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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 Hold On L/S Shirt in Navy Original Penguin Hold On L/S Shirt in Navy Original Penguin Hold On L/S Shirt in Navy $98.00

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Original Penguin Hold On L/S Shirt in Navy

Original Penguin Hold On L/S Shirt in Navy

$98.00

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Rustic and refined is the name of the game with this casual plaid long sleeve from Original Penguin. Outfitted with an embroidered pocket logo and a classic slim fit, this shirt is an easy pick for an effortless look. Head to the lecture hall or to a company breakfast in style wearing this cool toned plaid with black jeans and a blazer over top.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Roadhouse Henley in Grey Original Penguin Roadhouse Henley in Grey Original Penguin Roadhouse Henley in Grey $78.00

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Original Penguin Roadhouse Henley in Grey

Original Penguin Roadhouse Henley in Grey

$78.00

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Original Penguin's striped long sleeve tee will make a fine addition to your casual staples. Crafted from supremely soft cotton, it features a classic henley collar and a yarn dyed fabric finish. Complete with the iconic Penguin logo embroidered at the chest, wear yours with jeans or chinos on casual days.

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

Also available in store at Roadtrip.

100% Cotton

Machine Washable


Quick View Original Penguin Own Way L/S Shirt in Navy Original Penguin Own Way L/S Shirt in Navy $98.00

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Original Penguin Own Way L/S Shirt in Navy

Original Penguin Own Way L/S Shirt in Navy

$98.00

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Get ready to button and go in this checked print long sleeve shirt from Original Penguin. Its easy-to-style hologram pattern and mini collar make this suave button-down a must-have for any sartorially savvy gentleman. Pair it with khakis and black jeans for a slick evening look.

Also available in store at Roadtrip.

Heritage Slim Fit

Mini Collar

100% Cotton

Machine Washable


Quick View Original Penguin Famous Tee in Coal Original Penguin Famous Tee in Coal $45.00

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Original Penguin Famous Tee in Coal

Original Penguin Famous Tee in Coal

$45.00

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No talent? No problem! Live the American dream of being famous for absolutely nothing and sport this cheeky tee from Penguin. Crafted from a soft cotton blend, this heathered grey crew neck is cut for a comfortable slim fit. A guaranteed conversation-starter, wear it to your next party or on weekend down-time with jeans.

Also available in store at Roadtrip.

Heritage Slim Fit

60% Cotton, 40% Polyester

Machine Washable


Quick View Original Penguin Swift Reversible Long Sleeve in Grey Original Penguin Swift Reversible Long Sleeve in Grey Original Penguin Swift Reversible Long Sleeve in Grey $78.00

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Original Penguin Swift Reversible Long Sleeve in Grey

Original Penguin Swift Reversible Long Sleeve in Grey

$78.00

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For mornings that last all afternoon, Original Penguin has got you covered with this reversible long sleeve. Offering two styles in one, choose to wear this super soft shirt on the solid side, or kick things up a notch and wear it on the striped side. Cut in a classic slim fit tee design, the touchable cotton crew is finished with a contrasting Penguin logo embroidered at the chest. Throw on with slim joggers for lazy Sundays, switching out for jeans when you venture out of the house.

This style from Penguin is also available in Other Colors.

Also available in store at Roadtrip.

Heritage Slim Fit

60% Cotton, 40% Polyester

Machine Washable


Quick View Original Penguin Swift Reversible Long Sleeve in Coal Original Penguin Swift Reversible Long Sleeve in Coal Original Penguin Swift Reversible Long Sleeve in Coal $78.00

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Original Penguin Swift Reversible Long Sleeve in Coal

Original Penguin Swift Reversible Long Sleeve in Coal

$78.00

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For mornings that last all afternoon, Original Penguin has got you covered with this reversible long sleeve. Offering two styles in one, choose to wear this super soft shirt on the solid side, or kick things up a notch and wear it on the striped side. Cut in a classic slim fit tee design, the touchable cotton crew is finished with a contrasting Penguin logo embroidered at the chest. Throw on with slim joggers for lazy Sundays, switching out for jeans when you venture out of the house.

This style from Penguin is also available in Other Colors.

Also available in store at Roadtrip.

