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Quick View Ben Sherman Karlito L/S Shirt in B/W Ben Sherman Karlito L/S Shirt in B/W Ben Sherman Karlito L/S Shirt in B/W $98.00

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Ben Sherman Karlito L/S Shirt in B/W

Ben Sherman Karlito L/S Shirt in B/W

$98.00

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Cut and styled for year round comfort, this cotton button down is the ideal staple. Sporting Ben Sherman's iconic gingham print, the Karlito features a classic two finger button down collar, side tab branding on the chest pocket, and a back box-pleat and locker-loop. In a regular modern fit, this shirt offers a polished and professional look. Style it with pants and leather shoes for the office, or with tan chinos and rolled sleeves for a more relaxed look.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


Quick View Ben Sherman Karlito L/S Shirt in Cocoa Ben Sherman Karlito L/S Shirt in Cocoa Ben Sherman Karlito L/S Shirt in Cocoa $98.00

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Ben Sherman Karlito L/S Shirt in Cocoa

Ben Sherman Karlito L/S Shirt in Cocoa

$98.00

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Cut and styled for year round comfort, this cotton button down is the ideal staple. Sporting Ben Sherman's iconic gingham print, the Karlito features a classic two finger button down collar, side tab branding on the chest pocket, and a back box-pleat and locker-loop. In a regular modern fit, this shirt offers a polished and professional look. Style it with pants and leather shoes for the office, or with tan chinos and rolled sleeves for a more relaxed look.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


Quick View Ben Sherman Karlito L/S Shirt in Cobalt Ben Sherman Karlito L/S Shirt in Cobalt Ben Sherman Karlito L/S Shirt in Cobalt $98.00

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Ben Sherman Karlito L/S Shirt in Cobalt

Ben Sherman Karlito L/S Shirt in Cobalt

$98.00

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Cut and styled for year round comfort, this cotton button down is the ideal staple. Sporting Ben Sherman's iconic gingham print, the Karlito features a classic two finger button down collar, side tab branding on the chest pocket, and a back box-pleat and locker-loop. In a regular modern fit, this shirt offers a polished and professional look. Style it with pants and leather shoes for the office, or with tan chinos and rolled sleeves for a more relaxed look.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


Quick View Ben Sherman Karlito L/S Shirt in Indigo Ben Sherman Karlito L/S Shirt in Indigo Ben Sherman Karlito L/S Shirt in Indigo $98.00

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Ben Sherman Karlito L/S Shirt in Indigo

Ben Sherman Karlito L/S Shirt in Indigo

$98.00

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Cut and styled for year round comfort, this cotton button down is the ideal staple. Sporting Ben Sherman's iconic gingham print, the Karlito features a classic two finger button down collar, side tab branding on the chest pocket, and a back box-pleat and locker-loop. In a regular modern fit, this shirt offers a polished and professional look. Style it with pants and leather shoes for the office, or with tan chinos and rolled sleeves for a more relaxed look.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


Quick View Ben Sherman Rayburn L/S Shirt in Red Ben Sherman Rayburn L/S Shirt in Red Ben Sherman Rayburn L/S Shirt in Red $98.00

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Ben Sherman Rayburn L/S Shirt in Red

Ben Sherman Rayburn L/S Shirt in Red

$98.00

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This shirt is a modern classic. Cut from a lightweight checkered cotton, it features a two finger button down collar and a tab branded chest pocket. Pair this shirt with tan chinos and leather boat shoes for the perfect weekend look.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


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

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Original Penguin Lynel L/S Shirt in Navy

Original Penguin Lynel L/S Shirt in Navy

$99.00

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The Lynel is crafted from a durable plain weave cotton fabric, that offers breathable comfort and just the right amount of stretch. In a versatile slim fit with a button down collar, this fun geometric shirt balances casual and polished perfectly. Wear yours to the office belted into dark grey chinos, or wear it on the weekend with rolled sleeves and leather boots.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


Quick View Original Penguin Haworth Polo in Night Original Penguin Haworth Polo in Night Original Penguin Haworth Polo in Night $79.00

