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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 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 Classic Logo Tee in Navy Original Penguin Classic Logo Tee in Navy Original Penguin Classic Logo Tee in Navy $55.00

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Original Penguin Classic Logo Tee in Navy

Original Penguin Classic Logo Tee in Navy

$55.00

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This tee is as classic as it gets! In a versatile navy hue that can be worn all year long, this slim fit crew features the iconic Penguin logo at the front with a raised soft texture for an added twist. Crafted from 100% cotton, it's the perfect T-Shirt to throw on and go to look put together.

Also available in store at Roadtrip.

Slim Fit

100% Cotton

Machine Washable


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

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Original Penguin Owens L/S Shirt in Grey

Original Penguin Owens L/S Shirt in Grey

$99.00

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The ultimate comfortable button-up shirt, this navy-grey staple is sure to be a favourite. Crafted from a stretch cotton, this heathered long sleeve is not restrictive in any way thanks to its knitted oxford fabrication, and features a chest pocket with the iconic Penguin logo. Throw it on with shorts and trousers alike.

Also available in store at Roadtrip.

Slim Fit

65% Cotton, 35% Polyester

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 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 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 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 Bridgeport Polo in Blue Original Penguin Bridgeport Polo in Blue $79.00

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Original Penguin Bridgeport Polo in Blue

Original Penguin Bridgeport Polo in Blue

$79.00

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What's better than two-in-one? Absolutely nothing! Penguin has delivered once again knowing that all guys have a penchant for something reversible! This handsome blue polo is simple yet smart in its fabrication; it's cut for a slim fit and features the penguin logo at the chest on either side. Whether you wear it the cotton-pique way, or the smoother side, this will be a sure favourite and will pair perfectly with all denim!

Also available in store at Roadtrip.

Heritage Slim Fit

68% Cotton, 32% Polyester

Machine Washable


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

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Original Penguin Whitby L/S Shirt in Navy

Original Penguin Whitby L/S Shirt in Navy

$99.00

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Original Penguin is known for its expert craftsmanship and proves this time and time again. Made from linen for superior breathability, this navy flecked shirt has a textured finish and an embroidered logo on the chest pocket. Wear yours to the office with black trousers and brogues, or unbutton it and pair with shorts and a white tee for barbecues and beers.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Linen

Machine Wash Cold


Quick View Original Penguin Calgary Shorts in Black Original Penguin Calgary Shorts in Black Original Penguin Calgary Shorts in Black $79.00

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Original Penguin Calgary Shorts in Black

Original Penguin Calgary Shorts in Black

$79.00

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Original Penguin's contemporary staples will form a firm foundation to your warm-weather wardrobe, and these straight fit shorts are a good place to start. They're cut from lightweight stretch-cotton, making them a smart choice for the guy on the move, especially when the mercury climbs. Easy and breezy, wear this timeless style with everything from printed shirts to clean-cut tees.

These Shorts from Penguin are also available in Other Colors.

Also available in store at Roadtrip or Trustfund.

Straight fit

98% Cotton, 2% Spandex

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


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 Quintin L/S Tee in Navy Original Penguin Quintin L/S Tee in Navy Original Penguin Quintin L/S Tee in Navy $55.00$79.00

Added to Your Tote!

Original Penguin Quintin L/S Tee in Navy

Original Penguin Quintin L/S Tee in Navy

$55.00$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 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 Say My Name L/S Shirt in Navy Original Penguin Say My Name L/S Shirt in Navy $69.00$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

$69.00$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 $64.00$99.00

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Original Penguin Colorado L/S Shirt in Green

Original Penguin Colorado L/S Shirt in Green

$64.00$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 Visalia L/S Shirt in Blue Original Penguin Visalia L/S Shirt in Blue $59.00$99.00

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Original Penguin Visalia L/S Shirt in Blue

Original Penguin Visalia L/S Shirt in Blue

$59.00$99.00

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Wow 'em when you walk by in this eye-catching shirt from Original Penguin. With your ultimate comfort in mind, it's crafted from soft cotton and perfectly tailored for the best possible fit. Complete with the famous penguin embroidery at the chest pocket, this long sleeve button up features a cool heathered design that will bring you from the office to drinks at your go-to sports bar.

