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Once you get the shirt to fit, then you can address the specific details. The major considerations are fabric, colors. and patterns. 

Go with 100% cotton shirts.  Cotton is soft and resilient – everything you'll need in a shirt.

And while we're on the subject of fabric, make sure the fabric is opaque; no one wants to see your chest hair through your shirt, or worse, your nipples.  

Don't punk out and get all white and blue shirts.
  Mix in some stripes and other patterns (tattersall, gingham, etc.) with solid colors. Try colors that complement the suits and ties you have, but can stand alone during non-work hours, too. You'll need a dozen, so you have some room to experiment.  

Only wear shirts with colors found in nature.  Many guys didn't abide by this rule in the '80s. Electric blue, neon pink, gold lame'… bad, bad, bad.

Unless you're working mission control at Johnson Space Flight Center in Houston, never wear a short sleeve with a tie.

If you are wearing a tie with a shirt,
unless it's a buttoned-down collar or tab-collared shirt, it needs collar stays, those plastic things that look like small pointed Popsicle sticks. They keep your collar flat, and without them you get wings flapping beneath your chin. You can buy them at your dry cleaner.

The other critical details to consider are the collar and the cuff.

Collar

Believe it or not, there are several types of collars, with different uses. The shape of your face, what you plan to wear with the shirt, and the time of day you wear it will factor into the type of collar you can wear and will need. We've done the hard work for you and boiled it down to the essentials.

Pointed -- Most shirt collars you find will be pointed because it works for most faces, particularly wide or round faces.

Spread -- The span (the area where a tie goes between the collar points) is wider than all other collars, which means if you have a round face, spread collars only make your moon face look moonier. The spread is better for narrow faces.

Tab (tabs fasten at the top of the collar to hold the collar in place) --
 More formal style; works with any face, particularly for longer or oval faces.

Button down (collar points button to the shirt) -- A more casual look most commonly associated with Oxford shirts. It's better worn with a sport coat for a more relaxed look and feel.

Rounded (also known as Eton) -- Kind of foppish in a Victorian sort of way, the Eton works with a face that's long or square and in English boarding schools.

Cuffs

"The Half-And-Half Rule":  While we don't endorse mathematics when it comes to clothing (or ever), we do endorse the half-and-half rule. Approximately 1/2" of collar should show above your jacket collar and 1/2" of shirt cuff should show at the wrist. This compliments the shape, cut, and color of the suit and helps to frame your face.With cuffs, it's a little easier to navigate than collars.  You only have two options. Unless it's a dashiki or some sort of tunic, a shirtsleeve with out cuffs is a smock. Men do not wear smocks, at least not since 3rd-grade art class. While we're talking about cuffs, we suggest getting a shirt with gauntlet buttons (the gauntlet is the split of the sleeve from the wrist to the forearm). They make for a more polished appearance and are a sign of a better quality shirt.

Barrel cuffs -- They are the most common type found on shirts. Barrel cuffs button and we can bet that all of your shirts are barrel-cuffed shirts. They should fit comfortably around your wrist, meaning you can wear your watch without getting it caught on the cuff.

French cuffs -- They lend instant elegance to your look and give you another chance to show off your personal style. The cuff will fold onto itself and require cuff links or some other fastener, like silk knots. Be sure to line the buttonholes up when putting on the cuff links. Some men feel French cuffs are a little too dressyand opt for conventional barrel cuffs. French cuffs are a quick way to add style, so get over it and get some shirts with them.
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Guayabera
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Be Better Guys: Guayabera Men's Linen ShirtWant a better warm weather shirt? Get a guayabera. True guayaberas are made of linen, come in lots of colors, and have great detailing. They have a casual elegance, perfect for brunch, a date or a lounge. Available online through My Cuban Store and stores nationwide.
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