Deborah Lewis’s Cayman Bag is stylish and more functional than the average handbag because it has a discrete umbrella pocket on the side, which makes it the ideal spring bag if you live somewhere with unpredictable spring weather. At least, it’s discrete until an umbrella is tucked inside it. The bag is made of leather and is accented with nickel hardware. There interior is nylon and has multiple pockets for phone, keys and wallet. There are three colors to choose from: kelly green, midnight black or chocolate brown. The umbrellas are available separately. Price: $438.