Boss and Boss's Day Gifts - A Custom Caricature

Unique and Personalized Artwork Makes the Best of All Boss's Day Gifts! Celebrate a great boss or mentor with a gift that is sure to be the hit of the office! It's fast and easy to commission our talented artists to hand draw a fully custom Boss's Day or Boss caricature based on your photos and ideas. Some opt for a caricature that captures the whole team including the boss, taking the enjoyment and laughter to a whole new level.

caricature of a female boss cracking a whip, in a black frame with signed mat


Caricatures Make the Best Boss Gifts:
A caricature is one of the very few gifts that can capture your boss's personality:

  • Likeness
  • Occupation
  • Interests
  • Even quirky habits

Don't forget our optional custom framing including engraved plaques and signable mats to add to the personalized appeal of this unique gift for your boss.


From $104


Caricature Features

  • Hand drawn - fully custom!
  • USA artists & support!
  • Proof to review & approve!
  • Satisfaction guaranteed!
  • Frames, engraved plaques, sign-able mats!

Boss Caricature Examples

Below you will see boss caricature examples that we've done for others. It's a great way to get ideas, see our quality, and get a good laugh! Remember, your Boss's Day caricature is 100% custom but if you happen to want one like one of our examples, right click, save it, and upload it with your photos.

  • The most popular request for boss caricatures

    Caricature gift of boss with feet up on his desk
  • Boss in his/her office surrounded by a couple of their
    favorite items, striking a boss-like pose

    Boss on the phone in her office
  • Boss caricatured with his dogs

    Unique gift of a caricature of a boss and his dogs dressed like ninjas
  • Doctor in front of his specialized machinery
  • Boss on the phone surrounded by a sea of folders
  • Send us a picture of their actual office and our
    artist can create a caricatured version for their artwork

    Doctor in his office with golf and fishing items
  • funny Wizard of Oz themed caricature with boss dressed as witch
  • A fun way to incorporate golf into the boss' gift

    boss practicing his putts in his office
  • Group gift for the boss

    A group of coworkers celebrating their awesome boss around a conference table
  • a boss with multiple arms as she multitasks like a pro
  • Has your boss always wanted to play for their favorite
    sports team? Our artist can make it happen!

    boss winding up to throw a baseball from a pitchers mound
  • Our favorite gifts for the boss are ones that shows
    the boss's personality and adds a twist of humor.
    Truly a gift they'll be talking about for years!

    boss standing in a dungeon with a sign that says Compliance Department
  • Texan police officer at the shooting range
  • Great gift for a boss who travels a lot

    gift for a boss that travels a lot shows her in the airport with her laptop
  • Personalize your gift to the recipient

    boss with his feet up and reading a newspaper
  • Bosses often wear many hats

    boss wearing many hats as she mediates in her office chair
  • doctor holding his stethoscope and gesturing toward the viewer
  • Give us a picture of their pet and our artist can
    include the pet as a 2nd subject

    boss holding a glass of red wine as she rides her magical flying pug
  • group of five bosses in front of a blue backdrop
  • military boss giving orders to his subordinates
  • female boss enjoying a meal outdoors
  • unique boss gift of him in Lakers uniform and dunking basketball
  • caricature of a boss in her office with papers flying
  • dentist pulling his lab coat apart to reveal Superman logo underneath
  • gift for a boss in his unique purple office
  • female orthodontist in exam room with comic cat Garfield in brand new braces
  • caricature of a man fishing in the mountains
  • group of four men and one woman hanging out on a golf course as a group gift for their boss
Customer Reviews

4.9 out of 5(12142 reviews)

Latest Customer Reviews

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by Fredericksburg , VA

5 stars

"Another satisfying experience using your services! There’s no better gift for those who don’t want for much and this is always extremely appreciated! Thank you! "

by San Jose, CA

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by Lexington, MA

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