How to Wear A Short Sleeve Button Down Shirt (Styled 5 Ways)11 min read

The short sleeve button up shirt is a summer essential that deserves to be in every man’s closet.

How to Wear A Short Sleeve Button Up Shirt (5 Shirts 5 Ways) | GENTLEMAN WITHIN

In this article I provide fashion inspiration and tips on how to wear a short sleeve button up (also button down) shirt with style so you can avoid looking like Dwight Scrhute from The Office.

I’m 5’6″ for reference and so all of these outfits are ideal for guys of shorter stature.


A few overarching tips before we start. It comes as no surprise, but above all, keep it simple. Summer is the ideal season for simple getups. And simple doesn’t mean boring either.

Remember that you’ll want to nail the fit. That means your sleeves fall at the appropriate length (mid-bicep), are nice and snug around your bicep, and a proper body length.

Spring & Summer Fashion Essentials for Men (Timeless Trends) | GENTLEMAN WITHINRelated: Check out this guide on Timeless Spring & Summer Fashion Essentials.

For untucked shirt length, the sweet spot is around mid-fly. An inch and a half or more longer, then you may want to tuck it in depending on the formality of the shirt. For example, I wouldn’t tuck in a floral shirt; however, a solid colored shirt is okay to tuck.

Finally, the shirt shouldn’t be skin tight. A little bit of breathing room is beneficial, especially in the summer heat. But you don’t want your shirt to be too loose either since a billowy muffin top isn’t flattering, especially with a short sleeved shirt.

How to Wear a Short Sleeve Button Up Shirt 6 Ways (Casual Outfit Ideas for Men)

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There’s a handful of short sleeve button up shirt styles that I mention in this article; namely madras, floral, two tone, micro print, and chambray.

I want to mention that every single article of clothing in the following outfits are interchangeable because of the neutral color schemes, and so you can mix and match these pieces as you see fit.

You’re gonna see a few pops of color here and there. Additions of accessories like watches, simple bracelets, and webbed cloth or canvas belts keep things interesting without overdoing it. And for footwear, I stick with low top, minimalist sneakers and loafers for casual, cool summertime vibes.

Without further ado, let’s get started on how to wear a short sleeve button up shirt starting with traditional madras.

1. The Madras Short Sleeve Shirt

Madras shirts are a casual summer staple. They’re lightweight, soft and colorful which provides a vibrant touch to any laid back summer look.

It’s a pattern distinguished by different colored checks and stripes that cross over each other. Madras has preppy undertones and is often mistaken for plaid, another check pattern.

Madras Outfit Accessories Details
WHAT I’M WEARING — Madras Shirt: Amazon Essentials | Linen Shorts: Amazon Essentials | Belt: Jukmo | Watch: Timex | Sunglasses: Warby Parker | Bracelet: RoseGold & Black | Cotton Pocket Square: CoCoUSM

Fun fact: Madras originated in a city in East India with the name of (you guessed it) Madras.

If you’re looking for a no frills, relaxed summer getup, madras is an excellent pattern to wear. See how I styled it below.

How to Wear a Madras Short Sleeve Shirt

The summer classic, madras is a fun pattern to wear. It looks like plaid and usually comes in vibrant colors that pair especially well with shorts.

In the first getup, I paired the blue, orange and white madras shirt with 100% linen shorts. Notice the wrinkles on the shorts. I feel that linen is one of the few fabrics that actually look better when it’s wrinkled. So let them crease and don’t worry too much.

With the second outfit, I made a simple swap of the linen shorts for a pair of olive green chino shorts. Just like the linen shorts, I rolled the chino shorts twice (double roll) for a nice taper around my thighs. Plus I think the shorts look good about 2-3 inches above the knees, wouldn’t you agree?

Madras Short Sleeve Button Down Shirt Outfit
WHAT I’M WEARING — Madras Shirt: Amazon Essentials | Linen Shorts: Amazon Essentials | Chino Shorts: Express | Huarache Sandals: Nisolo | Belt: Jukmo | Watch: Timex | Sunglasses: Warby Parker | Bracelet: RoseGold & Black | Cotton Pocket Square: CoCoUSM

For footwear, I went with a pair of tobacco brown huaraches from Nisolo. They’re all leather and wear like sandals, but are more dressy than a pair of Birkenstocks or flip flops, but still casual and works well with the overall look.

