Checkered Smiley Face Hats

Description: Checkered smiley face design made to make you smile.

Description: A fun and trendy design combining a classic smiley face with bold checkered patterns for a playful retro-inspired look. Perfect for teens, trendsetters, skaters, festival lovers, and anyone who enjoys cheerful aesthetic graphics. The vibe is upbeat, vintage-inspired, and full of positive energy.

Description: Illustration of Trippy Smiley Floral with Plaid Purple Pattern

Description: A pink retro smiley on a checkerboard background. Worry less, smile more – it is that simple.

Description: Smiley retro checkered artwork with a cheerful face and peace-sign hands. A playful smiley design for bright, upbeat everyday style.

Description: Celebrate big brother status with this stylish 'Cool Big Bro Club' retro typography design! Features 70s groovy bubble lettering framed by checkered borders, lightning bolts, and cheerful smiley faces. A fantastic announcement gift for newly promoted big brothers and pregnancy reveals.

Description: Groovy smiley face with peace signs and checkered pattern. Summer vibes!

Description: Turn up the cool factor with ultimate preppy Y2K rock-and-roll vibe! This trendy graphic features a yellow smiley face sticking its tongue out and throwing a peace sign, wearing an "X" eye alongside a black lightning bolt eye. Topped off with an off-white beanie covered in pink music notes, treble clefs, and beige stars, the character is flanked by bright pink checkered lightning bolts and playful paint splatters. Blending grunge, music aesthetics, and retro street style, this graphic is an excellent choice for music lovers, band members, festival-goers, teens, and fans of cool Y2K fashion. A fantastic birthday, holiday, or everyday gift for anyone who lives for good music and positive vibes!

Description: Kindergarten Vibes reads across the front of this design. The artwork features smiley face drawn in a retro style with yellow and pink tones, leaning into teacher. Made for kindergarten teacher and kindergarten student, and a natural pick for first day of school and teacher appreciation week.

Description: Volleyball Vibes Checkered Smiley Face Groovy Player

Description: Reading Rocks Checkered Smiley Face

Description: Floral Smiley Face Distressed

Description: Encourage empathy and cool confidence with this skater-inspired Choose Kindness Shirt featuring a sunglasses smiley face in a green cap against a classic checkerboard backdrop. Great for school spirit days, teachers, students, and positive everyday casual wear.

Description: Smiley face artwork in pink leopard, heart, and checkered patterns with stars, flowers, and lightning accents for a fun retro look.

Description: Smiley Face Checkered, Retro Leopard Smile, Happy Face, Boho Smiley, Trendy

Description: Celebrate game day with this fun, groovy design featuring a star-eyed smiley face on a checkered background. It is an ideal outfit for student athletes and teammates who love a colorful, retro sports aesthetic.

Description: In October we wear pink! Cute retro groovy smiley face wearing sunglasses with pink ribbons and checkered background. Perfect Breast Cancer Awareness Month gift for teachers, nurses, students, survivors, and family support squads.

Description: Celebrate big brother coolness with this rad 'Cool Big Bro Club' retro skateboard design! Features vintage groovy typography framed by orange checkered borders, lightning bolts, retro sunglasses smileys, and a classic skateboard deck. The ultimate pregnancy announcement gift for proud older brothers.

Description: Valentine Vibes artwork featuring a cute retro smile face wearing a heart patterned beanie, peace sign hands, red and pink checkered background, hearts, sparkles, and bold dotted lettering for Valentine’s Day, kids, women, teachers, friends, and groovy love season style.

Description: Spread good vibes and urban style with this bold 'Choose Kindness' streetwear design! Features a cheerful smiley face rocking a backward camo cap and flashing double peace signs against a distressed checkered pattern and camouflage block lettering. An awesome uplifting statement shirt for teens, teachers, and streetwear fans.

Description: Announce your big news in cool retro style with this Finally Big Brother design! Featuring a cool smiley face wearing sunglasses, a blue backwards baseball cap, and throwing peace signs in front of a black and white checkered grid with yellow sparkle stars. Perfect outfit for toddler boys, soon-to-be big brothers, pregnancy reveals, baby shower announcements, and family photos.

