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Preppy fashion knows no bounds in Penguin’s hands.

Classic polo fits, button-front shirts, and blazers show off the liveliest incarnations of plaid and check.

For over 50 years, the Penguin icon has stood as an Original. Now it’s your turn to stand as an original. Throw on some Penguin and hit the street or the links.


Quick View Original Penguin Leonard L/S Shirt in Navy Original Penguin Leonard L/S Shirt in Navy Original Penguin Leonard L/S Shirt in Navy $99.00

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Original Penguin Leonard L/S Shirt in Navy

Original Penguin Leonard L/S Shirt in Navy

$99.00

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Get the best of both worlds with this flannel button down from Original Penguin. Cut for a classic fit, this top features a jaspe twill flannel weave that enhances the overall color so you can enjoy your flannel without channeling your inner lumberjack. But even if you are in the mood to move, the stretch fabric will effortlessly form with your body to keep you worry and hassle free. Throw it on with your favourite khakis and black loafers.

Also available in store at Roadtrip.

99% Cotton, 1% Elastane

Machine Wash Cold


Quick View Original Penguin Liam L/S Shirt in Coal Original Penguin Liam L/S Shirt in Coal Original Penguin Liam L/S Shirt in Coal $99.00

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Original Penguin Liam L/S Shirt in Coal

Original Penguin Liam L/S Shirt in Coal

$99.00

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Slip into this staple shirt from Original Penguin and see for yourself how easy it is to stay comfortable and on trend effortlessly. Featuring a soft stretch cotton fabrication, this top moves with you while still having you look your freshest thanks to the slim heritage fit. With the iconic logo embellished chest pocket and sharp collar neckline, this is the perfect shirt to go from the office to drinks with the guys.

Also available in store at Roadtrip.

98% Cotton, 2% Elastane

Machine Wash Cold


Quick View Original Penguin Benjamin Polo in Navy Original Penguin Benjamin Polo in Navy Original Penguin Benjamin Polo in Navy $79.00

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Original Penguin Benjamin Polo in Navy

Original Penguin Benjamin Polo in Navy

$79.00

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A cut above the rest! Original Penguin brings us your next go-to standout polo. Crafted from a soft cotton material, this piece features a pique fabrication and multi-tone striped details along the collar. With a button lined placket, colour block accents on the sleeves and tailored slim fit, this is the perfect piece to rock for your next date night.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


Quick View Original Penguin Ryan Reversible in Ash Original Penguin Ryan Reversible in Ash Original Penguin Ryan Reversible in Ash $79.00

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Original Penguin Ryan Reversible in Ash

Original Penguin Ryan Reversible in Ash

$79.00

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Get two looks in one with this stylish reversible shirt from Original Penguin. Made from a breathable cotton jersey fabric, this crewneck is built for a classic heritage fit to keep you comfortable and cozy all day long. Polished off with the signature Penguin logo, pair this top with a denim jacket and brown loafers for a great night on the town look.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

60% Cotton, 40% Polyester

Machine Wash Cold


Quick View Original Penguin Ryan Reversible in Navy Original Penguin Ryan Reversible in Navy Original Penguin Ryan Reversible in Navy $79.00

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Original Penguin Ryan Reversible in Navy

Original Penguin Ryan Reversible in Navy

$79.00

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Get two looks in one with this stylish reversible shirt from Original Penguin. Made from a breathable cotton jersey fabric, this crewneck is built for a classic heritage fit to keep you comfortable and cozy all day long. Polished off with the signature Penguin logo, pair this top with a denim jacket and brown loafers for a great night on the town look.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

60% Cotton, 40% Polyester

Machine Wash Cold


Quick View Original Penguin Henry Henley in Grey Original Penguin Henry Henley in Grey Original Penguin Henry Henley in Grey $89.00

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Original Penguin Henry Henley in Grey

Original Penguin Henry Henley in Grey

$89.00

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Great for kicking up your feet at home or relaxing with friends and family, this henley style shirt from Original Penguin is your new cozy day compadre. Built from 100% Cotton, this soft henley is cut for a slim fit with traditional crewneck neckline and button lined placket. Pair with a khaki jogger and your favourite runners.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


Quick View Original Penguin William Polo in Navy Original Penguin William Polo in Navy Original Penguin William Polo in Navy $65.00