Heritage Slim Fit

60% Cotton, 40% Polyester

Machine Washable


Quick View Original Penguin Northern Way L/S Shirt in Blues Original Penguin Northern Way L/S Shirt in Blues Original Penguin Northern Way L/S Shirt in Blues $98.00

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Original Penguin Northern Way L/S Shirt in Blues

Original Penguin Northern Way L/S Shirt in Blues

$98.00

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No man's casual wardrobe is complete without a dependable checked shirt, and this tonal-blue, green and white style from Original Penguin ticks all the right boxes. This classic plaid design features a button-down collar and slim cut for a comfortable fit. Featuring a rounded hem, the pure cotton composition makes this piece both lightweight and breathable. Wear it year-round with your favourite denim, switching to shorts when the weather warms.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Curtis Henley in River Original Penguin Curtis Henley in River $75.00$108.00

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Original Penguin Curtis Henley in River

Original Penguin Curtis Henley in River

$75.00$108.00

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Original Penguin has designed this henley with minimal detailing - it's entirely blue and has a simple 3-button placket. This places all the emphasis on the fabric, which is woven from pure cotton with a herringbone pattern and a soft finish. We love the embroidered Penguin logo at the chest and contrasting neck for finishing touches! It's a smart way to add interest to pared-back outfits.

Also available in store at Roadtrip.

100% Cotton

Machine Washable


Quick View Original Penguin Dapper Hour V-Neck Sweater in Sky Original Penguin Dapper Hour V-Neck Sweater in Sky Original Penguin Dapper Hour V-Neck Sweater in Sky $59.00$98.00

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Original Penguin Dapper Hour V-Neck Sweater in Sky

Original Penguin Dapper Hour V-Neck Sweater in Sky

$59.00$98.00

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There's nothing like a perfect wool v-neck sweater to complete your autumn/winter wardrobe. Don't underestimate the simplicity of this v-neck; its tailored slim fit and rib-knit detailing make it a modern classic. Wear it over a patterned button-down and a sports jacket or with chinos for a sophisticated casual look.

This Sweater from Original Penguin is also available in Other Colors

Also available in store at Roadtrip.

100% Wool

Machine Washable


Quick View Original Penguin Dapper Hour V-Neck Sweater in Grey Original Penguin Dapper Hour V-Neck Sweater in Grey Original Penguin Dapper Hour V-Neck Sweater in Grey $59.00$98.00

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Original Penguin Dapper Hour V-Neck Sweater in Grey

Original Penguin Dapper Hour V-Neck Sweater in Grey

$59.00$98.00

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There's nothing like a perfect wool v-neck sweater to complete your autumn/winter wardrobe. Don't underestimate the simplicity of this v-neck; its tailored slim fit and rib-knit detailing make it a modern classic. Wear it over a patterned button-down and a sports jacket or with chinos for a sophisticated casual look.

This Sweater from Original Penguin is also available in Other Colors

Also available in store at Trustfund.

100% Wool

Machine Washable


Quick View Original Penguin Dapper Hour V-Neck Sweater in Brown Original Penguin Dapper Hour V-Neck Sweater in Brown Original Penguin Dapper Hour V-Neck Sweater in Brown $59.00$98.00

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Original Penguin Dapper Hour V-Neck Sweater in Brown

Original Penguin Dapper Hour V-Neck Sweater in Brown

$59.00$98.00

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There's nothing like a perfect wool v-neck sweater to complete your autumn/winter wardrobe. Don't underestimate the simplicity of this v-neck; its tailored slim fit and rib-knit detailing make it a modern classic. Wear it over a patterned button-down and a sports jacket or with chinos for a sophisticated casual look.

This Sweater from Original Penguin is also available in Other Colors

Also available in store at Roadtrip and Trustfund.

100% Wool

Machine Washable


Quick View Original Penguin Rough Days Crew Sweater in Navy Original Penguin Rough Days Crew Sweater in Navy Original Penguin Rough Days Crew Sweater in Navy $59.00$98.00

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Original Penguin Rough Days Crew Sweater in Navy

Original Penguin Rough Days Crew Sweater in Navy

$59.00$98.00

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Cozy up with this knit sweater from Original Penguin. This crew neck sweater is a medium weight, boasting perfectly ribbed knit detailing at the cuff/hem and a soft lamb's wool fabrication. Wear it at the office over a oxford button-down or with black jeans for an understated evening look!

