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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 Original Hoodie in Grey Original Penguin Original Hoodie in Grey Original Penguin Original Hoodie in Grey $108.00

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Original Penguin Original Hoodie in Grey

Original Penguin Original Hoodie in Grey

$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


Quick View Original Penguin Miguel S/S Shirt in White Original Penguin Miguel S/S Shirt in White Original Penguin Miguel S/S Shirt in White $88.00

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Original Penguin Miguel S/S Shirt in White

Original Penguin Miguel S/S Shirt in White

$88.00

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No one will be able to 'leaf' you alone in this button down by Penguin. With its slim fit and short sleeves, it is the perfect shirt to dress up or down. Made from 100% cotton, you'll be comfortable but still stylish in this leaf print. Pair with your favourite pair of chinos or denim.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Original Crew in Navy Original Penguin Original Crew in Navy Original Penguin Original Crew in Navy $98.00

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Original Penguin Original Crew in Navy

Original Penguin Original Crew in Navy

$98.00

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Everyone definitely needs this versatile crewneck sweater in their wardrobe. Made from a French terry in 100% cotton, this unique fabrication is a looped marled yarn that creates a soft textured finish. Pair with a collared shirt underneath and some converse to give this sweater a preppy look.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

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 Kenzo Polo in Hunter Original Penguin Kenzo Polo in Hunter Original Penguin Kenzo Polo in Hunter $69.00

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Original Penguin Kenzo Polo in Hunter

Original Penguin Kenzo Polo in Hunter

$69.00

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Classic with a unique twist! Made from 100% cotton, it features a slim fit and a pique knit fabrication. The white piping on this top adds a special detail. Pair with black jeans and black lace up boots to add a pop of color to your outfit.

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 Jackson Henley in Black/White Original Penguin Jackson Henley in Black/White Original Penguin Jackson Henley in Black/White $79.00

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Original Penguin Jackson Henley in Black/White

Original Penguin Jackson Henley in Black/White

$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 Jeffrey L/S Shirt in Navy Original Penguin Jeffrey L/S Shirt in Navy Original Penguin Jeffrey L/S Shirt in Navy $89.00

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Original Penguin Jeffrey L/S Shirt in Navy

Original Penguin Jeffrey L/S Shirt in Navy

$89.00

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Plaid never gets old, and this design from Penguin has caught our eye. Crafted from soft cotton, this checkered shirt is cut with a slim fit for a sleek tailored look, and features a mini collar as well as the famous Penguin logo embroidered on the chest pocket.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Jarred L/S Shirt in Grey Original Penguin Jarred L/S Shirt in Grey Original Penguin Jarred L/S Shirt in Grey $99.00

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Original Penguin Jarred L/S Shirt in Grey

Original Penguin Jarred L/S Shirt in Grey

$99.00

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Throw on something a little different than your usual go-to's and button-up into this awesome paint-like splatter print shirt. Cut for a slim fit from 100% Cotton, it has a super soft handle for a feel that's as comfy as it is sleek. A subtle Penguin logo embroidery dons the chest pocket.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Quintin L/S Tee in Wine Original Penguin Quintin L/S Tee in Wine Original Penguin Quintin L/S Tee in Wine $79.00

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Original Penguin Quintin L/S Tee in Wine

Original Penguin Quintin L/S Tee in Wine

$79.00

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Stripe it up in this comfortable long sleeve tee from Original Penguin. Crafted from 100% cotton, the jersey crew neck is cut with a slim fit for a sleek and sharp look. You'll love the chest pocket embroidered with a subtle Penguin logo.

This Style from Penguin is also available in Other Colors.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Quintin L/S Tee in Navy Original Penguin Quintin L/S Tee in Navy Original Penguin Quintin L/S Tee in Navy $79.00

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Original Penguin Quintin L/S Tee in Navy

Original Penguin Quintin L/S Tee in Navy

$79.00

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Stripe it up in this comfortable long sleeve tee from Original Penguin. Crafted from 100% cotton, the jersey crew neck is cut with a slim fit for a sleek and sharp look. You'll love the chest pocket embroidered with a subtlre Penguin logo.