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Original Penguin William Polo in Navy

Original Penguin William Polo in Navy

$65.00

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Your favourite old school classic gets a revamp in this timeless polo from Original Penguin. Featuring a pique fabrication for added texture, this polo is crafted from 100% ultra soft cotton to bring you a more comfortable and breathable experience. The slim fit and dark hue creates a more flattering and tailored look. Pair with olive-toned joggers and sleek black runners.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


Quick View Original Penguin William Polo in Black Original Penguin William Polo in Black Original Penguin William Polo in Black $65.00

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Original Penguin William Polo in Black

Original Penguin William Polo in Black

$65.00

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Your favourite old school classic gets a revamp in this timeless polo from Original Penguin. Featuring a pique fabrication for added texture, this polo is crafted from 100% ultra soft cotton to bring you a more comfortable and breathable experience. The slim fit and dark hue creates a more flattering and tailored look. Pair with olive-toned joggers and sleek black runners.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


Quick View Original Penguin Paul L/S Plaid in Red Original Penguin Paul L/S Plaid in Red Original Penguin Paul L/S Plaid in Red $99.00

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Original Penguin Paul L/S Plaid in Red

Original Penguin Paul L/S Plaid in Red

$99.00

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Original Penguin takes your favourite weekend staple and adds a modern twist to bring you a button down you'll find yourself reaching for again and again! This flannel shirt comes packed with a twisted yarn fabrication creating a more striking and vivid colour variation throughout the shirt. Cut for a relaxed fit, this piece is accompanied by a collared neckline, button lined placket and chest pocket. Polish off this look with some blue denim and white converse.

Also available in store at Roadtrip.

60% Cotton, 40% Polyester

Machine Wash Cold


Quick View Original Penguin Peter L/S Plaid in Blue Original Penguin Peter L/S Plaid in Blue Original Penguin Peter L/S Plaid in Blue $99.00

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Original Penguin Peter L/S Plaid in Blue

Original Penguin Peter L/S Plaid in Blue

$99.00

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It's true, no one can resist the clean cut or classic style of a great plaid shirt, especially one crafted by Original Penguin. This lightweight and soft flannel shirt is built for a classic fit and made from 100% cotton to ensure that this piece will be your wardrobe buddy for a long time! Pair with some dark wash denim and boat shoes for effortless style.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


Quick View Original Penguin Brian Polo in Blue Original Penguin Brian Polo in Blue Original Penguin Brian Polo in Blue $75.00

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Original Penguin Brian Polo in Blue

Original Penguin Brian Polo in Blue

$75.00

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Conventional is boring, but tradition is timeless! Channel classic polo style with a modern twist in this standout piece from Original Penguin. Built for a tailored slim fit, this shirt comes packed with a chest pocket featuring the signature logo and has contrast details along the placket, sleeve cuffs and collar to really make this a must-have piece. Toss on your favourite chinos and white converse sneakers for the perfect laid back look.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


Quick View Original Penguin Footprint Tee in Navy Original Penguin Footprint Tee in Navy Original Penguin Footprint Tee in Navy $49.00

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Original Penguin Footprint Tee in Navy

Original Penguin Footprint Tee in Navy

$49.00

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A man can never have to many graphic tees and this one from Original Penguin is the perfect addition! Cut for a slim fit, this tee is crafted from an ultra soft jersey fabrication to ensure your top moves with you and keeps up with your busy day. Hit the mark every time and pair with some light wash denim and your favourite zip-up.

Also available in store at Roadtrip.

50% Polyester, 37% Cotton, 13% Rayon

Machine Wash Cold


Quick View Original Penguin Timothy L/S in Noir Original Penguin Timothy L/S in Noir Original Penguin Timothy L/S in Noir $89.00

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Original Penguin Timothy L/S in Noir

Original Penguin Timothy L/S in Noir

$89.00

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Comfort has never looked so good! This long sleeve from Original Penguin is crafted from their signature ultra soft cotton blend to keep you comfortable and effortlessly in style. The slim fit cut is the perfect tailored look to take you from your day on the town to drinks with the guys!

Also available in store at Roadtrip.

