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

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Original Penguin Bertram L/S Shirt in Grape

Original Penguin Bertram L/S Shirt in Grape

$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 $99.00

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Original Penguin Delmer L/S Shirt Navy

Original Penguin Delmer L/S Shirt Navy

$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 $99.00

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Original Penguin Milo L/S Shirt in Grape

Original Penguin Milo L/S Shirt in Grape

$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 $99.00

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Original Penguin Brenton Flannel L/S in Plum

Original Penguin Brenton Flannel L/S in Plum

$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 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 Donn L/S Shirt in Sky Original Penguin Donn L/S Shirt in Sky Original Penguin Donn L/S Shirt in Sky $99.00

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Original Penguin Donn L/S Shirt in Sky

Original Penguin Donn L/S Shirt in Sky

$99.00

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This shirt is the perfect combination of pattern. Its white cotton fabrication features a mini blue check, as well as subtle yellow and blue dots for a look that's fresh and still timeless. Cut for a slim fit, the button-down style features a curved hem and chest pocket with the iconic 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 $99.00

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Original Penguin Tyron L/S Shirt in Blue

Original Penguin Tyron L/S Shirt in Blue

$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 $99.00

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Original Penguin Tyron L/S Shirt in Red

Original Penguin Tyron L/S Shirt in Red

$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 Augustus L/S Shirt in Plum Original Penguin Augustus L/S Shirt in Plum Original Penguin Augustus L/S Shirt in Plum $99.00

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Original Penguin Augustus L/S Shirt in Plum

Original Penguin Augustus L/S Shirt in Plum

$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 Halifax Tee in Ice Original Penguin Halifax Tee in Ice Original Penguin Halifax Tee in Ice $49.00

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Original Penguin Halifax Tee in Ice

Original Penguin Halifax Tee in Ice

$49.00

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Made for laid-back weekends at home, this Original Penguin tee features a soft vintage fabrication, promising nothing but ultra comfort. An Original Penguin logo is the tee's only needed print. Perfect to pair with your favourite denim and a lightweight jacket, this tee will be your most trusted companion on Saturdays.

Also available in store at Roadtrip.

Heritage Slim Fit

50% Polyester, 37% Cotton, 13% Rayon

Machine Washable


Quick View Original Penguin Judson Tee in Grey Original Penguin Judson Tee in Grey Original Penguin Judson Tee in Grey $49.00

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Original Penguin Judson Tee in Grey

Original Penguin Judson Tee in Grey

$49.00

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Original Penguin's classic logo tee gets a fun twist with a paint splash design in the penguin graphic. The slim fit and soft cotton blend jersey make it look as good as it feels.

Also available in store at Roadtrip.

Heritage Slim Fit

60% Cotton, 40% Polyester

Machine Washable


Quick View Original Penguin Wilton Polo in Grey Original Penguin Wilton Polo in Grey Original Penguin Wilton Polo in Grey $75.00

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Original Penguin Wilton Polo in Grey

Original Penguin Wilton Polo in Grey

$75.00

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Simple yet unique, this polo is a signature classic of Original Penguin with its self collar, three-button placket and cotton-pique fabrication. Cut for a slim fit, it features distinctive red outlines on the placket, sleeves, and collar. A must-have for the modern man, it's finished with a chest pocket embroidered with the iconic Penguin logo.

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 Olen Zip Up in Navy Original Penguin Olen Zip Up in Navy Original Penguin Olen Zip Up in Navy $128.00

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Original Penguin Olen Zip Up in Navy

Original Penguin Olen Zip Up in Navy

$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 $89.00

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Original Penguin Damion Henley in Navy

Original Penguin Damion Henley in Navy

$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 Cream Original Penguin Ottawa Milford Henley in Cream Original Penguin Ottawa Milford Henley in Cream $75.00

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Original Penguin Ottawa Milford Henley in Cream

Original Penguin Ottawa Milford Henley in Cream

$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 a subtle 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 Ottawa Milford Henley in Black Original Penguin Ottawa Milford Henley in Black Original Penguin Ottawa Milford Henley in Black $75.00

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Original Penguin Ottawa Milford Henley in Black

Original Penguin Ottawa Milford Henley in Black

$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 $69.00

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Original Penguin Lenard Polo in Black

Original Penguin Lenard Polo in Black

$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 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 On The Rocks Sweater in Hunter Original Penguin On The Rocks Sweater in Hunter Original Penguin On The Rocks Sweater in Hunter $89.00

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Original Penguin On The Rocks Sweater in Hunter

Original Penguin On The Rocks Sweater in Hunter

$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 $89.00

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Original Penguin On The Rocks Sweater in Navy

Original Penguin On The Rocks Sweater in Navy

$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 Happy Times Sweater in Plum Original Penguin Happy Times Sweater in Plum Original Penguin Happy Times Sweater in Plum $89.00

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Original Penguin Happy Times Sweater in Plum

Original Penguin Happy Times Sweater in Plum

$89.00

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A cotton pique fabrication gives great texture to this comfortable crew neck sweater in a handsome deep plum hue. Finished with ribbed trims and the iconic Penguin logo embroidered at the chest, this will look great layered over a plaid button-up!