This Style from Penguin is also available in Other Colors.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Darron Sweatshirt in Navy Original Penguin Darron Sweatshirt in Navy Original Penguin Darron Sweatshirt in Navy $79.00

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Original Penguin Darron Sweatshirt in Navy

Original Penguin Darron Sweatshirt in Navy

$79.00

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Build your casual wardrobe with this comfortable long sleeve tee. Its 100% cotton French terry fabrication makes it ultra soft and the crew neck offers classic comfort. This slim fit piece is finished with the renowned Penguin logo embroidered at the chest.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Trystan Hoodie in Navy Original Penguin Trystan Hoodie in Navy Original Penguin Trystan Hoodie in Navy $108.00

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Original Penguin Trystan Hoodie in Navy

Original Penguin Trystan Hoodie in Navy

$108.00

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Getting dressed is easy with this drop shoulder hoodie. Classic in fit and design, it features a front zip and pockets. Crafted from 100% cotton for a soft feel, it's subtly finished with a subtle Penguin logo embroidery at the chest.

Also available in store at Roadtrip.

Classic Fit

100% Cotton

Machine Washable


Quick View Original Penguin Cohen Plaid L/S Shirt in White Original Penguin Cohen Plaid L/S Shirt in White Original Penguin Cohen Plaid L/S Shirt in White $69.00$98.00

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Original Penguin Cohen Plaid L/S Shirt in White

Original Penguin Cohen Plaid L/S Shirt in White

$69.00$98.00

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We are loving this plaid by Penguin as the perfect addition to your wardrobe. Made from 100% cotton, it features a slim fit and a plain weave fabrication. Pair with black jeans and leather boots for the perfect date night look.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Diesel L/S Shirt in Coal Original Penguin Diesel L/S Shirt in Coal Original Penguin Diesel L/S Shirt in Coal $59.00$88.00

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Original Penguin Diesel L/S Shirt in Coal

Original Penguin Diesel L/S Shirt in Coal

$59.00$88.00

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This henley by Penguin features a soft cotton blend and 3 button closure. A slim fit keeps you sleek yet comfortable for everyday wear. This slubbed fabric has slight knots on the surface to create a hint of texture and a two-toned look. Pair with sneakers and joggers for a laid-back look.

Also available in store at Roadtrip.

Heritage Slim Fit

65% Cotton, 35% Polyester

Machine Washable


Quick View Original Penguin Marshawn L/S Shirt in Red Original Penguin Marshawn L/S Shirt in Red Original Penguin Marshawn L/S Shirt in Red $62.00$89.00

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Original Penguin Marshawn L/S Shirt in Red

Original Penguin Marshawn L/S Shirt in Red

$62.00$89.00

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Add dimension to your button-down repertoire thanks to this shirt with a dobby fabrication. Crafted from lightweight cotton in a slim fit, it features a mini dot gingham design, mini collar, and the iconic Penguin logo embroidered on the chest pocket.

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 Marshawn L/S Shirt in Moss Original Penguin Marshawn L/S Shirt in Moss Original Penguin Marshawn L/S Shirt in Moss $62.00$89.00

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Original Penguin Marshawn L/S Shirt in Moss

Original Penguin Marshawn L/S Shirt in Moss

$62.00$89.00

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Add dimension to your button-down repertoire thanks to this shirt with a dobby fabrication. Crafted from lightweight cotton in a slim fit, it features a mini dot gingham design, mini collar, and the iconic Penguin logo embroidered on the chest pocket.

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 Landon Plaid L/S Shirt in Red Original Penguin Landon Plaid L/S Shirt in Red Original Penguin Landon Plaid L/S Shirt in Red $62.00$89.00

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Original Penguin Landon Plaid L/S Shirt in Red

Original Penguin Landon Plaid L/S Shirt in Red

$62.00$89.00

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Just what you need in your wardrobe, this casual plaid shirt from Penguin is crafted from pure cotton and cut for a sleek, slim fit. Classic features include a mini collar, button-down placket and Penguin logo embroidery at the chest pocket.

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 Landon Plaid L/S Shirt in Navy Original Penguin Landon Plaid L/S Shirt in Navy Original Penguin Landon Plaid L/S Shirt in Navy $62.00$89.00

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Original Penguin Landon Plaid L/S Shirt in Navy

Original Penguin Landon Plaid L/S Shirt in Navy

$62.00$89.00

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Just what you need in your wardrobe, this casual plaid shirt from Penguin is crafted from pure cotton and cut for a sleek, slim fit. Classic features include a mini collar, button-down placket and Penguin logo embroidery at the chest pocket.

