Awkward Holidays Pillows & Cushions

228 items

Buy any 2 and get 15% off.

I have awkward conversations around the holidays. Throw Pillow

Rachel the Artist

From $19.69

I have awkward conversations around the holidays. Throw Pillow

Rachel the Artist

From $19.69

I have awkward conversations around the holidays. Throw Pillow

Rachel the Artist

From $19.69

Funny Back to School Cartoon | Awkward Teacher and Student Meme Throw Pillow

MyxaART

From $19.85

Funny Jingle Bell Pug Christmas Portrait Throw Pillow

GenZFashion000

From $19.85

Not Safe for Family Functions Throw Pillow

StudioKuchiran

From $18.20

Not Built For This Dodo Meme | Cute Awkward Bird Relatable Sticker Design Throw Pillow

BabyStark

From $20.68

No Dignity Left - Funny Distressed Turkey Thanksgiving Humor Throw Pillow

OVXIO

From $19.85

Funny Relatable Holiday Chaos Family Dinner Sarcastic Meme Art Throw Pillow

SplashTastic

From $16.87

Vintage Distressed Misfits More Fun Toaster Cactus Shirt Throw Pillow

NovaDoodle Art Studio

From $17.37

Misfits Have More Fun – Cute Robot & Bunny Friends Illustration Throw Pillow

NovaDoodle Art Studio

From $17.37

Misfits Have More Fun – Cute Monster & Penguin Hug Illustration Throw Pillow

NovaDoodle Art Studio

From $17.37

Cute Monster & Penguin Hug Misfits Have More Fun Tee Throw Pillow

NovaDoodle Art Studio

From $17.37

Classic Cartoon Misfits Have More Fun Toaster Cactus Apparel Throw Pillow

NovaDoodle Art Studio

From $17.37

Anti Christmas Social Obligation 03 Throw Pillow

creativerooney

From $19.02

Anti Christmas Social Obligation 02 Throw Pillow

creativerooney

From $19.02

Anti Christmas Social Obligation 01 Throw Pillow

creativerooney

From $19.02

Gift Exchange Horror Stories – Satirical Holiday Cartoon with Creepy Characters Throw Pillow

SplashTastic

From $16.87

Holiday Survival Bingo 2025 – Dark Humor Family Drama Card Throw Pillow

SplashTastic

From $16.87

Band with Paper Bags on Heads Playing Music Around a Christmas Tree Throw Pillow

Naux | Design & Illustration

From $26.47

Funny 1 Percent Social Battery Introvert Throw Pillow

kreature56

From $23.15

Cringe Karaoke Frog | Funny Kawaii Christmas Singing Frog Throw Pillow

ColorSplash123

From $20.68

Forced Family Fun – Funny Sarcastic Quote Throw Pillow

TextMood

From $18.20

Social Battery: Holiday Edition (Critically Low) 2 – Cozy Introvert Christmas Humor Throw Pillow

PIXelayDesigns

From $21.51

I Tried to Be Festive – Funny Christmas Meme Design Throw Pillow

gavinroyal

From $18.20

I Came. I Saw. I Socially Shut Down – Holiday Introvert Humor, Male Character Throw Pillow

PIXelayDesigns

From $21.51

I Came. I Saw. I Socially Shut Down – Holiday Introvert Humor, Female Character Throw Pillow

PIXelayDesigns

From $21.51

I Came, I Saw, I Made It Awkward- Funny Christmas Throw Pillow

FitEnvy

From $19.85

Holiday Situationship – Awkward Season Energy Throw Pillow

Tattee

From $19.85

Forced Family Fun Retro Christmas Humor Design Throw Pillow

FreshVibe Prints

From $19.85

I Survived Another Family Gathering Throw Pillow

TheSimpleTee007

From $18.20

My Superpower? Surviving Christmas Dinner Holiday Humor Throw Pillow

AdyKurniawan

From $19.85

Unique Minimalist Pastel Christmas Meme Crew - Funny Pet Holiday Graphic Throw Pillow

Siamcatshop

From $19.85

Minimalist Pastel Christmas Meme Crew - Funny Siamese Cat & Friends Holiday Graphic Throw Pillow

Siamcatshop

From $19.85

Oh what fun. Throw Pillow

chestify

From $21.51

So jolly. Throw Pillow

chestify

From $21.51

Forced Family Fun Funny Holidays Emotional Damage Throw Pillow

HumansStuck12

From $24.81

Forced Family Fun Funny Holidays A Tradition of Chaos Throw Pillow

HumansStuck12

From $24.81

Forced Family Fun Funny Holidays The Annual Emotional Olympics Throw Pillow

HumansStuck12

From $24.81

Forced Family Fun Funny Holidays United in Dysfunction Throw Pillow

HumansStuck12

From $24.81

Forced Family Fun Funny Holidays Survival Mode Activated Funny Grinch Throw Pillow

HumansStuck12

From $24.81

Forced Family Fun Funny Holidays Maximum Chaos Throw Pillow

HumansStuck12

From $24.81

Awkward Holiday Axolotl – Cute Festive Anxiety Humor Throw Pillow

MadeByACJ

From $17.37

Funny Anxious Axolotl Gift – Relatable Christmas Cartoon Art Throw Pillow

MadeByACJ

From $17.37

It’s the Thought That Counts – Cute Nervous Axolotl Christmas Design Throw Pillow

