty Gucci loafers ($630; www.nordstrom.com), pulling it all together with an ivory handbag (shop a similar style here). 

Holmes was barely recognizable at the airport in a floppy tan hat and sunglasses, but her chic street style set her apart from the crowd. Dressed in a cropped beige jacket, distressed jeans, and classic Gucci loafers ($630; www.nordstrom.com), the actress proved her sartorial know-how. 

The chicest mom out there arrived at an event in N.Y.C. wearing a white peasant blouse, two-tone cropped jeans (shop a similar look here), and a pair of leather Gucci booties ($1,290; net-a-porter.com).

The Dawson's Creek alum braved the N.Y.C. winter in a plaid mini dress, a double-breasted wool coat (shop a similar coat here), thin tights, and a set of black booties (shop a similar pair here). 

Holmes made a case for spring style in October, stepping out in a mid-calf length polka dot skirt (shop a similar look here), a navy blue ribbed tee, black pumps with pearl-laden heels, and a quilted Chanel shoulder bag (shop a similar look here). 

The trend-setting actress went autumnal in N.Y.C., wearing a red leather miniskirt (shop a similar look here), a ribbed crewneck sweater, and a mustard-colored peacoat. 

The Kennedys actress stunned in Chanel high-waisted floral trousers (shop a similar look here) and a simple black blouse.