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Original Penguin Haworth Polo in Night

Original Penguin Haworth Polo in Night

$79.00

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Always a sophisticated style, this pique polo from Original Penguin is a sharp staple to complete your collection. Crafted from lightweight cotton, and featuring ribbed cuffs and collar with contrast tipping, this refined piece is comfortably textured with a sleek pop of colour. A feel good fit on and off the clock, this birdseye knit fabric looks as great with faded denim and sneakers as it does with brown chinos and loafers.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


Quick View Matinique Boston L/S Shirt in Navy Matinique Boston L/S Shirt in Navy Matinique Boston L/S Shirt in Navy $109.00

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Matinique Boston L/S Shirt in Navy

Matinique Boston L/S Shirt in Navy

$109.00

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The Boston is a long sleeve button down that features a mini geometric print that is easily dressed up or down. Cut to a regular fit and crafted from soft and breathable cotton, this piece gives all day comfort. A definite staple for the office, try it on the weekend with rolled sleeves and brown boots.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

100% Cotton

Machine Washable


Quick View Matinique Venice L/S Shirt in Vert Matinique Venice L/S Shirt in Vert Matinique Venice L/S Shirt in Vert $99.00

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Matinique Venice L/S Shirt in Vert

Matinique Venice L/S Shirt in Vert

$99.00

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The Venice Shirt offers a contemporary twist to a polished and professional staple. A button down collar takes this piece effortlessly from work to play, and the breathable, soft cotton ensures all day comfort. Wear yours belted into dark  denim for a charming laid-back look.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Inside Out


Quick View Matinique Marc L/S Shirt in Maroon Matinique Marc L/S Shirt in Maroon Matinique Marc L/S Shirt in Maroon $109.00

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Matinique Marc L/S Shirt in Maroon

Matinique Marc L/S Shirt in Maroon

$109.00

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Blending formal and casual for a true staple that works all week long! This shirt from Matinique is crafted from crisp cotton and features a charming geometric print. Tuck it into black pants and accent it with a tie for the work day, or roll the sleeves and swap the trousers for denim on the weekend.

Also available in store at Roadtrip.

100% Cotton

Machine Washable


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

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Original Penguin Maddox L/S Shirt in Blue

Original Penguin Maddox L/S Shirt in Blue

$99.00

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The Maddox features a versatile mini gingham print, full button down placket, and a button down collar to easily dress up or down no matter the occasion. A chest pocket sports the signature Penguin logo for effortless sophistication. Keep it simple with rolled sleeves and dark denim, or wear it to work with blue panta and dark brogues.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


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

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Original Penguin Adyn L/S Shirt in Blue

Original Penguin Adyn L/S Shirt in Blue

$99.00

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Go for a classic look in this staple from Original Penguin. This button down features a full placket and a button down collar ideal for dress down days. A chest pocket sporting the signature Penguin logo keeps this fun style suave and sophisticated from early morning coffee runs to weekend date nights. Tuck it into tan chinos and add a black belt for your next casual Friday.

Also available in store at Roadtrip

100% Cotton

Machine Wash Cold


Quick View Original Penguin Flamingo S/S Shirt in Blue Original Penguin Flamingo S/S Shirt in Blue Original Penguin Flamingo S/S Shirt in Blue $89.00

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Original Penguin Flamingo S/S Shirt in Blue

Original Penguin Flamingo S/S Shirt in Blue

$89.00

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Take the tropics with you no matter the weather with the Flamingo Shirt from Original Penguin. A short sleeve, electric blue button down that features an all over flamingos and floral print, this warm weather staple sports a chest pocket and a button down collar. Get in the vacation spirit year round with slim fit denim and white sneakers.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


Quick View Ben Sherman London Boy L/S in Navy Ben Sherman London Boy L/S in Navy Ben Sherman London Boy L/S in Navy $118.00

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Ben Sherman London Boy L/S in Navy

Ben Sherman London Boy L/S in Navy

$118.00

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In true Ben Sherman style, the London Boy is a classic button down with contemporary appeal. Crafted from 100% cotton, this breathable style comes equipped with a classic point concealed button down collar for a laid back kind of sophistication. Wear yours with a grey blazer and pants for a dashing look to take you from the office to date night.