This Sweater from Original Penguin is also available in Other Colors

Also available in store at Roadtrip.

100% Lambs Wool

Dry Clean Only


Quick View Original Penguin Rough Days Crew Sweater in Black Original Penguin Rough Days Crew Sweater in Black Original Penguin Rough Days Crew Sweater in Black $59.00$98.00

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Original Penguin Rough Days Crew Sweater in Black

Original Penguin Rough Days Crew Sweater in Black

$59.00$98.00

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Cozy up with this knit sweater from Original Penguin. This crew neck sweater is a medium weight, boasting perfectly ribbed knit detailing at the cuff/hem and a soft lamb's wool fabrication. Wear it at the office over a oxford button-down or with black jeans for an understated evening look!

This Sweater from Original Penguin is also available in Other Colors

Also available in store at Roadtrip.

100% Lambs Wool

Dry Clean Only


Quick View Original Penguin One Good Fella Shirt in Navy Original Penguin One Good Fella Shirt in Navy $49.00$98.00

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Original Penguin One Good Fella Shirt in Navy

Original Penguin One Good Fella Shirt in Navy

$49.00$98.00

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Mad about plaid? We recommend getting your hands on this perfectly pattered shirt from Original Penguin. This classic plaid button-down boasts a monogrammed pocket and a fan favourite heritage fit. In addition to that, its understated plaid print makes this the perfect shirt to pair with khaki shorts or under a brown blazer!

Also available in store at Roadtrip.

100% Cotton

Machine Washable


Quick View Original Penguin Perfect Strangers L/S Shirt in Blue Original Penguin Perfect Strangers L/S Shirt in Blue $69.00$98.00

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Original Penguin Perfect Strangers L/S Shirt in Blue

Original Penguin Perfect Strangers L/S Shirt in Blue

$69.00$98.00

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'Laid-back cool' just got an update with this sleek gingham shirt from Original Penguin. Its subtle print, plainweave fabrication, and spread collar are guaranteed to have you reaching for this button-down, no matter the occasion. Mix and match in this shirt with chinos and a skinny tie or jeans and a slim-fit cardigan for an easy, yet stylish look.

Also available in store at Roadtrip and Trustfund.

100% Cotton

Machine Washable

Slim Fit


Quick View Original Penguin Duncan L/S Shirt in Grey Original Penguin Duncan L/S Shirt in Grey Original Penguin Duncan L/S Shirt in Grey $49.00$98.00

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Original Penguin Duncan L/S Shirt in Grey

Original Penguin Duncan L/S Shirt in Grey

$49.00$98.00

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A shirt that's as handsome and charming as you! Decorated with a subtly textured polka dot and cut for a slim fit, Penguin has created yet another classic piece. This easy-going button-down is fabricated in a lightweight, steel-hued chambray to keep you looking cool 'n collected no matter the event. It'll take you from date night to hockey night without a hitch! Our fave outfit is rolled up sleeves and tucked into a comfy pair of khakis with a sleek pair of sneakers.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Cooper Polo in Navy Original Penguin Cooper Polo in Navy Original Penguin Cooper Polo in Navy $62.00$88.00

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Original Penguin Cooper Polo in Navy

Original Penguin Cooper Polo in Navy

$62.00$88.00

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From the gentleman playing golf at the club to the dude hitting the clubs, this polo in complementary stripes will keep you looking sharp! In an easy-to-wear and breathable cotton, Penguin's classic polo style is accentuated by a contrasting collar and finished with the iconic Penguin logo embroidered at the chest. Get a perfect score by matching this handsome slim fit shirt with a timeless pair of khakis!

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin High Point Shorts in Grey Original Penguin High Point Shorts in Grey Original Penguin High Point Shorts in Grey $59.00$98.00

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Original Penguin High Point Shorts in Grey

Original Penguin High Point Shorts in Grey

$59.00$98.00

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Nothing says weekend wear like a pair of crisp white and grey shorts, and this Original Penguin style is an ideal base for soft linen shirts or vibrant printed tees. Cut for a slim yet comfortable fit, this must-have piece features a timeless plaid check. In lightweight, breathable cotton, they'll make an astute addition to your warm-weather arsenal.