And now for the accessories, I’m wearing a beige webbed cloth belt that matches the overall casualness of the look. Then I picked a pair of blue acetate sunglasses from Warby Parker, a classic Timex Weekender and a blue beaded bracelet which all play harmoniously together. Finally, notice the white cotton pocket square in the right breast pocket that serves as a small accent detail and functions as a wipe cloth.

2. The Floral Short Sleeve Button Down Shirt

Floral shirts, aka tropical print shirts are easily distinguished by the flowers, plants or tropical trees printed on the shirt fabric. It’s the quintessential beach shirt, but it doesn’t mean you have to be near a large body of water to wear one.


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They come in all sorts of crazy colors and patterns, but one thing’s for sure it takes a little bit of confidence to pull it off. The hot weather of summer calls for an epic floral print, so be confident and own the look.

How to Wear A Floral Short Sleeve Button Down Shirt

It’s easy to go horribly wrong with floral shirts, but thankfully there are a few tips I have that if you keep in mind, will have you looking super stylish instead of super gaudy.

First, the floral print shirt will always be the main focus of this look. Tropical prints are typically bold to begin with and you don’t want other pieces competing for attention. Keep everything else that you’re wearing relatively subdued. Avoid wearing additional patterns or vibrant colors that might end up clashing with the floral shirt.

For the pants, I’m wearing light wash (dark wash jeans could work too) distressed denim with a fair amount of stretch. The distressing in this case is minimal and tasteful in my opinion. They’re not completely shredded and thus don’t draw too much attention, still giving the shirt the spotlight.

Floral Print Short Sleeve Button Down Shirt Outfit
WHAT I’M WEARING — Floral Shirt: Express | Slim Light Wash Jeans: Express | White Sneakers: Ace Marks | Watch: Timex | Sunglasses: Warby Parker | Bracelet: Bryer Leather

Additionally, I rolled up the sleeves for a snug fit around my bicep. And, of course I couldn’t forget the summer shades either. Again, they’re blue acetate Warby Parkers, one of my favorites to wear in the summer. Then for footwear, I went with classic white trainers from Ace Marks which can be worn with almost anything from suits to tropical shirts.

The watch I’m wearing is the Timex MK1 California in the blue colorway. Although it’s bold, I feel that it doesn’t clash due to being a smaller accessory. In this case it plays well with the tropical print. And finally, of late, I’ve been playing with wearing minimal bracelets on the same wrist as my watch for some added casual style.

3. The Two Tone Short Sleeve Shirt

A two tone shirt is basically any shirt with two distinct blocks of color dividing the shirt in half, usually horizontally. 

Two Tone Outfit Accessories Details
WHAT I’M WEARING — Two Tone Shirt: Sold Out | Navy Chinos: Everlane | Watch: Seiko | Sunglasses: Van Vliet | Pocket Square: Sprezzabox 

Two tone short sleeve button down shirts aren’t as common as the other shirts in this article, which make them a great pickup if you want your summer outfit to stand out from the crowd.

They’re usually divided into two similar shades for a monochrome and minimal aesthetic. Solid block colors are clean and simple and fairly easy to style. Take a look at the example below.

How to Wear A Two Tone Short Sleeve Shirt

You can rock the two tone short sleeve button down shirt either tucked in or untucked depending on the shirt’s length. If it hits at around mid-fly, that’s always a good length to wear untucked. Anything longer than that is a good length to tuck in.

Since the two tone shirt that I have is a little bit longer, I decided to tuck it in. Plus the slim navy chinos gives the look more of a smart casual, dressed up feeling, and so tucking in the shirt felt appropriate.

Two Tone Color Block Short Sleeve Button Down Shirt Outfit
WHAT I’M WEARING — Two Tone Shirt: Sold Out | Navy Chinos: Everlane | Gucci Bit Loafers: Cole Haan | Watch: Seiko | Sunglasses: Van Vliet | Pocket Square: Sprezzabox 

On my feet I’m wearing a pair of tan bit loafers. The brown (also called walnut or cognac) is the perfect shade for summer. Notice how there is no break on the chinos as the pants aren’t touching the shoes at all. It keeps things clean and streamlined. It’s no secret that loafers are an excellent summer shoe and looks especially sharp with slim, tapered pants with no break.