Also available in store at Roadtrip.

100% Cotton

Machine Washable


Quick View Ben Sherman Kalen L/S Shirt in Camel Ben Sherman Kalen L/S Shirt in Camel Ben Sherman Kalen L/S Shirt in Camel $128.00

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Ben Sherman Kalen L/S Shirt in Camel

Ben Sherman Kalen L/S Shirt in Camel

$128.00

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This long sleeve button down from Ben Sherman is the versatile staple you've been needing. Featuring a neutral base with textured details to easily dress up or down. The Kalen is crafted from breathable, season spanning cotton in Ben Sherman's signature mod fit, and includes a two finger button down collar and mitered cuffs to add a formal touch. Finish off the look with black slacks and a black leather belt for classically tailored office style.

Also available in store at Roadtrip.

100% Cotton

Machine Washable.


Quick View Matinique Edmund Shirt in Navy Matinique Edmund Shirt in Navy Matinique Edmund Shirt in Navy $139.00

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Matinique Edmund Shirt in Navy

Matinique Edmund Shirt in Navy

$139.00

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This button-down from Matinique features a subtle floral print on a dark navy backdrop that makes it versatile and easy to style. Boasting a sophisticated collared neckline and a button lined placket this piece is perfect for the office. Cut for a relaxed fit and made of ultra-soft 100% cotton this piece will have you sailing through your work week with complete ease. Polish this look off with black trousers and your go-to watch.

Also available in store at Roadtrip.

Regular Fit

100% Cotton

Machine Washable


Quick View Original Penguin Charlie Check L/S in Navy Original Penguin Charlie Check L/S in Navy Original Penguin Charlie Check L/S in Navy $99.00

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Original Penguin Charlie Check L/S in Navy

Original Penguin Charlie Check L/S in Navy

$99.00

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A sophisticated style on and off the clock, the Charlie is a long sleeve shirt that can effortlessly be dressed up or down. Crafted from a soft cotton blend and featuring a full placket and button down collar, this style is designed in neutral blues to create a wardrobe staple for any occasion.

Also available in store at Roadtrip.

60% Cotton, 40% Polyester

Machine Wash Cold


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

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Original Penguin Paul Plaid L/S in Green

Original Penguin Paul Plaid L/S in Green

$99.00

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

This Style also comes in Other Colors.

Also available in store at Roadtrip.

Heritage Slim Fit

60% Cotton, 40% Polyester

Machine Wash Cold


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

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Original Penguin Paul Plaid L/S in Navy

Original Penguin Paul Plaid L/S in Navy

$99.00

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

This Style also comes in Other Colors.

Also available in store at Roadtrip.

Heritage Slim Fit

60% Cotton, 40% Polyester

Machine Wash Cold


Quick View Scotch & Soda Griffin Flannel L/S Shirt in Dusk Scotch & Soda Griffin Flannel L/S Shirt in Dusk $149.00

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Scotch & Soda Griffin Flannel L/S Shirt in Dusk

Scotch & Soda Griffin Flannel L/S Shirt in Dusk

$149.00

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Featuring a regular fit with an eye-catching multi-color pattern for days where you want to flaunt your stylish taste. The combination of the classic collar, chest pocket, and lightweight fabrication make this a comfortable piece that can easily be dressed up or down. Pair with black trousers and brown loafers for your 9-5 grind.

Also available in store at Trustfund.

65% Polyester, 35% Viscose

Machine Washable


Quick View Casual Friday Bergen L/S Shirt in Grey Casual Friday Bergen L/S Shirt in Grey Casual Friday Bergen L/S Shirt in Grey $89.00

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Casual Friday Bergen L/S Shirt in Grey

Casual Friday Bergen L/S Shirt in Grey

$89.00

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This button down is crafted from a soft cotton and cut in a slim fit. With a chest pocket and button down collar, the Bergen features neutral grey tones for truly timeless appeal.

Also available in store at Roadtrip.