60% Cotton, 40% Polyester

Machine Wash Cold


Quick View Original Penguin Simon Sweater in Navy Original Penguin Simon Sweater in Navy Original Penguin Simon Sweater in Navy $89.00

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Original Penguin Simon Sweater in Navy

Original Penguin Simon Sweater in Navy

$89.00

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Built to keep you cozy and comfortable, this piece is crafted from 100% soft lambswool to keep you warm on breezy days. Cut for a classic crewneck style with ribbed cuffs and hemline, we love this piece paired with some blue denim and your favourite runners.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

100% Lambswool

Machine Wash Cold


Quick View Original Penguin Simon Sweater in Ocean Original Penguin Simon Sweater in Ocean Original Penguin Simon Sweater in Ocean $89.00

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Original Penguin Simon Sweater in Ocean

Original Penguin Simon Sweater in Ocean

$89.00

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Built to keep you cozy and comfortable, this piece is crafted from 100% soft lambswool to keep you warm on breezy days. Cut for a classic crewneck style with ribbed cuffs and hemline, we love this piece paired with some blue denim and your favourite runners.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

100% Lambswool

Machine Wash Cold


Quick View Original Penguin Lincoln L/S Shirt in Blue Original Penguin Lincoln L/S Shirt in Blue Original Penguin Lincoln L/S Shirt in Blue $99.00

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Original Penguin Lincoln L/S Shirt in Blue

Original Penguin Lincoln L/S Shirt in Blue

$99.00

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Classic and crisp is the name of the game with this signature button down from Original Penguin. Crafted with a soft and lightweight cotton material, this piece is built with a collared neckline and button lined placket. The subtle dotted pattern throughout really elevates this basic piece to the next level! Tuck into a black pant for a great 9-5 look.

Also available in store at Roadtrip.

60% Cotton, 40% Polyester

Machine Wash Cold


Quick View Original Penguin Aaron L/S Shirt in Green Original Penguin Aaron L/S Shirt in Green Original Penguin Aaron L/S Shirt in Green $99.00

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Original Penguin Aaron L/S Shirt in Green

Original Penguin Aaron L/S Shirt in Green

$99.00

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One button down to rule them all! Perfect for on and off the clock looks alike, this gingham shirt stands above the rest. Cut for a slim heritage fit, this piece is crafted from a lightweight twill fabrication to keep your look crisp and cool. Polished off with a button lined placket, collared neckline and chest pocket with signature Original Penguin crest, we love this top paired with black denim and a brown loafer.

Also available in store at Roadtrip.

99% Cotton, 1% Polyester

Machine Wash Cold


Quick View Original Penguin Jaxon Crewneck in Blue Original Penguin Jaxon Crewneck in Blue Original Penguin Jaxon Crewneck in Blue $89.00

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Original Penguin Jaxon Crewneck in Blue

Original Penguin Jaxon Crewneck in Blue

$89.00

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Perfect for layering and some laid back Sunday vibes, this versatile piece is certainly a must-have! Crafted from a soft cotton blend, this top is built for a slim fit to bring you a more tailored look. The duel knit fabrication joins together two layers of fabric to bring you extra comfort while the waffle pattern creates square ridges that boosts absorbency and airflow throughout the top. Polish this look off with a puffy vest and dark wash denim.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

60% Cotton, 40% Polyester

Machine Wash Cold


Quick View Original Penguin Jaxon Crewneck in Green Original Penguin Jaxon Crewneck in Green Original Penguin Jaxon Crewneck in Green $89.00

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Original Penguin Jaxon Crewneck in Green

Original Penguin Jaxon Crewneck in Green

$89.00

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Perfect for layering and some laid back Sunday vibes, this versatile piece is certainly a must-have! Crafted from a soft cotton blend, this top is built for a slim fit to bring you a more tailored look. The duel knit fabrication joins together two layers of fabric to bring you extra comfort while the waffle pattern creates square ridges that boosts absorbency and airflow throughout the top. Polish this look off with a puffy vest and dark wash denim.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

60% Cotton, 40% Polyester

Machine Wash Cold


Quick View Original Penguin Jaxon Crewneck in Red Original Penguin Jaxon Crewneck in Red Original Penguin Jaxon Crewneck in Red $89.00

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Original Penguin Jaxon Crewneck in Red

