Timberland Mumford River Slim Fit Chambray Shirt

via timberland.com

Cool chambray shirt right? We thought so too, and were surprised by the retailer. Yes, Timberland. They are stepping up their garment game. The king of tan work boots has been branching out for a few years now, and they are really hitting a groove. Just in time for vacation season, this soft chambray shirt will be a key item to toss in your bag on your way to the beach. Perfect for tiki huts, no-shower happy hours, or even a nicer sit down dinner outside, this pocketed chambray long sleeve has some dynamic range. Its versatility and light weight construction makes this is a great "just-in-case" piece to take with you from now til October. It comes in blue and the "duck green." We've seen about a million blue chambrays, so we think the green is the way to go. We suggest pairing it with some tan shorts, deep indigo jeans, or black chinos, just keep away from the chambray shorts, no one likes a guy would has had too much chambray.

Available on Timberland.com for $55 

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Scotch and Soda Melange Oxford Shirt

via scotchandsoda.com

Every guy needs a good oxford. While this shouldn't be your first oxford shirt purchase, it is an awesome take on a closet classic. The white and melange (mixed) tan two-tone look is super summery, and what we will call upscale-beach bum. Paired with navy shorts or summer weight chinos, this shirt is the go-to for the twilight bar specials near the sand. This can also be a great top layer when paired with a tank or t-shirt, for a more versatile outfit choice for the days that last into the night.

Available on scotchandsoda.com for $115 

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Bonobos Pink Driftwoord Check Linen Shirt

via Bonobos.com

It's time to move your short-sleeve and lighter-weight button downs front and center in your closet. This is inevitably when you end up figuring out that some of the shirts you wore last year are either pit stained and battered, or no longer fit. So in order to get your summer look on, in threads that fit, we are suggesting this linen button down from Bonobos. It's not too loud, and goes with all of the blues, khakis, and browns you have in your closet. It goes great with khaki shorts, navy lightweight chinos, or a well-fitting pair of jeans. Toss on some brown drivers, and a nice pair of sunnies, and you are one cool cat.

 Available on Bonobos.com for $88

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San Matera Stretch-Cotton Camp Shirt

via TommyBahama.com

The beach is in our future. We can feel it! This means it is now prep time, and we are prepping by getting our Felix Leiter on (for those James Bond fans out there). Throwing on this 99% cotton, 1% spandex shirt is a one-way boat trip to coercing your brain into a spring and summer mentality, and when worn with a good pair of shades, and some slim fit khaki pants, you have a timeless, sophisticated look worthy of an immortalized CIA operative conveniently saving the world from the luxury of a beach town. 

Available on TommyBahama.com for $110 

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Frank and Oak Jasper Marled Button Down

via frankandoak.com

This marled button down from Frank and Oak is a great stand-alone piece that also functions as a stylish top layer when paired with a solid or graphic t-shirt underneath. The marled nature of the all cotton fabric gives the shirt a bit of heft and structure that you don't get with chambrays and other standard cotton button downs. This is the collared shirt for the casual office when the temperatures in the morning start in the 40s and look to rise into the 60s. It also transitions from work to play extremely well when worn with dark wash (or raw) jeans or even khaki or dark green chinos.

Available on FrankandOak.com for $60 

Full Disclaimer: By clicking "Buy" and purchasing an item from this retailer, we here at What is A Gentleman receive a commission to help keep this site running.

Taylrd Blue Flamingo Short Sleeve Button Down

via TaylrdClothing.com

Spring break is right around the corner, have you found your party shirt yet? If the answer is no, look no further than this awesome flamingo print short sleeve button from Taylrd Clothing. Take your peacocking to the beach and flamingo yourself all over the boardwalk with this 100% cotton party shirt. Make sure to check the fit guide to see whether you are slim or standard fit, and note the slim-fits have some tapering through the middle so if you have a bit of a pouch where you keep all your extra cookies, we'd suggest you go with the standard fit. Wear this with light-weight gray chinos, white chinos, khaki shorts, or a even a coral short if you are feeling particularly beachy. 

Available on taylrdclothing.com for $50 

Full Disclaimer: By clicking "Buy" and purchasing an item from this retailer, we here at What is A Gentleman do not receive a commission, we just really like flamingos!

Club Monaco Vintage Floral Button Down

via clubmonaco.com

A lightly-colored floral shirt for Fall? Seriously? Yes, seriously. Rules are made to be broken, and while the official timeframe to wear white has passed, we say, if you are confident enough to do away with the rules, you are confident enough to rock this floral button down from Club Monaco. It's 100% cotton with buttoned collars (always a plus for us) and has a breast pocket, just in case. This casual yet flashy top will go great under a muted colored cardigan or bomber, and a nice pair of corduroys or maroon chinos.

Available on clubmonaco.com for $80

Full Disclaimer: We don't make money off of this item, but we think it will serve you well.

Thought Dauber Spot Organic Cotton Shirt

If your eyes are feeling a little spotty from looking at the solar eclipse today, this shirt may get confusing. These spots are actually intended to be on this shirt as it is a Dauber Spot button down. This short sleeve casual shirt from Thought in the UK is made from 100% organic cotton, meaning it is responsibly sourced and its manufacturing had a minimal impact on the environment, so you can feel good about buying it and wearing it. The bottom of the shirt is a more straight cut, meaning it wasn't made to tuck so if you are a tucker this one isn't for you. We suggest you wear this with dark color chinos or jeans to balance out the white.