MadeByACJ

From $17.37

So merry. Throw Pillow

chestify

From $21.51

Dear Santa, Let's Pretend You Didn't See That Throw Pillow

Gemty

From $18.20

So festive. Throw Pillow

chestify

From $21.51

Holiday Politics – Chaotic Christmas Dinner Cartoon Throw Pillow

ComedyInkFactor

From $18.20

National awkward moments day Throw Pillow

DreamOnShirts

From $18.20

National awkward moments day Throw Pillow

DreamOnShirts

From $18.20

National awkward moments day Throw Pillow

DreamOnShirts

From $18.20

Holiday Family Chaos Meme – Every Table Has the Same Characters Funny Quote Throw Pillow

aadventures

From $21.51

Holiday Family Drama Meme – Came for Cookies, Stayed for the Argument Throw Pillow

aadventures

From $21.51

Not Today Christmas Design | Sarcastic Introvert Holiday Humor Throw Pillow

The People’s Punchline

From $19.85

Ew People Christmas Design | Sarcastic Introvert Holiday Christmas Gift Throw Pillow

The People’s Punchline

From $19.85

Not Today Satan Christmas Design | Sarcastic Introvert Holiday Humor Throw Pillow

The People’s Punchline

From $19.85

Nope Christmas Design | Sarcastic Introvert Holiday Humor Throw Pillow

The People’s Punchline

From $19.85

Sorry I’m Late I Didn’t Want To Be Here | Sarcastic Christmas Introvert Humor Throw Pillow

The People’s Punchline

From $19.85

Side-Eye Santa Cat: Holiday Meltdown Throw Pillow

Feliciano3

From $18.20

Holiday Dinner Meme – Forks Freeze Mid-Bite Like Predator Documentary Throw Pillow

aadventures

From $21.51

Holiday Dinner Meme – The Sibling Look When Someone Says Something Unhinged Throw Pillow

aadventures

From $21.51

Holiday Dinner Politics Meme - When dessert becomes the battleground Throw Pillow

aadventures

From $21.51

Holiday Dinner Chaos Meme - A prayer for holiday survival - Fake News Funny Quote Throw Pillow

aadventures

From $21.51

Holiday Dinner Chaos Meme – Dog Leaves the Room When Vibes Get Weird Quote Throw Pillow

aadventures

From $21.51

Holiday Family Chaos Meme – Deviled Eggs Hostage Negotiator Funny Dinner Humor Throw Pillow

aadventures

From $21.51

Too Crumbly for Social Events. - Red Edition / Introvert Joke Funny T-Shirt Label Illustration Throw Pillow

introvertvibes

From $19.85

Too Crumbly for Social Events. / Introvert Joke Funny T-Shirt Label Illustration Throw Pillow

introvertvibes

From $19.85

Awkward Snowman Family Photo Throw Pillow

Napini

From $19.85

Season’s Greetings, Don’t Come Over. / Introvert Joke Funny T-Shirt Label Throw Pillow

introvertvibes

From $19.85

Introverting Around the Christmas Tree. / Introvert Joke Funny T-Shirt Label Throw Pillow

introvertvibes

From $19.85

Festive Possum, Funny Opossum Gift, Cute Holiday , Trash Animal Xmas, Awkward Possum Throw Pillow

disenokart

From $23.15

Festive Possum Christmas, Funny Opossum Gift, Cute Holiday , Trash Animal Xmas, Awkward Possum Throw Pillow

disenokart

From $23.15

Xmas ’84 – Funny Retro Crying Kid with Santa Vintage Christmas Design Throw Pillow

AddictiveDesign

From $19.85

I'm Just Here For The Holiday Cheer Don't Talk To Me Funny Christmas T-Shirt | Introvert Xmas Social Humor Throw Pillow

89BLACK

From $19.44

Mistle-Nope. Staying Home. / Introvert Joke Funny T-Shirt Label Throw Pillow

introvertvibes

From $19.85

Item preview, FriendsGiving Edition – And the Academy Award for MOST UNNECESSARY SIDE DISH CONTRIBUTION goes to... the friend who said “it’s a family recipe” like that made it better - V2 designed and sold by WheelieGdArt.

FriendsGiving Edition – And the Academy Award for MOST UNNECESSARY SIDE DISH CONTRIBUTION goes to... the friend who said “it’s a family recipe” like that made it better - V2 Throw Pillow

WheelieGdArt

From $19.85

FriendsGiving Edition – And the Academy Award for MOST UNNECESSARY SIDE DISH CONTRIBUTION goes to... the friend who said “it’s a family recipe” like that made it better Throw Pillow

WheelieGdArt

From $19.85

Item preview, FriendsGiving Edition – And the Academy Award for MOST UNHINGED RANT AT THE TABLE goes to... the friend whose rant was long, loud, totally out of nowhere — giving... Cheugy! - V2 designed and sold by WheelieGdArt.

FriendsGiving Edition – And the Academy Award for MOST UNHINGED RANT AT THE TABLE goes to... the friend whose rant was long, loud, totally out of nowhere — giving... Cheugy! - V2 Throw Pillow

WheelieGdArt

From $19.85

FriendsGiving Edition – And the Academy Award for MOST UNHINGED RANT AT THE TABLE goes to... the friend whose rant was long, loud, totally out of nowhere — giving... Cheugy! Throw Pillow

WheelieGdArt

From $19.85

Festively Avoiding People. / Introvert Joke Funny T-Shirt Label Throw Pillow

introvertvibes

From $19.85

FriendsGiving Edition – And the Academy Award for MOST UNHINGED RANT AT THE TABLE goes to... the friend whose rant was long, loud, totally out of nowhere — giving... Cheugy! Throw Pillow

WheelieGdArt

From $19.85

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Home & Living

Pillow

Awkward Holidays

Awkward Holidays artworks printed on 16”, 18”, 20”, 24”, 26”, 36” / 40 cm, 45 cm, 50 cm, 60 cm, 65 cm, 90 cm cushions for your lounge, bedroom, or dorm. The covers have hidden zipper closures, are printed front and back, and are totally washable.