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“Looking good isn’t important, it’s everything”.

In 1963 Ben Sherman began producing his iconic shirts from a small factory in Brighton to the soundtrack of The Beatles, The Troggs and The Kinks. From the tailored button downs, pique polos and graphic tees, the line embodies the mod movement that inspired it and combines music and style in perfect synchronicity.


Quick View Ben Sherman London Calling T-Shirt in Oat Ben Sherman London Calling T-Shirt in Oat Ben Sherman London Calling T-Shirt in Oat $58.00

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Ben Sherman London Calling T-Shirt in Oat

Ben Sherman London Calling T-Shirt in Oat

$58.00

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A man can never have too many graphic tees and this one from Ben Sherman is the perfect addition to your collection. Inspired by the Ben Sherman brand heritage, this vintage-looking target tee is just bold enough without being in-your-face bold. A classic, modern fit and soft cotton fabrication means this tee is just as comfortable as it is stylish. So what's holding you back? Hit the mark every time and pair this tee with jeans and a hoodie for a cool and casual look or throw it on with khaki shorts and hit the beach bar!

This Tee is also available in Other Colors.

Also available in store at Trustfund.

100% Cotton

Machine Wash Cold


Quick View Ben Sherman London Calling T-Shirt in Blue Ben Sherman London Calling T-Shirt in Blue Ben Sherman London Calling T-Shirt in Blue $58.00

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Ben Sherman London Calling T-Shirt in Blue

Ben Sherman London Calling T-Shirt in Blue

$58.00

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A man can never have too many graphic tees and this one from Ben Sherman is the perfect addition to your collection. Inspired by the Ben Sherman brand heritage, this vintage-looking target tee is just bold enough without being in-your-face bold. A classic, modern fit and soft cotton fabrication means this tee is just as comfortable as it is stylish. So what's holding you back? Hit the mark every time and pair this tee with jeans and a hoodie for a cool and casual look or throw it on with khaki shorts and hit the beach bar!

This Tee is also available in Other Colors.

Also available in store at Trustfund.

100% Cotton

Machine Wash Cold


Quick View Ben Sherman Lasting Moment L/S Shirt in Pink Ben Sherman Lasting Moment L/S Shirt in Pink Ben Sherman Lasting Moment L/S Shirt in Pink $108.00

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Ben Sherman Lasting Moment L/S Shirt in Pink

Ben Sherman Lasting Moment L/S Shirt in Pink

$108.00

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Check off classic plaid from your must-have list with this great button-up from Ben Sherman. Boasting an adjustable single cuff and two finger button-down collar, the shirt promises a sleek and polished look. Its mod fit guarantees total comfort, topped off with bias check on its pocket and back yoke for the perfect touch of detailing. Pair with dark denim and a grey cardigan for a sophisticated, casual look.

This shirt is available in Other Colors.

Also available in store at Roadtrip.

100% Cotton

Branded Spade Pocket

Machine Wash


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

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Ben Sherman Rewind L/S Shirt in Navy

Ben Sherman Rewind L/S Shirt in Navy

$118.00

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If there's one thing girls love it's a plaid boy. This bold plaid button down from Ben Sherman is exactly what you need to achieve that status. Featuring a two finger button down collar and a branded front pocket, this classic checked plaid long sleeve is perfect for throwing on with khakis and a dress shoe for an understated work look. Alternatively, you can roll up the sleeves and rock this plaid boy with topsiders and jean shorts.

Also available in store at Trustfund.

Regular Mod Fit

100% Cotton

Machine Washable


Quick View Ben Sherman Kentucky Bourbon L/S Shirt in Burnt Ben Sherman Kentucky Bourbon L/S Shirt in Burnt Ben Sherman Kentucky Bourbon L/S Shirt in Burnt $108.00

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Ben Sherman Kentucky Bourbon L/S Shirt in Burnt

Ben Sherman Kentucky Bourbon L/S Shirt in Burnt

$108.00

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A simple yet intricate plaid pattern is just one of the things we love about this button-down from Ben Sherman. That and its classic cut and button-down collar, of course! Cut from a premium cotton, this easy-to-wear staple looks great paired with a navy suit for your next job interview or unbuttoned over a white crew neck tee to get that boy-next-door look!