Also available in store at Roadtrip.

Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Atticus Shorts in Cobalt Original Penguin Atticus Shorts in Cobalt $49.00$78.00

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Original Penguin Atticus Shorts in Cobalt

Original Penguin Atticus Shorts in Cobalt

$49.00$78.00

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Original Penguin's shorts are sure to become a key player in your warm-weather wardrobe. Woven from robust cotton in a timeless shade, they're a no-brainer option for summer. Try dressing up the 5-pocket style with a linen shirt and unstructured blazer, or take them to the beach with sunglasses and sandals.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Milo L/S Shirt in Ocean Original Penguin Milo L/S Shirt in Ocean $69.00$98.00

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Original Penguin Milo L/S Shirt in Ocean

Original Penguin Milo L/S Shirt in Ocean

$69.00$98.00

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Original Penguin looks to its archive to create authentic pieces and this gingham shirt is a handsome example. Crafted from lightweight cotton, this long sleeve is finished with workwear-inspired detailing including the curved hem and mini collar. In a cool blue and black check, this piece is finished with the famous logo embroidery at the chest.

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

Also available in store at Roadtrip.

Heritage Classic Fit

100% Cotton

Machine Washable


Quick View Original Penguin Atticus Shorts in Blue Original Penguin Atticus Shorts in Blue Original Penguin Atticus Shorts in Blue $49.00$78.00

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Original Penguin Atticus Shorts in Blue

Original Penguin Atticus Shorts in Blue

$49.00$78.00

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Original Penguin's shorts are sure to become a key player in your warm-weather wardrobe. Woven from robust cotton in a timeless shade, they're a no-brainer option for summer. Try dressing up the 5-pocket style with a linen shirt and unstructured blazer, or take them to the beach with sunglasses and sandals.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Atticus Shorts in Navy Original Penguin Atticus Shorts in Navy $49.00$78.00

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Original Penguin Atticus Shorts in Navy

Original Penguin Atticus Shorts in Navy

$49.00$78.00

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Original Penguin's shorts are sure to become a key player in your warm-weather wardrobe. Woven from robust cotton in a timeless shade, they're a no-brainer option for summer. Try dressing up the 5-pocket style with a linen shirt and unstructured blazer, or take them to the beach with sunglasses and sandals.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Atticus Shorts in Khaki Original Penguin Atticus Shorts in Khaki $49.00$78.00

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Original Penguin Atticus Shorts in Khaki

Original Penguin Atticus Shorts in Khaki

$49.00$78.00

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Original Penguin's shorts are sure to become a key player in your warm-weather wardrobe. Woven from robust cotton in a timeless shade, they're a no-brainer option for summer. Try dressing up the 5-pocket style with a linen shirt and unstructured blazer, or take them to the beach with sunglasses and sandals.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

Slim Fit

100% Cotton

Machine Washable


Quick View Original Penguin Wise Guy Sweater in Black Original Penguin Wise Guy Sweater in Black $65.00$108.00

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Original Penguin Wise Guy Sweater in Black

Original Penguin Wise Guy Sweater in Black

$65.00$108.00

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This stunning wide striped sweater from Original Penguin is the perfect versatile piece for your wardrobe. Featuring a long-sleeve construction and soft fabrication, the sweater promises a clean-cut look that will keep you warm. Its bold stripe offers an eye-catching look that stays understated and charming. Pair with black denim and and a leather jacket for a cool, casual look.

Also available in store at Roadtrip.

100% Lambswool

Dry Clean Only


Quick View Original Penguin Galway Guy L/S Shirt in Denim Original Penguin Galway Guy L/S Shirt in Denim Original Penguin Galway Guy L/S Shirt in Denim $49.00$98.00

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Original Penguin Galway Guy L/S Shirt in Denim

Original Penguin Galway Guy L/S Shirt in Denim

$49.00$98.00

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This stylish long-sleeve from Original Penguin is a classic. Featuring a soft, chambray fabrication, the shirt's button-up construction promises a simple and effortless look. Detailed with front chest pocket and tab branding, the shirt will pair perfectly with your favourite dark denim and grey blazer for a semi-casual evening look.

Also available in store at Roadtrip.

100% Cotton

Heritage Slim Fit

Mini Collar

Machine Washable



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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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