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 Bertram L/S Shirt in Grape Original Penguin Bertram L/S Shirt in Grape Original Penguin Bertram L/S Shirt in Grape $49.00$99.00

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Original Penguin Bertram L/S Shirt in Grape

Original Penguin Bertram L/S Shirt in Grape

$49.00$99.00

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The deep purple hue will be a great addition to your wardrobe, it looks especially great when you roll up the cuffs to reveal a pop of gingham. The slim fit is kept comfortable thanks to its cotton fabric with natural stretch. Crafted with a full button-down placket and mini collar, it's finished with a subtle Penguin logo embroidery at the chest.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Delmer L/S Shirt Navy Original Penguin Delmer L/S Shirt Navy Original Penguin Delmer L/S Shirt Navy $69.00$99.00

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Original Penguin Delmer L/S Shirt Navy

Original Penguin Delmer L/S Shirt Navy

$69.00$99.00

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This navy slim fit oxford shirt gets a modern update with a handsome geo print. Crafted from 100% cotton, this button-down mini collar shirt has natural stretch so you can move and be comfortable. The chest pocket is finished with a subtle Penguin logo embroidery.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Milo L/S Shirt in Grape Original Penguin Milo L/S Shirt in Grape Original Penguin Milo L/S Shirt in Grape $69.00$99.00

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Original Penguin Milo L/S Shirt in Grape

Original Penguin Milo L/S Shirt in Grape

$69.00$99.00

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As dapper as it is classic, this gingham shirt comes in a handsome plum hue with a mini collar and button-down placket. The heritage slim fit keeps you looking sharp and mechanical stretch cotton gives you all the comfort and mobility you need. The chest pocket is finished with a subtle Penguin logo embroidery.

Also available in store at Roadtrip.

Heritage Slim Fit

98% Cotton, 2% Elastane

Machine Washable


Quick View Original Penguin Brenton Flannel L/S in Plum Original Penguin Brenton Flannel L/S in Plum Original Penguin Brenton Flannel L/S in Plum $59.00$99.00

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Original Penguin Brenton Flannel L/S in Plum

Original Penguin Brenton Flannel L/S in Plum

$59.00$99.00

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This is one of our best flannel shirts yet! Unbelievably soft, it's cut for a slim fit and features handsome hues of plum, wine, and navy for an unparalleled plaid. Crafted from 100% cotton, the twisted yarn fabrication provides a distinct alternating texture to add that extra element of style. The chest pocket is finished with a subtle Penguin logo embroidery.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Tyron L/S Shirt in Blue Original Penguin Tyron L/S Shirt in Blue Original Penguin Tyron L/S Shirt in Blue $69.00$99.00

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Original Penguin Tyron L/S Shirt in Blue

Original Penguin Tyron L/S Shirt in Blue

$69.00$99.00

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An oxford shirt is a necessity in every man's wardrobe, and this one from Original Penguin has caught our attention with its multicoloured gingham print. It's cut for a slim fit but crafted with soft stretch cotton to keep you comfortable and moving. Featuring a mini collar, the button-down shirt has chest pocket which is finished with a subtle Penguin logo embroidery.

This Style from Penguin is also available in Other Colors.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Tyron L/S Shirt in Red Original Penguin Tyron L/S Shirt in Red Original Penguin Tyron L/S Shirt in Red $59.00$99.00

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Original Penguin Tyron L/S Shirt in Red

Original Penguin Tyron L/S Shirt in Red

$59.00$99.00

View all product details

An oxford shirt is a necessity in every man's wardrobe, and this one from Original Penguin has caught our attention with its multicoloured gingham print. It's cut for a slim fit but crafted with soft stretch cotton to keep you comfortable and moving. Featuring a mini collar, the button-down shirt has chest pocket which is finished with a subtle Penguin logo embroidery.