This Style from Ben Sherman is also available in Other Colors

Also available in store at Trustfund.

100% Cotton

Machine Washable


Quick View Ben Sherman Northern Rye Tee in Grey Ben Sherman Northern Rye Tee in Grey Ben Sherman Northern Rye Tee in Grey $68.00

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Ben Sherman Northern Rye Tee in Grey

Ben Sherman Northern Rye Tee in Grey

$68.00

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Walk the line between handsome and ruggedly casual in this classic Breton stripe tee from Ben Sherman. Cut from an ultra-soft cotton and outfitted with a classic spade pocket with contrast tipping, this tee showcases how a classic can still be contemporary. I you're pressed for time in the morning, simply throw this tee on with jeans and let the stripes do the talking!

This Tee is also available in Other Colors.

Also available in store at Roadtrip.

100% Cotton

Machine Washable


Quick View Ben Sherman Our City L/S Shirt in White Ben Sherman Our City L/S Shirt in White Ben Sherman Our City L/S Shirt in White $118.00

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Ben Sherman Our City L/S Shirt in White

Ben Sherman Our City L/S Shirt in White

$118.00

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It doesn't get much cooler than a sleek grid print button-down and Ben Sherman really nails it with the Our City long-sleeve shirt. While the straight cut and classic details show its timeless side, an ultra modern grid print really brings it into today's fashion scene. For and effortlessly cool look, throw this shirt on with black, slim-fit jeans and a leather jacket or wear it under a grey suit for an understated work outfit!

This Shirt is also available in Other Colors.

Also available in store at Roadtrip

100% Cotton

Machine Washable


Quick View Ben Sherman Our City L/S Shirt in Navy Ben Sherman Our City L/S Shirt in Navy Ben Sherman Our City L/S Shirt in Navy $118.00

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Ben Sherman Our City L/S Shirt in Navy

Ben Sherman Our City L/S Shirt in Navy

$118.00

View all product details

It doesn't get much cooler than a sleek grid print button-down and Ben Sherman really nails it with the Our City long-sleeve shirt. While the straight cut and classic details show its timeless side, an ultra modern grid print really brings it into today's fashion scene. For and effortlessly cool look, throw this shirt on with black, slim-fit jeans and a leather jacket or wear it under a grey suit for an understated work outfit!

This Shirt is also available in Other Colors.

Also available in store at Roadtrip

100% Cotton

Machine Washable


Quick View Ben Sherman Scottish Barrel L/S Shirt in Blue Ben Sherman Scottish Barrel L/S Shirt in Blue Ben Sherman Scottish Barrel L/S Shirt in Blue $138.00

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Ben Sherman Scottish Barrel L/S Shirt in Blue

Ben Sherman Scottish Barrel L/S Shirt in Blue

$138.00

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Inspired by their humble beginnings, Ben Sherman has created a shirt that truly stands the test of time. The 70's heritage plaid shirt strikes the perfect balance between timeless and modern without looking like you stole your grandpa's look. A classic cut and back box-pleat make this shirt an easy choice for throwing on with black jeans for drinks with coworkers or under a chunky cardigan for Sunday brunch!

Also available in store at Roadtrip.

100% Cotton

Machine Washable


Quick View Ben Sherman From Barley Shirt in Blue Ben Sherman From Barley Shirt in Blue Ben Sherman From Barley Shirt in Blue $118.00

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Ben Sherman From Barley Shirt in Blue

Ben Sherman From Barley Shirt in Blue

$118.00

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If you're tired of the same plain blue button-down Ben Sherman has your back (literally). This geometric micro check shirt has just the right amount of detail to add interest to your wardrobe without looking busy. Featuring a front spade pocket and a two finger button down collar as well as a back box pleat, this shirt has the makings of a classic. Wear it with grey suit pants and a silver tie for a sleek office look!

This Shirt is also available in Other Colors

Also available in store at Roadtrip.