Original Penguin Jaxon Crewneck in Red

$89.00

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Perfect for layering and some laid back Sunday vibes, this versatile piece is certainly a must-have! Crafted from a soft cotton blend, this top is built for a slim fit to bring you a more tailored look. The duel knit fabrication joins together two layers of fabric to bring you extra comfort while the waffle pattern creates square ridges that boosts absorbency and airflow throughout the top. Polish this look off with a puffy vest and dark wash denim.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

60% Cotton, 40% Polyester

Machine Wash Cold


Quick View Original Penguin Jaxon Crewneck in Grey Original Penguin Jaxon Crewneck in Grey Original Penguin Jaxon Crewneck in Grey $89.00

Added to Your Tote!

Original Penguin Jaxon Crewneck in Grey

Original Penguin Jaxon Crewneck in Grey

$89.00

View all product details

Perfect for layering and some laid back Sunday vibes, this versatile piece is certainly a must-have! Crafted from a soft cotton blend, this top is built for a slim fit to bring you a more tailored look. The duel knit fabrication joins together two layers of fabric to bring you extra comfort while the waffle pattern creates square ridges that boosts absorbency and airflow throughout the top. Polish this look off with a puffy vest and dark wash denim.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

60% Cotton, 40% Polyester

Machine Wash Cold


Quick View Original Penguin Thomas Sweater in Blue Original Penguin Thomas Sweater in Blue Original Penguin Thomas Sweater in Blue $89.00

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Original Penguin Thomas Sweater in Blue

Original Penguin Thomas Sweater in Blue

$89.00

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Crafted from super soft 100% cotton, this is the new staple long sleeve you've been seeking. Featuring a signature popcorn knit to create a unique and enticing texture throughout, this sweater is cut for a classic crewneck style with ribbed cuffs and hem. Pair with some dark wash denim and loafers for a casual cool day vibe.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


Quick View Original Penguin Arlo Polo in Navy Original Penguin Arlo Polo in Navy Original Penguin Arlo Polo in Navy $79.00

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Original Penguin Arlo Polo in Navy

Original Penguin Arlo Polo in Navy

$79.00

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A sure winner, Original Penguin has created your next short sleeve go-to! This pique fabrication polo features distinctive outlines along the placket, sleeves and collar and crafted from a breezy linen blend for a comfortable slim fit finish. The neutral colour allows for the perfect opportunity to pair this look with those unique printed shorts you've been waiting to wear. With the signature Penguin logo, finish this style with boat shoes and your favourite shades to be patio ready.

This style is also available in Other Colors.

Also available in store at Roadtrip.

Heritage Slim Fit

55% Linen, 45% Cotton

Machine Washable


Quick View Original Penguin Murphy L/S Shirt in Mint Original Penguin Murphy L/S Shirt in Mint Original Penguin Murphy L/S Shirt in Mint $99.00

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Original Penguin Murphy L/S Shirt in Mint

Original Penguin Murphy L/S Shirt in Mint

$99.00

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Look distinguished in this sleek shirt from Penguin. Made from 100% cotton, the Oxford fabrication is crafted with a braided weave that stands the test of time for a look that's classic and durable. Cut slim for a sharp fit, this buttoned collar piece is finished with the famous Penguin logo embroidery at the chest. A super versatile shirt, it looks just as great with a clean trouser at the office as it does with navy shorts and boat shoes.

This Style from Original Penguin is also available in Other Colors.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Murphy L/S Shirt in Cloud Original Penguin Murphy L/S Shirt in Cloud Original Penguin Murphy L/S Shirt in Cloud $99.00

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Original Penguin Murphy L/S Shirt in Cloud

Original Penguin Murphy L/S Shirt in Cloud

$99.00

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Look distinguished in this sleek shirt from Penguin. Made from 100% cotton, the Oxford fabrication is crafted with a braided weave that stands the test of time for a look that's classic and durable. Cut slim for a sharp fit, this buttoned collar piece is finished with the famous Penguin logo embroidery at the chest. A super versatile shirt, it looks just as great with a clean trouser at the office as it does with navy shorts and boat shoes.

