Funny Trucker Hats

Show off your personality with our Funny Trucker Hat Collection! From sarcastic sayings and dog lover favorites to everyday humor and good vibes, these boutique trucker hats are perfect for making people smile wherever you go.
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  • Woman wearing Dog Mother Wine Lover Trucker Hat with distressed black front and gray mesh back showing white embroidered Dog Mother Wine Lover lettering with gray pullover and golden retriever backdrop
    Sale

    Dog Mother Wine Lover Trucker Hat

    Dog Mother Wine Lover Trucker Hat
    $20.00
    $20.00 $30.00
  • Woman wearing Good Vibes Only Trucker Hat with pink front and pink mesh back showing retro Good Vibes Only lettering with smiley face daisy flowers with white tank and outdoor floral backdrop
    Sale

    Good Vibes Only Trucker Hat

    Good Vibes Only Trucker Hat
    $20.00
    $20.00 $30.00
  • Woman wearing Here for the Snacks Trucker Hat with white front and white mesh back showing pink and hot pink embroidered Here for the Snacks lettering with black outline with pink sweatshirt and outdoor porch backdrop
    Sale

    Here for the Snacks Trucker Hat - White

    Here for the Snacks Trucker Hat - White
    $20.00
    $20.00 $30.00
  • Woman wearing Good Vibes Trucker Hat with white front and hot pink bill and mesh back tilted down showing multicolor Good Vibes embroidery with smiley face detail and Good Days Ahead chalkboard backdrop
    Sale

    Good Vibes Trucker Hat - Pink

    Good Vibes Trucker Hat - Pink
    $20.00
    $20.00 $30.00
  • Woman wearing Electric Smiley Trucker Hat with white front, hot pink bill, and blue lightning-eye smiley patch with denim jacket and Good Vibes and Tan Lines neon sign backdrop
    Sale

    Electric Smiley Trucker Hat

    Electric Smiley Trucker Hat
    $20.00
    $20.00 $30.00
  • Woman wearing distressed black Here for the Snacks trucker hat with tan mesh back at baseball game
    Sale

    Here for the Snacks Trucker Hat

    Here for the Snacks Trucker Hat
    $20.00
    $20.00 $30.00
  • A woman on a wooden boardwalk at the beach wearing a black and gray trucker hat with the text 'BEACH HAIR Don't Care' and a white tunic top, holding brown sandals.
    Sale

    Beach Hair Don't Care Trucker Hat

    Beach Hair Don't Care Trucker Hat
    $20.00
    $20.00 $30.00
  • A woman wearing a distressed black trucker-style baseball cap with white text that reads 'WORKOUT HAIR DON'T CARE'. The cap has a washed black denim-look front panel and a gray mesh back.
    Sale

    Workout Hair Don't Care Trucker Hat

    Workout Hair Don't Care Trucker Hat
    $20.00
    $20.00 $30.00
  • A woman at a petting zoo wearing a black and gray trucker hat with the text 'LLAMA HAIR don't CARE' and a llama graphic, posing with a llama in the background.
    Sale

    Llama Hair Don't Care Trucker Hat

    Llama Hair Don't Care Trucker Hat
    $20.00
    $20.00 $30.00
  • A woman at a fair rides a merry-go-round wearing a pastel tie-dye cap with a teal smiley face, a cream "Good Vibes" t-shirt, and denim shorts, holding pink cotton candy.
    Sale

    Tie-Dye Smiley Face Cap

    Tie-Dye Smiley Face Cap
    $20.00
    $20.00 $30.00
  • A smiling woman rides in the passenger seat of a convertible along a coastal highway wearing a white Passenger Princess Trucker Hat with light blue embroidery and rope accent.
    Sale

    Passenger Princess Trucker Hat

    Passenger Princess Trucker Hat
    $20.00
    $20.00 $30.00
  • A woman wearing a black trucker hat with the text 'I'm only talking to my dog today.' stands outdoors by a lake with a golden retriever dog beside her, holding a travel mug.
    Sale

    I’m Only Talking to My Dog Today Trucker Hat

    I’m Only Talking to My Dog Today Trucker Hat
    $20.00
    $20.00 $30.00
  • A woman on a rooftop patio at sunset wearing a dusty rose and beige trucker hat with 'I'll Bring the Bad Decisions' embroidered text, smiling and holding a drink with a city skyline in the background.
    Sale

    I’ll Bring the Bad Decisions Trucker Hat

    I’ll Bring the Bad Decisions Trucker Hat
    $20.00
    $20.00 $30.00
  • A woman walking two dogs on a paved path in a park, wearing a gray zip-up hoodie, black leggings, and a black trucker hat that reads "Pawsitive Vibes Only."
    Sale

    Pawsitive Vibes Only Trucker Hat

    Pawsitive Vibes Only Trucker Hat
    $20.00
    $20.00 $30.00
  • A woman sitting in a cozy armchair with two cats, wearing a black trucker hat with the text 'CAT MOTHER wine lover' in white. She is holding a glass of red wine in a warm, decorated living room setting.
    Sale

    Cat Mother Wine Lover Trucker Hat

    Cat Mother Wine Lover Trucker Hat
    $20.00
    $20.00 $30.00
  • A man at an outdoor bar wearing a cream and red baseball cap that reads "Put It On My Ex-Girlfriend's Tab," holding a burger and pointing to the brim, with a beer in the foreground.
    Sale

    Put It On My Ex-Girlfriend's Tab Baseball Cap

    Put It On My Ex-Girlfriend's Tab Baseball Cap
    $20.00
    $20.00 $30.00
  • A woman wearing a distressed trucker-style baseball cap with 'ADULT-ISH' printed in white on a dark gray washed front panel and mesh back. She is holding the brim of the hat, posing in a styled indoor setting with a rustic sign and plants in the background.
    Sale

    Adult-ish Trucker Hat

    Adult-ish Trucker Hat
    $20.00
    $20.00 $30.00
  • A woman wearing a black and gray trucker-style baseball cap with the text 'I'LL BRING the GANGSTA RAP' in white, teal, and pink lettering. The photo is taken outdoors on a city street with blurred storefronts and plants in the background.
    Sale

    I'll Bring the Gangsta Rap Trucker Hat

    I'll Bring the Gangsta Rap Trucker Hat
    $20.00
    $20.00 $30.00