Available on sale at wearethought.com for $42 with shipping price included (on sale from $58)

Ted Back Drakey Diamond Print Shirt

They say diamonds are a girl's best friend, and these diamonds can be yours for at least the next 2 months. This casual button down from Ted Baker is designed to be untucked with a straighter hem around the waist and is made from 100% Lyocell, which is a more expensive semi-synthetic material that feels somewhere between cotton and silk and is wrinkle resistant and machine washable. The diamond pattern is just bold enough to be interesting but not overpowering making it perfect for date night or a weeknight out when paired with some solid chinos or khaki shorts.

Available on sale at TedBaker.com for $59 (on sale from $150)

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J.Crew Short Sleeve Dobby Button Down

As we hit the second half of summer, chances are you've worn through your set of short sleeves via to your weekly outdoor drinking outings, outside concerts, and date nights. This means it's time to refresh the set and add some new blood to the closet. This dobby short sleeve from J.crew is a great late off-the-bench addition to your summertime lineup because of its interesting color (we likened it to the beige version of purple) and subtle pop of pattern. Wear this interesting-colored top with your dark wash skinny jeans, gray summer weight chinos, or a pair of clean khaki shorts. Get it quickly, because it's only on sale until tonight!

Available on Factory.Jcrew.com for $39 (on sale from $65)

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Bonobos Banana Print Button Down Shirt

Summer is the season to have fun, some would even say it's the season to.......go bananas! (you're welcome). Bonobos is traditionally known for their wide selection of chinos, but have since widely expanded to the realm of all things men's clothing, with some tastefully bold designs along with some of the classics. This long sleeve button down is admittedly a bit goofy but does give off a playful vibe perfect for BBQs, and the casual day-long turned night time turn-up. Go ape in this banana splattered printed beauty and find yourself a worthy mate even if it is just for the night.

Available on Bonobos.com for $88

Full disclosure: By making a purchase after clicking "buy" we receive commission that helps this site grow.

Club Monaco Linen Check Button-Down

via clubmonaco.com

Days getting shorter across the northern hemisphere can only mean the nights are getting longer. With longer nights comes cooler temperatures, meaning that a long sleeve that keeps you cool in the humidity but covered when the temperature gets a little low, is critical. This linen long sleeve button down from Club Monaco is the perfectly adaptable top that can look great in the sun and at the late-night tiki bar. The button down collar keeps you from a flappy neck,  and the tailored fit isn't too tight meaning the breeze can get in to cool you down. We suggest you sport this top with some navy or khaki chinos, or solid colored shorts.

Available on sale at ClubMonaco.com for $49 (on sale from $120)

Full disclosure: By making a purchase after clicking "buy" we receive commission that helps this site grow.

Maker & Company Print Sport Shirt

via Nordstrom.com

Now that Memorial Day has passed, it is officially time for white shirts and short shorts. This lightweight 100% cotton short sleeve button-down is perfect for your long summer of outdoor activities with friends and family. This "overcast" shirt from Maker & Company is designed with a white fabric base with somewhat asymmetrical light gray vertical dashes to give it more character than your standard white shirt. What's even better, it is available at Nordstrom, which is having their half-yearly sale this week and this shirt is included, at 40% off! There are plenty of other shirts that are on sale but since it is now open season on wearing white, we felt this is the most appropriate.

Available on sale Nordstrom.com for $59 (normally $98)

Full disclosure: By making a purchase after clicking "buy" we receive commission that helps this site grow.

Hurley Montauk Woven Short Sleeve Button Down

via Nordstrom.com

Say goodbye to the days when rolling up your long sleeves was the only way to be comfortable in the summer while attempting to look stylish. Short sleeve button-downs are in, and in a big way.

You work hard, you deserve to show off the arms, look good, and feel relaxed during the hotter months of the year. This Montauk 100% cotton button-down from Hurley, yes the old Pac Sun staple, is perfect for a night out when the humidity is sitting close to 60% at 10 pm. The pattern here, FYI, is what can be described as "unfocused stars" or maybe "unfocused birds", either way, we like what we (can kind of) see. We suggest wearing this shirt with dark wash jeans, maybe a blue bomber jacket if the temperature permits, or medium gray chinos.

Available at Nordstrom.com for $50

Full disclosure: By making a purchase after clicking "buy" we receive commission that helps this site grow.

UNIQLO Linen Long Sleeve Shirt

As the weather heats up, you need a shirt that can keep you cool during the day but also covers you up at night. This long sleeve linen shirt from UNIQLO is a great lightweight shirt for your back yard booze fests, rooftop hangouts, and warm night excursions. It is made from 100% linen from France and has a looser fit, to keep you cool and flowing like your one-liners to the girls in those sun dresses. We suggest you wear these with khaki shorts in the daytime heat, dark wash jeans for a casual night out, or white chinos for your nighttime yacht parties.

Available on sale on UNIQLO.com right now for $20.

Full disclosure: By making a purchase after clicking "buy" we receive commission that helps this site grow.

1901 Hawaiian Embroidered Woven Shirt

Via Nordstrom.com

And the floral print selections continue! This awesome Hawaiian shirt from 1901 has great muted maroon coloring, a classic Hawaiian fern pattern, and great embroidered hula girls scattered throughout the shirt making it a unique spring button-down perfect for any outside drink activity. The shirt is dyed oxford cotton, meaning it will have some body and good structure and is armed with a button-down collar keeping the shape of the shirt around the neck so you don't have to worry about the collar tips turning into wings. We like this shirt with a solid color pair of shorts, chinos, or dark wash jeans and some shades like these.

Available on Nordstrom.com for $60

Full disclosure: By making a purchase after clicking "buy" we receive commission that helps this site grow.