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 Burlington Polo in White Original Penguin Burlington Polo in White Original Penguin Burlington Polo in White $49.00$79.00

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Original Penguin Burlington Polo in White

Original Penguin Burlington Polo in White

$49.00$79.00

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Experts in classic pieces, Original Penguin knows a thing or two about the polo game! Crafted with a smart slim fit, this stretch-cotton polo shirt is comfortable enough for a day out on the water and smart enough for a tipple at the club. You'll love the 4-button elongated placket and buttoned chest pocket! Embrace the look wholeheartedly with a pair of white chinos, or go for a more subtle option with jeans.

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

Also available in store at Trustfund.

Heritage Slim Fit

100% Pima Cotton

Machine Wash Cold


Quick View Original Penguin Sherbrooke L/S Shirt in Teal Original Penguin Sherbrooke L/S Shirt in Teal $69.00$99.00

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Original Penguin Sherbrooke L/S Shirt in Teal

Original Penguin Sherbrooke L/S Shirt in Teal

$69.00$99.00

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Turn heads in this mini gingham print top from Original Penguin. The eye-catching teal hue and dobby texture make for an irresistible piece! Tailor made for gentlemen in a slim fit from 100% cotton, wear tucked in with a tie or dressed down with rolled up sleeves and jeans.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Saskatoon L/S Shirt in Blues Original Penguin Saskatoon L/S Shirt in Blues Original Penguin Saskatoon L/S Shirt in Blues $49.00$99.00

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Original Penguin Saskatoon L/S Shirt in Blues

Original Penguin Saskatoon L/S Shirt in Blues

$49.00$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 blue 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 Barrie L/S Shirt in Green Original Penguin Barrie L/S Shirt in Green Original Penguin Barrie L/S Shirt in Green $69.00$99.00

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Original Penguin Barrie L/S Shirt in Green

Original Penguin Barrie L/S Shirt in Green

$69.00$99.00

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With its pearl-finish front button placket, this Original Penguin shirt brings a smart air with a fresh take. This is thanks to the pastel-hued cotton cloth and neat, slim fit through the body. Finished with a curved hem and the iconic penguin logo embroidered at the chest, try the button-down collar piece with a knitted tie under a blazer for a well-balanced outfit. Roll up the cuffs to display the contrasting checked lining!

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Calgary Shorts in Navy Original Penguin Calgary Shorts in Navy Original Penguin Calgary Shorts in Navy $45.00$79.00

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Original Penguin Calgary Shorts in Navy

Original Penguin Calgary Shorts in Navy

$45.00$79.00

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Original Penguin's contemporary staples will form a firm foundation to your warm-weather wardrobe, and these straight fit shorts are a good place to start. They're cut from lightweight stretch-cotton, making them a smart choice for the guy on the move, especially when the mercury climbs. Easy and breezy, wear this timeless style with everything from printed shirts to clean-cut tees.

These Shorts from Penguin are also available in Other Colors.

Also available in store at Roadtrip.

Straight fit

98% Cotton, 2% Spandex

Machine Washable


Quick View Original Penguin Calgary Shorts in Grey Original Penguin Calgary Shorts in Grey Original Penguin Calgary Shorts in Grey $45.00$79.00

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Original Penguin Calgary Shorts in Grey

Original Penguin Calgary Shorts in Grey

$45.00$79.00

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Original Penguin's contemporary staples will form a firm foundation to your warm-weather wardrobe, and these straight fit shorts are a good place to start. They're cut from lightweight stretch-cotton, making them a smart choice for the guy on the move, especially when the mercury climbs. Easy and breezy, wear this timeless style with everything from printed shirts to clean-cut tees.

These Shorts from Penguin are also available in Other Colors.

Also available in store at Roadtrip.

Straight fit

98% Cotton, 2% Spandex

Machine Washable


Quick View Original Penguin Calgary Shorts in Khaki Original Penguin Calgary Shorts in Khaki Original Penguin Calgary Shorts in Khaki $45.00$79.00

Added to Your Tote!

Original Penguin Calgary Shorts in Khaki

Original Penguin Calgary Shorts in Khaki

$45.00$79.00

View all product details

Original Penguin's contemporary staples will form a firm foundation to your warm-weather wardrobe, and these straight fit shorts are a good place to start. They're cut from lightweight stretch-cotton, making them a smart choice for the guy on the move, especially when the mercury climbs. Easy and breezy, wear this timeless style with everything from printed shirts to clean-cut tees.

These Shorts from Penguin are also available in Other Colors.

Also available in store at Roadtrip.

Straight fit

98% Cotton, 2% Spandex

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.


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