100% Cotton

Machine Washable


Quick View Ben Sherman Headlines S/S Shirt in Berry Ben Sherman Headlines S/S Shirt in Berry Ben Sherman Headlines S/S Shirt in Berry $98.00

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Ben Sherman Headlines S/S Shirt in Berry

Ben Sherman Headlines S/S Shirt in Berry

$98.00

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Re-imagine an iconic gingham print without reinventing the wheel in this classic short sleeve button-down from Ben Sherman. A standard fit and one finger button-down help to balance the colourful contemporary print and a v-cut sleeve detail gives this shirt a fun twist. Pair this shirt with dark jeans for a casual day-time look or throw a bomber jacket on over top to up the cool factor for night time!

Also available in store at Trustfund.

100% Cotton

Machine Washable


Quick View Ben Sherman Oak Barrels Polo in Red Ben Sherman Oak Barrels Polo in Red Ben Sherman Oak Barrels Polo in Red $98.00

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Ben Sherman Oak Barrels Polo in Red

Ben Sherman Oak Barrels Polo in Red

$98.00

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Be the life of the party in this patterned polo from Ben Sherman. Its micro geo print is both fun and smart at the same time while keeping a casual vibe. A versatile piece, this polo features a three button placket, ribbed collar and cuffs and a classic spade pocket so you can still have that classic polo feel. Pair it with comfortable shorts for a weekend getaway or rock it with denim on a casual Friday!

This Polo is also available in Other Colors.

Also available in store at Roadtrip.

100% Cotton

Machine Washable


Quick View Ben Sherman Northern Rye Tee in Cream Ben Sherman Northern Rye Tee in Cream Ben Sherman Northern Rye Tee in Cream $68.00

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Ben Sherman Northern Rye Tee in Cream

Ben Sherman Northern Rye Tee in Cream

$68.00

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Walk the line between handsome and ruggedly casual in this classic Breton stripe tee from Ben Sherman. Cut from an ultra-soft cotton and outfitted with a classic spade pocket with contrast tipping, this tee showcases how a classic can still be contemporary. I you're pressed for time in the morning, simply throw this tee on with jeans and let the stripes do the talking!

This Tee is also available in Other Colors.

Also available in store at Roadtrip.

100% Cotton

Machine Washable


Quick View Ben Sherman Oak Barrels Polo in White Ben Sherman Oak Barrels Polo in White Ben Sherman Oak Barrels Polo in White $98.00

Added to Your Tote!

Ben Sherman Oak Barrels Polo in White

Ben Sherman Oak Barrels Polo in White

$98.00

View all product details

Be the life of the party in this patterned polo from Ben Sherman. Its micro geo print is both fun and smart at the same time while keeping a casual vibe. A versatile piece, this polo features a three button placket, ribbed collar and cuffs and a classic spade pocket so you can still have that classic polo feel. Pair it with comfortable shorts for a weekend getaway or rock it with denim on a casual Friday!

This Polo is also available in Other Colors.

Also available in store at Roadtrip.

100% Cotton

Machine Washable


Quick View Ben Sherman Smoky Oak Shirt in Grey Ben Sherman Smoky Oak Shirt in Grey Ben Sherman Smoky Oak Shirt in Grey $118.00

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Ben Sherman Smoky Oak Shirt in Grey

Ben Sherman Smoky Oak Shirt in Grey

$118.00

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Meet the coolest two tone texture shirt in the game from Ben Sherman. Crafted from a soft cotton and cut to a classic fit, this shirt was made for the cool-guy in you. Featuring a simple two finger button-down collar and tab branded chest pocket, this shirt is easy to throw on with black jeans for a refined evening out with friends. You can also wear it under a blazer for your next work presentation!

Also available in store at Roadtrip.

100% Cotton

Machine Washable


Quick View Ben Sherman Northern Rye Tee in Navy Ben Sherman Northern Rye Tee in Navy Ben Sherman Northern Rye Tee in Navy $68.00

Added to Your Tote!

Ben Sherman Northern Rye Tee in Navy

Ben Sherman Northern Rye Tee in Navy

$68.00

View all product details

Walk the line between handsome and ruggedly casual in this classic Breton stripe tee from Ben Sherman. Cut from an ultra-soft cotton and outfitted with a classic spade pocket with contrast tipping, this tee showcases how a classic can still be contemporary. I you're pressed for time in the morning, simply throw this tee on with jeans and let the stripes do the talking!

