The Best Gifts for Bosses

  • To Gift or Not to Gift?

    While family members and close friends are the mainstays on most Christmas shopping lists, there is one person many people aren’t so sure they should include: their boss. The ambivalence stems from the fact that there really is no hard or fast rule on whether you should give a gift to your direct superior. “It really depends on the corporate culture at your office,” says Rusty Rueff, career and workplace expert for Some companies may even have rules regarding holiday gift giving, so you should check with Human Resources before spending money on a present. “You should also consult with other employees, because you don’t want to be the only one,” says Dana Holmes, who runs the recommendation site Photo Credit: Getty Images
    Boss Gifting 101
  • Boss Gifting 101

    If you do decide your relationship with your boss warrants a little holiday cheer, you’ll want to keep it simple… and fairly generic. “Gifts should not be personal,” says Bruce Hurwitz, president of Hurwitz Strategic Staffing in New York.  “[It] should not have any romantic overtures (such as chocolates or flowers) and should not be embarrassing in any way.” It also shouldn’t be very expensive. Holmes suggests keeping your boss budget between $25 and $100. Where the monetary value falls on that scale will depend on how close you are or how closely you work with your boss Finally, Rueff advises employees to make sure they are gifting for the right reasons. “Your motives are a lot more transparent than you imagine,” he says. “Bosses know who is being genuine and who isn’t.” MainStreet rounded up some of the gifts you can get that are thoughtful without being pricey or inappropriate. Photo Credit:  Getty Images
    Coffee Mugs 2.0
  • Coffee Mugs 2.0

    If your boss is reliant on morning coffee, chances are four or five other co-workers will also be giving them a wrapped mug at the end of December. But there are ways to keep this old reliable from being too bland. Employees can green-gift this reusable version of the paper morning coffee cup, which retails for $15 on, or give a subtle nod to multitasking with this $18 face mug that doubles as a cookie jar at Then there’s the Spink from Spoon Sisters (pictured) which actually suctions to a desk and holds your bosses’ favorite coffee cup, water bottle or soda can in place. The product, which costs $19.95, is designed to protect your desk and important paperwork from potential spillage. Photo Credit:
    Desktop Adornments
  • Desktop Adornments

    Gifts to brighten up cubicles are also always a good idea, especially since a decorated cube can help ease office stress. Desktop terrariums are a popular product over at Etsy, which sells three of the potted plants for $18 or a singular plant pod for $11. Another cool paperweight is this $35 Cubebot Puzzle (pictured), a suggestion from that is made of paper and rubber bands and transforms from a cube to, well, a robot. Photo Credit:
    Chilly Jilly
  • Chilly Jilly

    If your boss is always complaining that they are cold, you might want to get them a Chilly Jilly. These wrinkle-resistant shawls, which come in a silk bag, can be kept in an office desk and pulled out whenever the office air conditioning gets a little wacky. The wraps, suggested by, cost $35 each. Photo Credit:
    Shoe Bag
  • Shoe Bag

    Similarly, if your boss has a long commute or likes to wear his or her sneakers to and from work, you can consider giving them this travel shoe bag designed to protect dress shoes from the wear and tear of being carted to and from work or shoved in a desk drawer. In addition to a gentleman’s shoe bag (pictured), which retails for $13.95, Spoon Sisters sells an embroidered high heel bag for $18.95. Photo Credit:
    Tech Accessories
  • Tech Accessories

    If your boss is into gadgets or always tethered to his or her Blackberry or iPad, you may want to give them a tech accessory. Etsy has several cool  iPad cases that range between $6 and $120. FredFlare also has a particularly cool case that makes an iPad look like an old-school Etch-a-Sketch (pictured) that retails for $42. Photo Credit:
    Work Less, Play More Notepad
  • Work Less, Play More Notepad

    This notepad from Spoon Sisters (pictured) is a cool gift idea, especially if your boss is a sports fan, since it makes an everyday office item more interesting. (The underside of each piece of paper is patterned to look like a different sports ball, perfect for shooing into the nearby wastebasket.) The notepad retails for $8.95. also suggests this Desktop Dodgeball set from UncommonGoods, which retails for $9.75. Photo Credit:  Spoon Sisters
    Hootch Owl
  • Hootch Owl

    You might remember that substituting wine with wine accessories is one way to make a boring gift more interesting. If your boss is a wine connoisseur, you might want to give them this Hootch Owl (pictured) from Red Envelope, a new take on vintage wine openers that retails for $49.95. also suggests giving a wine sampler from The Tasting Room, such as this assortment of Mario Batali’s favorites for $32.99. If your boss is more into beer, you might want to go with this $49.95 six-glass set from Red Envelope. Each glass is styled to enhance aroma and taste of certain craft beers. Photo Credit: Red Envelope
    Group Gift
  • Group Gift

    Holmes says employees can also consider getting together and buying one big gift for their boss, like a one-on-one golf lesson with a PGA pro (available from Cloud 9 Living for $129) or even a Kindle. MainStreet also recommends this Ballpark pen from Red Envelope (pictured), which retails for $189.95. The pen’s high price is due to the fact that it’s made of authentic wood from seats in old ball parks, including Yankee Stadium, Wrigley Field, Fenway Park, Dodger Stadium and Busch Stadium. Photo Credit: Red Envelope
    10 Awesome TV Infomercial Gifts
  • 10 Awesome TV Infomercial Gifts

    If you’re also looking for some gift suggestions for your family and friends, check out MainStreet’s roundup of these 10 awesome TV infomercial gifts! (We’re big fans of the Forever Lazy here at MainStreet!) Photo Credit: joelk
    Join us on Facebook
  • Join us on Facebook

    Join the MainStreet team and other readers on our lively Facebook page! Discuss our newest stories and get links to breaking content, automatically. Click here to add us. Photo Credit: lawtonchiles
Show Comments