We can’t forget the accessories. I went with a pair of round lens, horn frame glasses. And for a quick wrist check, I’m wearing the military inspired Seiko 5 SNK803 field watch with a brown leather strap that complements the brown bracelet and bit loafers. And finally, I’m back at it again with the contrasting blue handkerchief for extra style and function.

4. The Chambray Short Sleeve Button Down Shirt

Chambray is a plain weave fabric usually made of cotton fibers. It’s like a more refined version of linen. They’re both inherently casually fabrics, but chambray typically has a tighter weave and can appear slightly dressier than linen. Also, chambray doesn’t wrinkle quite as much as linen either.

Chambray Short Sleeve Button Down Shirt Details

In terms of looks, chambray is similar in appearance to denim, but is much lighter and wears well in the summertime as opposed to thick denim. One thing’s for sure, a chambray shirt is a great hot weather fashion option not only because of its lightweight breathable fabric, but also for it’s casual vibes.

How To Wear A Chambray Short Sleeve Button Down Shirt

As mentioned above, chambray shirts have the look of a denim shirt, except it’s more lightweight and breathable which makes them a great option for warmer weather.

This look is a no frills, casual warm weather look. There’s a little bit of layering going on. Sometimes I like to unbutton my button down shirts for an ultra casual cool style.

Chambray Short Sleeve Button Down Shirt Outfit
WHAT I’M WEARING — Chambray Shirt: Amazon Essentials | White T-Shirt: Uniqlo | White Slim Jeans: Express (similar: Levi’s) | Sneakers: J.Crew Vans | Watch: Hamilton | Bracelet: RoseGold & Black | Pocket Square: Sold Out | No-Show Socks: FITS (20% off w/code GENTLEMAN) | Sneaker Balls: Sof Sole

The blue chambray shirt from Levi’s that I’m rocking has a bit of texture to it. I decided to layer it over top of a well fitting plain white t-shirt. Notice again, the linen pocket square in the right breast pocket. Here it not only serves as a stylish accessory, but also functions as a cloth to wipe sweat from my forehead if necessary.

For the pants I decided to go with a pair of slim fit white jeans from Express that has nice amount of stretch to it. On my feet are the classic canvas Vans in beige from J.Crew. I love these canvas sneakers for summer time. They’re casual, stylish and pairs really nicely with the unbuttoned shirt style. Don’t forget these sneaker balls to keep your shoes fresh all summer long.

Finally, a quick wrist check; I’m wearing an olive Hamilton Khaki Field watch with a tiger’s eye beaded bracelet on the opposite wrist for a bit of contrast.

5. The Micro Print Short Sleeve Shirt

When it comes to style, subtlety is often underrated. Where the floral or tropical print shirt demands attention, the micro print shirt fades into the background.


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It’s not nearly as loud as a bold print shirt and therein lies its subtle charm. That’s not to say subtle means flat or boring either. A repeating micro pattern is still quite visually interesting and can command attention.

There’s also something pleasing to the eye when we see repeating, symmetrical imagery.

How to Wear A Micro Print Short Sleeve Shirt

In this stylish outfit, I decided to rock a white short sleeve button down shirt that features a blue floral micro print (from Ash & Erie). I kept the white slim fit jeans from the previous look and swapped out the canvas Vans for a pair of navy casual style loafers from Glyph

They have a loafer’s silhouette and is made of a stretchy material that’s actually digitally knit from recycled fibers. Talk about next level tech in menswear. The shoes even have a comfortable removable insole. 

Micro Dot Pattern Short Sleeve Button Down Shirt
WHAT I’M WEARING — Micro Print Shirt: Ash & Erie (15% off w/code Welcome15) | White Slim Jeans: Express (similar: Levi’s) | Shoes: Glyph (Save $20 w/code Glyph20)  | Watch: Seiko | Sunglasses: Van Vliet

And finally for the accessories, I again went with round frame sunglasses made with natural horn instead of the popular acetate variety. And on my wrist I opted for the classic Seiko 5 with a custom brown leather band. I also added a leather bracelet which is a great way to add some flair to otherwise simple summer looks.


And that concludes this article on how to wear a short sleeve button up shirt 6 different ways. I hope you are now equipped with styling inspiration to rock the short sleeve button down confidently! 

Cheers to your style,

How to Wear A Short Sleeve Button Down Shirt (Styled 5 Ways) | GENTLEMAN WITHIN


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