This Tee is also available in Other Colors.

Also available in store at Roadtrip.

100% Cotton

Machine Washable


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

Added to Your Tote!

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 Roadtrip.

100% Cotton

Machine Washable


Quick View Ben Sherman Single Malt L/S Shirt in Tartan Ben Sherman Single Malt L/S Shirt in Tartan Ben Sherman Single Malt L/S Shirt in Tartan $118.00

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Ben Sherman Single Malt L/S Shirt in Tartan

Ben Sherman Single Malt L/S Shirt in Tartan

$118.00

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Neither too bold nor too boring, Ben Sherman presents a modern take on a tartan shirt. Made from soft cotton and cut in a classic fit, this shirt showcases a simple two finger button-down collar and a branded chest pocket for a polished look. Keep it casual with black jeans and cozy cardigan or tuck it in to chinos and rock a briefcase with it to work!

Also available in store at Roadtrip.

100% Cotton

Machine Washable


Quick View Ben Sherman From Barley Shirt in White Ben Sherman From Barley Shirt in White Ben Sherman From Barley Shirt in White $118.00

Added to Your Tote!

Ben Sherman From Barley Shirt in White

Ben Sherman From Barley Shirt in White

$118.00

View all product details

If you're tired of the same plain white button-down Ben Sherman has your back (literally). This geometric micro check shirt has just the right amount of detail to add interest to your wardrobe without looking busy. Featuring a front spade pocket and a two finger button down collar as well as a back box pleat, this shirt has the makings of a classic. Wear it with grey suit pants and a silver tie for a sleek office look!

This Shirt is also available in Other Colors

Also available in store at Roadtrip.

100% Cotton

Machine Washable


Quick View Ben Sherman Border Crossing Polo in Green Ben Sherman Border Crossing Polo in Green Ben Sherman Border Crossing Polo in Green $49.00$78.00

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Ben Sherman Border Crossing Polo in Green

Ben Sherman Border Crossing Polo in Green

$49.00$78.00

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A pique polo is an iconic piece that every man needs in his roster. This polo will serve you well in almost any situation, be it a casual lunch meeting or a golf tournament. Contrasting tipping on the collar and sleeves gives a refined and modern feel to this classic polo while bold branding on the chest keeps you looking sharp. Pair this polo with printed shorts or throw it on with slacks at work!

This Polo is also available in Other Colors.

Also available in store at Trustfund.

100% Cotton

Machine Wash Cold


Quick View Ben Sherman Border Crossing Polo in Red Ben Sherman Border Crossing Polo in Red Ben Sherman Border Crossing Polo in Red $49.00$78.00

Added to Your Tote!

Ben Sherman Border Crossing Polo in Red

Ben Sherman Border Crossing Polo in Red

$49.00$78.00

View all product details

A pique polo is an iconic piece that every man needs in his roster. This polo will serve you well in almost any situation, be it a casual lunch meeting or a golf tournament. Contrasting tipping on the collar and sleeves gives a refined and modern feel to this classic polo while bold branding on the chest keeps you looking sharp. Pair this polo with printed shorts or throw it on with slacks at work!

This Polo is also available in Other Colors.

Also available in store at Trustfund.

100% Cotton

Machine Wash Cold


Quick View Ben Sherman Border Crossing Polo in Pink Ben Sherman Border Crossing Polo in Pink Ben Sherman Border Crossing Polo in Pink $49.00$78.00

Added to Your Tote!

Ben Sherman Border Crossing Polo in Pink

Ben Sherman Border Crossing Polo in Pink

$49.00$78.00

View all product details

A pique polo is an iconic piece that every man needs in his roster. This polo will serve you well in almost any situation, be it a casual lunch meeting or a golf tournament. Contrasting tipping on the collar and sleeves gives a refined and modern feel to this classic polo while bold branding on the chest keeps you looking sharp. Pair this polo with printed shorts or throw it on with slacks at work!

This Polo is also available in Other Colors.