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


Quick View Original Penguin Say My Name L/S Shirt in Navy Original Penguin Say My Name L/S Shirt in Navy $99.00

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Original Penguin Say My Name L/S Shirt in Navy

Original Penguin Say My Name L/S Shirt in Navy

$99.00

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Original Penguin's cotton shirt is a fine example of the label's take on dapper dressing. In a suave navy and white gingham print, this slim-fit shirt is cool and contemporary and will look particularly smart against darker tones. Featuring a curved hemline, this must-have is crafted with a comfortable stretch interlining for the guy on the move. Let your cuffs peek out from under a dark blazer at the office.

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

Also available in store at Roadtrip.

Heritage Slim Fit

98% Cotton, 2% Elastane

Machine Wash Cold


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

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Original Penguin Colorado L/S Shirt in Green

Original Penguin Colorado L/S Shirt in Green

$99.00

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For a plaid that pops, you can rely on Original Penguin to have your back! Cut for a smart slim fit, this cotton button-up shirt combines handsome hues for a standout look. Crafted for extensible stretch, it's comfortable and features the classic embroidered logo on the chest pocket. Rev up your weekend wear by sporting it unbuttoned with a white tee and jeans.

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

Also available in store at Trustfund.

Heritage Slim Fit

100% Cotton

Machine Wash Cold


Quick View Original Penguin Grand Rapids Tee in Blue Original Penguin Grand Rapids Tee in Blue $59.00

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Original Penguin Grand Rapids Tee in Blue

Original Penguin Grand Rapids Tee in Blue

$59.00

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Comfort is always key with Original Penguin and this tee is no exception to the rule! Perfect for casual days, this striped shirt features a classic henley design with its three-button placket. The soft cotton fabrication keeps you comfortable, while the slim fit keeps you looking sharp. Finished with the penguin logo embroidery at the chest, wear it with jeans on lazy Sundays or out to a picnic!

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

Also available in store at Roadtrip.

Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Grand Rapids Tee in Grey Original Penguin Grand Rapids Tee in Grey $59.00

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Original Penguin Grand Rapids Tee in Grey

Original Penguin Grand Rapids Tee in Grey

$59.00

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Comfort is always key with Original Penguin and this tee is no exception to the rule! Perfect for casual days, this striped shirt features a classic henley design with its three-button placket. The soft cotton fabrication keeps you comfy, while the slim fit keeps you looking sharp. Finished with the penguin logo embroidery at the chest, wear it with jeans on lazy Sundays or out to a picnic!

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

Also available in store at Roadtrip.

Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Saskatoon L/S Shirt in Peach Original Penguin Saskatoon L/S Shirt in Peach Original Penguin Saskatoon L/S Shirt in Peach $69.00$99.00

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Original Penguin Saskatoon L/S Shirt in Peach

Original Penguin Saskatoon L/S Shirt in Peach

$69.00$99.00

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Button-up and look instantly dapper in this plaid shirt from Original Penguin. Complete with a mini collar and monogrammed pocket, this heritage slim fit long-sleeve with rounded hem will instantly become a fan favourite in your wardrobe! Handsome olive and peach hues create a great colour combo and a cotton fabrication keeps things light and comfortable. Brighten your look by adding this shirt to navy work suiting or dark denim.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Wash Cold


Quick View Original Penguin High Road S/S Shirt in Navy Original Penguin High Road S/S Shirt in Navy $69.00$89.00

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Original Penguin High Road S/S Shirt in Navy

Original Penguin High Road S/S Shirt in Navy

$69.00$89.00

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Original Penguin delivers classics made from luxurious, well-treated fabrics. This shirt is cut from lightweight linen to keep you breezy and features an awesome blue and sand plaid to keep you looking cool. Who doesn't love the chest pocket with embroidered logo? Designed for a classic slim cut, it'll see you through the warmer months with ease – simply throw on with a pair of shorts or chinos for alfresco lunches or a trip to your local brewery.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Linen

Machine Washable


Quick View Original Penguin Lake Ontario Shorts in Blue Original Penguin Lake Ontario Shorts in Blue Original Penguin Lake Ontario Shorts in Blue $55.00$89.00

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Original Penguin Lake Ontario Shorts in Blue

Original Penguin Lake Ontario Shorts in Blue

$55.00$89.00

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With a focus on precise cuts for a superior fit, Original Penguin specialises in smart and stylish trousers. These slim fit shorts are made from lightweight cotton chambray that's perfectly suited to warm weather. You'll love the twill fabric lining on the interior waistband and gingham patterned tape for added detail. Try yours with an Oxford shirt in a complementary shade of blue.

Also available in store at Trustfund.

Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Sunnyvale S/S Shirt in Denim Original Penguin Sunnyvale S/S Shirt in Denim $59.00$89.00

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Original Penguin Sunnyvale S/S Shirt in Denim

Original Penguin Sunnyvale S/S Shirt in Denim

$59.00$89.00

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Original Penguin is known for its classic designs, yet always brings something new and exciting to the table, and this short sleeve button-up is just that! In a cool denim hue for the modern man, it's sparsely splayed with a mini argyle-like print throughout for just the right hint of pattern. Slim in fit, this cotton piece is also crafted from elastane to ensure you stay cool and comfortable. Simply pair with lightweight navy shorts or trousers and you'll be cruisin'!

Also available in store at Roadtrip.

Heritage Slim Fit

98% Cotton, 2% Elastane

Machine Washable


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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