Whether you pair it with slim jeans or with leggings, a chambray shirt is a casual-chic staple. Top it with a delicate necklace for the perfect menswear-goes-chic look.

Old Navy chambray shirt, $27; oldnavy.com

Spice up a jeans-and-tee routine with a cheerful patterned top. The henley is comfortable but the print is sophisticated, giving you the best of both worlds.

J. McLaughlin top, $135; jmclaughlin.com

Nothing can beat the soft texture of corduroys in the winter. Just pair them with your coziest sweater for an ideal weekend outfit.

Boden skinny cords, $59; bodenusa.com

With well-placed draping and trendy hemline, a striped skirt gets a fashionable makeover.

BCBGeneration, $98; bcbg.com

This style has more length in the back, making it ideal to pair with thick leggings, skinny jeans or even a skirt. Buy it for the versatility, wear it for the gorgeous dark blue shade.

Madewell tunic, $88; madewell.com

Brave the cold with a warm, peppy scarf. The cheerful stripes almost make twenty-below-zero temperatures seem bearable—the key word being almost.

Michael Kors scarf, $78; piperlime.com

You'll never be unprepared with a sturdy carry-all like this. The pretty leather trim is just a bonus.

Ralph Lauren, $298; ralphlauren.com

Go hands-free with an elegant cross-body bag. We can't say no to a classic...or to that deep, nut-brown leather.

J. McLaughlin messenger bag, $235; jmclaughlin.com

A military-inspired watch is an unexpected touch of menswear that we can't resist.

Timex watch, $50; piperlime.com

If you're heading out-of-town for the weekend, an suede, oxblood-colored weekend bag fits everything you need and keeps your style quotient high.

Cole Haan weekender, $498; endless.com

Don't let your hair fall flat just because you've clocked out: check out our 10 Easy Weekend Hairstyles.

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