A Shoulder and Crossbody Bag: Kate Spade Kailee Medium Flap Shoulder Bag This Kate Spade Kailee Medium Flap Shoulder Bag ($119, originally $379) is a great option because it can be worn as both a crossbody and a shoulder bag. Also, the front flap helps your belongings stay more secure. Image Source: surprise.katespade.com Kate Spade Kailee Medium Flap Shoulder Bag $119 from surprise.katespade.com Buy Now