Retirement Sleep Masks
Funny, cute and slightly sarcastic sleep masks for retirement. 26 designs
Birthday (212)
Christmas (53)
Bride & Bachelorette (31)
Graduation (13)
Holidays (56)
Retirement Joke Sleep Mask: I'm Retired Have Fun At WorkRetirement$12.95
Under New Management Sleep Mask for Retired HusbandsRetirement$12.95
Retirement Humor Sleep Mask: I Don't Have To, I'm RetiredRetirement$12.95
Retired Life Sleep Mask Doing What I Want When I WantRetirement$12.95
Retired Mondays Sleep Mask: Happy on Mondays Then You're RetiredRetirement$12.95
Retired Legend Sleep Mask: The Legend Has Retired DesignRetirement$12.95
Retired Man Sleep Mask: See Wife For Details DesignRetirement$12.95
Retirement Plan Sleep Mask: My Retirement Plan Find Bigfoot DesignRetirement$12.95
Retirement Freedom Sleep Mask: Do What I Want When I Want DesignRetirement$12.95
Retired Humor Sleep Mask: Does This Make Me Look Retired? DesignRetirement$12.95
Retired Have Fun Sleep Mask: A Playful Retirement GiftRetirement$12.95
Divorce Humor Sleep Mask: Happily Ever After, I'm Outta Here DesignRetirement$12.95
Retired Queen Sleep Mask: The Queen Has Officially Retired DesignRetirement$12.95
Retired Woman Sleep Mask: This Chick Is Retired DesignRetirement$12.95
Retired Guy Sleep Mask - This Guy Is Retired DesignRetirement$12.95
Teacher Retirement Sleep Mask: School Is Out ForeverRetirement$12.95
Retired Happy Hour Sleep Mask: It's 5 O'Clock Everywhere DesignRetirement$12.95
Air Force Retirement Sleep Mask: An Air Force Legend HasRetirement$12.95
Retired Emo Fan Sleep Mask: Nostalgic Text Design for Music LoversRetirement$12.95
Retired Teacher Sleep Mask: School's Out Forever DesignRetirement$12.95
Pro Papa Sleep Mask: Retired Dad Grandkids GiftRetirement$12.95
Retirement Cruising Plan Sleep MaskRetirement$12.95
Retired I Worked Sleep Mask - Funny Retirement Design for MenRetirement$12.95
Retired Firefighter Sleep Mask: Retired But FirefighterRetirement$12.95
Retirement Gift Sleep Mask: The Myth, The Legend Has Retired DesignRetirement$12.95
Retired Not Working Sleep Mask: I'm Retired, You're Not DesignRetirement$12.95What you’ll find here
Retirement Sleep Masks are a playful way to mark the moment someone finally clocks out for good. Whether you are shopping for a coworker, a parent, or a friend who has earned a long nap, these designs bring a little humor to the big milestone. Browse the collection and you will find Air Force Retirement for a proud service member, Retired Papa Professional for the grandfather who has perfected the art of doing nothing, and Retirement Princess for anyone ready to be treated like royalty.
Who they’re for
Some designs lean into the joy of freedom. Retiree Freedom sums up the feeling of finally having your days back, while Retiree Happy Mondays gives a cheeky nod to the fact that every day now feels like the weekend. If your favorite retiree has been dreaming of skipping the morning alarm, Retirement Excuse is a lighthearted pick that makes the point for them.
Gift ideas
Retirement Sleep Masks make a fun gift, a keepsake for a farewell party, or a silly addition to a retirement card. Choose the design that best fits the personality of the person you are celebrating and enjoy a few more laughs along the way.
Will one mask fit everyone?
One size fits most heads, with an adjustable elastic strap.
Can I personalize a design?
No — every NapWink design is ready-made, so what you see is what you get.
How fast is shipping?
Most orders arrive in 5–10 business days within the US. Shipping is $4.95, free over $35.