100% Cotton

Machine Washable


Quick View Casual Friday Lund L/S Shirt in Blue Casual Friday Lund L/S Shirt in Blue Casual Friday Lund L/S Shirt in Blue $105.00

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Casual Friday Lund L/S Shirt in Blue

Casual Friday Lund L/S Shirt in Blue

$105.00

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The Lund shirt from Casual Friday is a modern take on a classic button down that takes you seamlessly from workday to weekend. Sporting a fresh all over starburst print and crafted from a lightweight cotton, this long sleeve is cut in a regular fit for all day comfort.

Also available in store at Roadtrip.

100% Cotton

Machine Washable


Quick View Casual Friday Odense L/S Shirt in Blue Casual Friday Odense L/S Shirt in Blue Casual Friday Odense L/S Shirt in Blue $89.00

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Casual Friday Odense L/S Shirt in Blue

Casual Friday Odense L/S Shirt in Blue

$89.00

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A shirt that fits easily into your daily wardrobe or weekend roster, the Odense is a long sleeve button down that's perfect for office casual. Crafted from a light and comfortable cotton and cut in a slim fit that never compromises movement. A simple staple for day and night, wear it year round with khaki chinos and leather sneakers.

Also available in store at Roadtrip.

100% Cotton

Machine Washable


Quick View Levi's Earl Chambray Shirt in Denim Levi's Earl Chambray Shirt in Denim Levi's Earl Chambray Shirt in Denim $89.00

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Levi's Earl Chambray Shirt in Denim

Levi's Earl Chambray Shirt in Denim

$89.00

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Whether it be a day at the office or a night on the town, this shirt has you covered. Fabricated from soft 100% cotton, this timeless piece promises you nothing but complete comfort. The button flap square pockets and double button cuffs make this piece easy to style whether you deice to keep it open or button it up. Style with black denim jeans and a white shirt underneath for a smart casual look.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


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

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Original Penguin Roger L/S Shirt in Navy

Original Penguin Roger L/S Shirt in Navy

$99.00

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Artfully textured, the Rodger Shirt from Original Penguin is a sleek classic that is ideal for day to night wear. This unique piece is crafted from cotton in a slim fit, and features woven and raised threads that create a contrasting check pattern. A stretch fabric that moves with your body offers an easy wear, while the button down collar keeps you looking sharp. Add a grey sports jacket for office attire, or pair with jeans and sneakers for after hours.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Wash Cold


Quick View Original Penguin Colin L/S Shirt Original Penguin Colin L/S Shirt Original Penguin Colin L/S Shirt $99.00

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Original Penguin Colin L/S Shirt

Original Penguin Colin L/S Shirt

$99.00

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A staple in any work week roster, this cotton button down is the coolest choice for all day comfort. With a subtle geometric pattern and a button down collar, you'll look polished and professional for every occasion. Cut in a slim fit to keep you looking sharp. Finish off the look with rolled sleeves and black jeans for your after hours wind down.

Also available in store at Roadtrip.

Heritage Slim Fit

100% Cotton

Machine Wash Cold


Quick View Original Penguin Haworth Polo in Wine Original Penguin Haworth Polo in Wine Original Penguin Haworth Polo in Wine $79.00

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Original Penguin Haworth Polo in Wine

Original Penguin Haworth Polo in Wine

$79.00

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Always a sophisticated style, this pique polo from Original Penguin is a sharp staple to complete your collection. Crafted from lightweight cotton, and featuring ribbed cuffs/collar with contrast tipping, this refined piece is comfortably textured with a sleek pop of colour. A feel good fit on and off the clock, this birdseye knit fabric looks as great with faded denim and sneakers as it does with brown chinos and loafers.

This Style is also available in Other Colors.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


Quick View Ben Sherman Patrick L/S Shirt in Forest Ben Sherman Patrick L/S Shirt in Forest Ben Sherman Patrick L/S Shirt in Forest $98.00

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Ben Sherman Patrick L/S Shirt in Forest

Ben Sherman Patrick L/S Shirt in Forest

$98.00

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This classic oxford from Ben Sherman is an instant favourite, cut from soft and breathable cotton in micro gingham print. In a regular mod fit, this essential shirt sports a front pocket, a two finger button down collar, and is made for easy wears and effortless styling. Tuck this long sleeve shirt into blue jeans and add a brown belt for a refreshing pop of pattern.