Also available in store at Trustfund.

100% Cotton

Machine Wash Cold


Quick View Ben Sherman Border Crossing Polo in White Ben Sherman Border Crossing Polo in White Ben Sherman Border Crossing Polo in White $49.00$78.00

Added to Your Tote!

Ben Sherman Border Crossing Polo in White

Ben Sherman Border Crossing Polo in White

$49.00$78.00

View all product details

A pique polo is an iconic piece that every man needs in his roster. This polo will serve you well in almost any situation, be it a casual lunch meeting or a golf tournament. Contrasting tipping on the collar and sleeves gives a refined and modern feel to this classic polo while bold branding on the chest keeps you looking sharp. Pair this polo with printed shorts or throw it on with slacks at work!

This Polo is also available in Other Colors.

Also available in store at Trustfund.

100% Cotton

Machine Wash Cold


Quick View Ben Sherman On the Mend S/S Shirt in Blue Ben Sherman On the Mend S/S Shirt in Blue Ben Sherman On the Mend S/S Shirt in Blue $69.00$98.00

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Ben Sherman On the Mend S/S Shirt in Blue

Ben Sherman On the Mend S/S Shirt in Blue

$69.00$98.00

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Love gingham? This time around, Ben Sherman has taken this classic print and given it a modern update. Complete with a two finger button down collar and classic spade pocket, this shirt will instantly become your go-to, lightweight button-down. Team it with black jeans for a minimal look or throw it on over a white tee, unbuttoned and be effortlessly cool!

Also available in store at Trustfund.

100% Cotton

Machine Wash Cold


Quick View Ben Sherman Guelph S/S Shirt in Blue Ben Sherman Guelph S/S Shirt in Blue Ben Sherman Guelph S/S Shirt in Blue $69.00$118.00

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Ben Sherman Guelph S/S Shirt in Blue

Ben Sherman Guelph S/S Shirt in Blue

$69.00$118.00

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Something about linen just gives any outfit an effortless, easy-going feel and his gingham short-sleeve linen shirt from Ben Sherman is the perfect example. A classic and crisp gingham is offset by the casual linen fabrication to create the perfect everyday shirt. Featuring a two finger button-down collar, a back box pleat and our traditional tab branded chest pocket, this shirt is a truly iconic transition piece. Pair it with khakis, rolled at the bottom, for a sleek look.

Also available in store at Roadtrip.

55% Linen, 45% Cotton

Machine Wash Cold


Quick View Ben Sherman High Tide Shorts in Olive Ben Sherman High Tide Shorts in Olive Ben Sherman High Tide Shorts in Olive $69.00$98.00

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Ben Sherman High Tide Shorts in Olive

Ben Sherman High Tide Shorts in Olive

$69.00$98.00

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Transition without a hitch into warmer weather wearing these stretch chino shorts from Ben Sherman. A classic rolled cuff creates a perfect length: not too long, not too short, and a slim fit gives these shorts a modern feel. For the man who thinks comfort is key, these shorts will be a major winner. Make outfits easy, pairing these shorts with a striped tee or classic piqued polo for a casual cool look!

These Shorts are also available in Other Colors.

Also available in store at Roadtrip.

97% Cotton, 3% Elastane

Machine Washable


Quick View Ben Sherman High Tide Shorts in Black Ben Sherman High Tide Shorts in Black Ben Sherman High Tide Shorts in Black $69.00$98.00

Added to Your Tote!

Ben Sherman High Tide Shorts in Black

Ben Sherman High Tide Shorts in Black

$69.00$98.00

View all product details

Transition without a hitch into warmer weather wearing these stretch chino shorts from Ben Sherman. A classic rolled cuff creates a perfect length: not too long, not too short, and a slim fit gives these shorts a modern feel. For the man who thinks comfort is key, these shorts will be a major winner. Make outfits easy, pairing these shorts with a striped tee or classic piqued polo for a casual cool look!

These Shorts are also available in Other Colors.

Also available in store at Roadtrip.

97% Cotton, 3% Elastane

Machine Washable


Quick View Ben Sherman High Tide Shorts in Grey Ben Sherman High Tide Shorts in Grey Ben Sherman High Tide Shorts in Grey $69.00$98.00

Added to Your Tote!