Description: "Fall Vibes." A trendy, retro 70s-inspired bubble typography design in rich burnt orange, mustard yellow, and forest green tones, complete with a classic smiley face, fallen maple leaves, and a groovy checkered base. A fun choice for retro lovers, back-to-school fall fashion, and cozy autumn style.

Description: Show your team spirit with this retro-inspired "Field Day Green Team" graphic. This groovy design is packed with fun Y2K and 70s nostalgia, featuring a cartoon peace sign hand, cheerful smiley faces, cute daisy flowers, and a bold checkered lightning bolt. Perfect for students, teachers, and parents wanting to match and support the green squad during school sports events, summer camps, or outdoor activity days. Stand out and win in style!

Description: Champion neurodiversity, inclusion, and sensory awareness with this retro 'Autism Acceptance' design! Features a vintage smiley face wearing noise-canceling headphones over a wavy checkered banner and the empowering mantra 'Advocate • Educate • Accommodate • Include'. A top-selling graphic for allies, educators, and therapists.

Description: Celebrate the school year with this groovy retro design featuring a happy smiley face with star eyes and colorful wavy text. Perfect for classroom energy.

Description: Celebrate neurodivergent comfort and sensory pride with this cheerful Autism Acceptance design! Highlights a bright yellow smiley face wearing noise-canceling headphones over a wavy retro checkerboard banner surrounded by the empowering words 'Advocate, Educate, Accommodate, Include.' The ultimate supportive graphic for allies and educators.

Description: Copyright of all these designs belongs to the artist (Meghan Wallace or Doodle by Meg LLC) and may not be reproduced by anyone other than the artist for sale or any other commercial use. In accordance with Intellectual Property Policies my designs have been created using my own process and personal references. With that said if you like my style, are interested in commission design work, or interested in licensing my work feel free to email or DM me!

Description: Gym vibes only! Retro groovy smiley face wearing barbell sunglasses with "Train Insane Or Remain The Same" slogan and checkered background. Perfect workout gift for gym lovers, bodybuilders, personal trainers, fitness enthusiasts, and weightlifters.

Description: Good vibes only! Stay positive and stay winning with this retro groovy Y2K pink smiley face featuring dollar sign sunglasses, rings, and checkered pattern background. Perfect streetwear motivation gift for teens, students, and positive vibe lovers.

Description: Upgrade your game day apparel with edgy retro vibes! Featuring bold typography spelling "Baseball Mom Like A Regular Mom But Cooler" alongside a lightning-eye baseball smiley face wearing a beanie and throw peace sign, this graphic is perfect for stylish, cool sports moms.

Description: Spread joy and hope with this fun checkered smiley face breast cancer awareness design. Perfect for breast cancer awareness month, honoring every cancer fighter, cancer survivor, and those who fight cancer. Featuring the pink ribbon to promote cancer support, health, and spread cancer awareness in style.

Description: Mental Health Matters Smiley

Description: Adventure awaits! Cool retro groovy smiley face with camping tents in sunglasses, pine trees, and compass icons. Perfect gift for hikers, campers, nature lovers, outdoor adventurers, and road trip enthusiasts.

Description: A retro-style design with bold, bubbly lettering reading "ANTI SOCIAL MOMS CLUB". Features pastel colors, smiley faces, small flowers, a butterfly, and starbursts. A black and white checkered border is at the bottom. The background is black.

Description: Beach vibes only! Pink retro groovy smiley face with ocean wave sunglasses, palm trees, and seashells, featuring "Salt Water Heals Everything" slogan. Perfect summer gift for beach lovers, ocean fans, surfers, tropical vacation trips, and Y2K aesthetic lovers.

Description: Coffee first! Neutral vintage retro groovy smiley face wearing coffee mug sunglasses and holding a hot coffee cup with "But First Coffee Then Conquer" slogan. Perfect aesthetic gift for coffee lovers, baristas, teachers, office workers, and morning coffee fans.