This Style is also available in Other Colors.

Also available in store at Trustfund.

100% Cotton Machine Washable


Quick View Scotch & Soda Checklist L/S Shirt in B/W Scotch & Soda Checklist L/S Shirt in B/W $149.00

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Scotch & Soda Checklist L/S Shirt in B/W

Scotch & Soda Checklist L/S Shirt in B/W

$149.00

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Check off all your button down needs with the Checklist Shirt. With soft woven cotton and a regular fit, this lightweight dress shirt keeps you cool and classic from day to night. A black and white check pattern, a collared neckline and a chest pocket bring to life this wardrobe staple. Pair it with chinos and black laced shoes for a truly timeless outfit.

Also available in store at Trustfund

Regular Fit

100% Cotton

Machine Wash Cold


Quick View Original Penguin Pete Polo in White Original Penguin Pete Polo in White Original Penguin Pete Polo in White $69.00

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Original Penguin Pete Polo in White

Original Penguin Pete Polo in White

$69.00

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Experts in classics, Original Penguin knows a thing or two about the polo game. Cut in the brand's signature heritage slim fit, this staple top is crafted from soft 100% cotton in a pique fabrication to add a unique textured appearance. The ribbed cuffs and collar with contrast tipping add a hint of sophistication, great for sporting with dark wash denim and a leather jacket.

This Style is also available in Other Colors.

Also available in store at Trustfund.

Slim Fit

100% Cotton

Machine Wash Cold


Quick View Matinique Maverick L/S Shirt in White Matinique Maverick L/S Shirt in White Matinique Maverick L/S Shirt in White $129.00

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Matinique Maverick L/S Shirt in White

Matinique Maverick L/S Shirt in White

$129.00

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Patterned shirts tend to be for the more confident set, but this subtle-floral print piece from Matinique is smart and wearable. Mini navy florals are set against a soft white background in a slim fit cut for the most dapper of looks. The stretch cotton material ensures comfort is never sacrificed here. Pair with navy suiting and brown leather brogues to add a point of interest!

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


Quick View Ben Sherman Benny L/S Shirt in Rust Ben Sherman Benny L/S Shirt in Rust Ben Sherman Benny L/S Shirt in Rust $98.00

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Ben Sherman Benny L/S Shirt in Rust

Ben Sherman Benny L/S Shirt in Rust

$98.00

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No one knows how to craft perfect versatile pieces quite like Ben Sherman. Cut for a modern fit, this top features a classic button down front, collared neckline and spade pocket on the chest. Pair with a khaki pant and brown loafer for a great 9-5 look.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Warm


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

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Original Penguin William Polo in Navy

Original Penguin William Polo in Navy

$65.00

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

This Style is also available in Other Colors.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


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

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Original Penguin William Polo in Black

Original Penguin William Polo in Black

$65.00

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

This Style is also available in Other Colors.

Also available in store at Roadtrip.

100% Cotton

Machine Wash Cold


Quick View Ben Sherman Scotch Neat L/S Shirt in Navy Ben Sherman Scotch Neat L/S Shirt in Navy Ben Sherman Scotch Neat L/S Shirt in Navy $118.00

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Ben Sherman Scotch Neat L/S Shirt in Navy

Ben Sherman Scotch Neat L/S Shirt in Navy

$118.00

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A good polka dot shirt is a timeless piece that will still make you stand out as a man with style! Cut in a classic fit with a back box pleat and hanger loop, this button down is finished with a minimal small point button down collar. Let the dots speak for themselves and pair this shirt with a pair of neutral trousers for an understated yet put-together outfit. Alternatively, this shirt looks great peaking out under a crew-neck sweater!

Also available in store at Trustfund.

100% Cotton

Machine Washable



We're Canadian

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


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

24-B York Street, Ottawa
Canada K1N 1K2
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613.562.0992