Ben Sherman High Tide Shorts in Grey

Ben Sherman High Tide Shorts in Grey

$69.00$98.00

View all product details

Transition without a hitch into warmer weather wearing these stretch chino shorts from Ben Sherman. A classic rolled cuff creates a perfect length: not too long, not too short, and a slim fit gives these shorts a modern feel. For the man who thinks comfort is key, these shorts will be a major winner. Make outfits easy, pairing these shorts with a striped tee or classic piqued polo for a casual cool look!

These Shorts are also available in Other Colors.

Also available in store at Roadtrip.

97% Cotton, 3% Elastane

Machine Washable


Quick View Ben Sherman Rewind L/S Shirt in Sunset Ben Sherman Rewind L/S Shirt in Sunset Ben Sherman Rewind L/S Shirt in Sunset $79.00$118.00

Added to Your Tote!

Ben Sherman Rewind L/S Shirt in Sunset

Ben Sherman Rewind L/S Shirt in Sunset

$79.00$118.00

View all product details

If there's one thing girls love it's a plaid boy. This bold plaid button down from Ben Sherman is exactly what you need to achieve that status. Featuring a two finger button down collar and a branded front pocket, this classic checked plaid long sleeve is perfect for throwing on with khakis and a dress shoe for an understated work look. Alternatively, you can roll up the sleeves and rock this plaid boy with topsiders and jean shorts.

Also available in store at Roadtrip.

Regular Mod Fit

100% Cotton

Machine Washable


Quick View Ben Sherman Rewind L/S Shirt in Sky Ben Sherman Rewind L/S Shirt in Sky Ben Sherman Rewind L/S Shirt in Sky $79.00$118.00

Added to Your Tote!

Ben Sherman Rewind L/S Shirt in Sky

Ben Sherman Rewind L/S Shirt in Sky

$79.00$118.00

View all product details

If there's one thing girls love it's a plaid boy. This bold plaid button down from Ben Sherman is exactly what you need to achieve that status. Featuring a two finger button down collar and a branded front pocket, this classic checked plaid long sleeve is perfect for throwing on with khakis and a dress shoe for an understated work look. Alternatively, you can roll up the sleeves and rock this plaid boy with topsiders and jean shorts.

Also available in store at Roadtrip.

Regular Mod Fit

100% Cotton

Machine Washable


Quick View Ben Sherman Kentucky Bourbon L/S Shirt in Red Ben Sherman Kentucky Bourbon L/S Shirt in Red Ben Sherman Kentucky Bourbon L/S Shirt in Red $79.00$108.00

Added to Your Tote!

Ben Sherman Kentucky Bourbon L/S Shirt in Red

Ben Sherman Kentucky Bourbon L/S Shirt in Red

$79.00$108.00

View all product details

A simple yet intricate plaid pattern is just one of the things we love about this button-down from Ben Sherman. That and its classic cut and button-down collar, of course! Cut from a premium cotton, this easy-to-wear staple looks great paired with a navy suit for your next job interview or unbuttoned over a white crew neck tee to get that boy-next-door look!

This Style from Ben Sherman is also available in Other Colors

Also available in store at Roadtrip.

100% Cotton

Machine Washable


Quick View Ben Sherman Call On Me S/S Shirt in Green Ben Sherman Call On Me S/S Shirt in Green Ben Sherman Call On Me S/S Shirt in Green $69.00$98.00

Added to Your Tote!

Ben Sherman Call On Me S/S Shirt in Green

Ben Sherman Call On Me S/S Shirt in Green

$69.00$98.00

View all product details

It's really hard not to love short sleeve button downs and Ben Sherman makes it even harder with this endlessly classic gingham shirt. A modern yet iconic fit gives a sleek look without being restrictive while a two-finger button-down collar shows this shirt's more sophisticated side. Nobody will know you're rocking short sleeves when you pair this button-down with a navy blazer at work but you can also don this classic piece on weekends with khaki shorts!

Also available in store at Trustfund.

100% Cotton

Machine Washable


Page: 12

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