This Style from Penguin is also available in Other Colors.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Augustus L/S Shirt in Plum Original Penguin Augustus L/S Shirt in Plum Original Penguin Augustus L/S Shirt in Plum $69.00$99.00

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Original Penguin Augustus L/S Shirt in Plum

Original Penguin Augustus L/S Shirt in Plum

$69.00$99.00

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Inject a dose of deep plum into your wardrobe with this mini gingham long sleeve shirt. Featuring a mini collar and button placket, its cotton dobby fabrication adds dimension to your look. Cut for a slim fit, the chest pocket is finished with a subtle Penguin logo embroidery.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton Machine Washable


Quick View Original Penguin Olen Zip Up in Navy Original Penguin Olen Zip Up in Navy Original Penguin Olen Zip Up in Navy $64.00$128.00

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Original Penguin Olen Zip Up in Navy

Original Penguin Olen Zip Up in Navy

$64.00$128.00

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A stylish sports jacket will prove indispensable to your style arsenal and this quilted version from Original Penguin is especially handsome. Crafted from a double knit jacquard fabrication for warmth and comfort, this sleek bomber-style piece features a front zip closure, secure pockets, and a crew neck collar.

Also available in store at Roadtrip.

Heritage Slim Fit

59% Cotton, 41% Polyester

Machine Washable


Quick View Original Penguin Damion Henley in Navy Original Penguin Damion Henley in Navy Original Penguin Damion Henley in Navy $62.00$89.00

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Original Penguin Damion Henley in Navy

Original Penguin Damion Henley in Navy

$62.00$89.00

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A waffled texture is one more reason to love your go-to henley even more. Classic in its three-button closure, the slim fit design features a thermal fabrication and is finished with a subtle Penguin logo embroidery at the chest.

Also available in store at Roadtrip.

Heritage Slim Fit

78% Cotton, 22% Polyester

Machine Washable


Quick View Original Penguin Ottawa Milford Henley in Black Original Penguin Ottawa Milford Henley in Black Original Penguin Ottawa Milford Henley in Black $52.00$75.00

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Original Penguin Ottawa Milford Henley in Black

Original Penguin Ottawa Milford Henley in Black

$52.00$75.00

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Speckled to perfection, this henley is an essential to every man's casual closet. It's crafted from super soft cotton with all the features of the classic design: a henley collar and three-button closure. The slim fit style is finished with the famous Penguin logo embroidery at the chest.

This Style from Penguin is also available in Other Colors.

Also available in store at Roadtrip.

Heritage Slim Fit

58% Cotton, 42% Polyester

Machine Washable


Quick View Original Penguin Lenard Polo in Black Original Penguin Lenard Polo in Black Original Penguin Lenard Polo in Black $34.00$69.00

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Original Penguin Lenard Polo in Black

Original Penguin Lenard Polo in Black

$34.00$69.00

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This black polo gets a modern update with an allover speckled print on an otherwise classic design; it features a self collar and three-button placket. Crafted from a soft cotton jersey fabrication, it comes in the brand's Heritage Slim Fit for a look that's sleek and comfortable.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin On The Rocks Sweater in Hunter Original Penguin On The Rocks Sweater in Hunter Original Penguin On The Rocks Sweater in Hunter $62.00$89.00

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Original Penguin On The Rocks Sweater in Hunter

Original Penguin On The Rocks Sweater in Hunter

$62.00$89.00

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This Classic Fit V-neck sweater is crafted from 100% Lambswool; super soft and sure to keep you warm and comfortable. It's finished with ribbed trims and the famous Penguin logo embroidery at the chest for timeless appeal.

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

Also available in store at Roadtrip.

Classic Fit

100% Lambswool

Dry Clean Only


Quick View Original Penguin On The Rocks Sweater in Navy Original Penguin On The Rocks Sweater in Navy Original Penguin On The Rocks Sweater in Navy $62.00$89.00

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Original Penguin On The Rocks Sweater in Navy

Original Penguin On The Rocks Sweater in Navy

$62.00$89.00

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This Classic Fit V-neck sweater is crafted from 100% Lambswool; super soft and sure to keep you warm and comfortable. It's finished with ribbed trims and the famous Penguin logo embroidery at the chest for timeless appeal.

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

Also available in store at Roadtrip.

Classic Fit

100% Lambswool

Dry Clean Only


Page: 123

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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.


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