What: Blue pinstripe shirtdress

Where: The Gap (various locations)

Price Tag: $68

Why: There's something inherently sexy about a woman wearing a man's dress shirt. Check out the Gap's version of this classic look, a belted shirtdress in blue pinstripe. Give thanks to Coco Chanel, who introduced menswear-inspired clothing for women back in the '20s. Aside from the comfort and ease of wearing them, shirtdresses are a great staple to build your look on. The pinstripes and cuffed sleeves mean business, but there are a number of other ways to wear this dress. Pair it with vintage cowboy boots and roll up the sleeves for an afternoon stroll, or add leggings and ankle boots for the fall. The self-tie belt is charming, but a colourful cinch would step the look up. This is the kind of garment you can throw on and feel great in; forget the old adage–business and pleasure do mix. The dress is also available in black, white, and navy.