This Style from Original Penguin is also available in Other Colors.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Victor Windbreaker in Black Original Penguin Victor Windbreaker in Black Original Penguin Victor Windbreaker in Black $135.00

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Original Penguin Victor Windbreaker in Black

Original Penguin Victor Windbreaker in Black

$135.00

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Cheat the wind in this sleek jacket from Penguin. As versatile as it is functional, this black windbreaker features a stand collar, full zip, side slit pockets, and of course, the iconic logo embroidery at the chest. Whether you're throwing it on for a run or pairing it with jeans and white sneaks for weekend activities, you'll look great and the wind won't know what hit it!

Also available in store at Roadtrip.

100% Nylon

Machine Washable


Quick View Original Penguin Hillview Polo in Red Original Penguin Hillview Polo in Red Original Penguin Hillview Polo in Red $68.00

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Original Penguin Hillview Polo in Red

Original Penguin Hillview Polo in Red

$68.00

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You’ll keep cool in this 100% cotton top that features contrasting colour on the placket to add a stylish detail. The pique knit gives this polo a subtle textured feel to the touch. We love this piece paired with your favourite chinos and converse for a classic preppy vibe.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Jackson Henley in Navy Original Penguin Jackson Henley in Navy Original Penguin Jackson Henley in Navy $79.00

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Original Penguin Jackson Henley in Navy

Original Penguin Jackson Henley in Navy

$79.00

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This henley from Original Penguin is classic yet modern thanks to its timeless stripe design, henley collar, and three-button closure. Crafted from 100% cotton, it's both lightweight and breathable, and the heritage slim fit keeps your look sleek, making it perfect for layering.

This Style from Original Penguin is also available in Other Colors.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Maddox Shorts in Navy Original Penguin Maddox Shorts in Navy Original Penguin Maddox Shorts in Navy $62.00$89.00

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Original Penguin Maddox Shorts in Navy

Original Penguin Maddox Shorts in Navy

$62.00$89.00

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Original Penguin makes finding warm weather staples effortless with these slim fit shorts. Crafted from a soft and lightweight cotton material, flat back welt pockets and finished with a dobby fabrication these shorts are perfect for the man on the go. The neutral navy colour allows for versatility when looking for bottoms to pair with your awesome print and button down tops. Or keep this look casual with a white tee and sandals for a relaxed Sunday vibe.

Also available in store at Roadtrip.

Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Gemini Block Short in Khaki Original Penguin Gemini Block Short in Khaki Original Penguin Gemini Block Short in Khaki $53.00$89.00

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Original Penguin Gemini Block Short in Khaki

Original Penguin Gemini Block Short in Khaki

$53.00$89.00

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Shake up your shorts repertoire with this colour block pair from Penguin. The angled colour contrast design keeps things fresh and modern! These shorts are crafted in a slim fit and are kept flexible thanks to a stretch-cotton fabrication. Slip 'em on with a white tee and fresh sneaks.

These Shorts from Original Penguin are also available in Other Colors.

Also available in store at Roadtrip.

Slim Fit

98% Cotton, 2% Elastane

Machine Washable

Inseam: 8"


Quick View Original Penguin Nauti Shorts in Navy Original Penguin Nauti Shorts in Navy Original Penguin Nauti Shorts in Navy $62.00$89.00

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Original Penguin Nauti Shorts in Navy

Original Penguin Nauti Shorts in Navy

$62.00$89.00

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Get nautical with these striped shorts from Penguin. Cut for a slim fit, they're crafted from a lightweight cotton to keep you cool on the hottest of days. You're sure to be a fan of the mini stripe design and dobby fabrication. Throw them on with a white tee or navy long sleeve and white sneaks for a coastal look.

Also available in store at Roadtrip.

Slim Fit

100% Cotton

Machine Washable

Inseam: 8"


Quick View Original Penguin Original Hoodie in Grey Original Penguin Original Hoodie in Grey Original Penguin Original Hoodie in Grey $65.00$108.00

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Original Penguin Original Hoodie in Grey

Original Penguin Original Hoodie in Grey

$65.00$108.00

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This pullover sweater by Penguin is made from 100% cotton and features a French terry fabrication. A slim fit and hooded collar make this piece perfect for everyday. Pair with joggers to look comfy-casual.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Page: 12

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This is just a sampling of amazing items that we carry and love. We get new arrivals in our physical shop daily.


Roadtrip is your destination for today’s top brands and best indie designers

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Canada K1N 1K2
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613.562.0992