He took out a pile of shirts and began throwing them, one by one, before us, shirts of sheer linen and thick silk and fine flannel, which lost their folds as they fell and covered the table in many-colored disarray. While we admired he brought more and the soft rich heap mounted higher — shirts with stripes and scrolls and plaids in coral and apple-green and lavender and faint orange, and monograms of Indian blue. Suddenly, with a strained sound, Daisy bent her head into the shirts and began to cry stormily. “They’re such beautiful shirts,” she sobbed, her voice muffled in the thick folds. “It makes me sad because I’ve never seen such — such beautiful shirts before.”

The Great Gatsby by F. Scott Fitzgerald

I have never read words more powerful and more influential. Ever since I read the Great Gatsby and that shirt scene, I have become some what of a shirt connoisseur. A life time of experimentation has made me very discerning about the shirts I buy and wear. And all that experimentation has made me realize that shirts are the easiest and the most difficult thing to buy.

I don’t necessarily buy a lot of shirts. I just buy ones that feel great when I wear them. In other words, when it comes to shirts, I hate being trendy and instead focus on getting shirts that fit well, are very comfortable and are well made to last a few years.

I also avoid big brands such as Banana Republic. Instead, I seek out smaller lesser known brands who eschew trendiness and instead focus on high-quality fabrics, cuts, stitching and the general fit of the shirt. Of course, the other upside of a smaller brand is that you are less likely to run into another person wearing the same shirt.  

Being a man of girth, I don’t have much choice but to get shirts fitted so they are easy to wear and yet look great. In San Francisco, for instance, Cafe Coton (a french brand) offers well made and high-quality cotton shirts. I would recommend them over other brands such as Thomas Pink. While not cheap, they are well priced to accommodate $20-to-$30 per shirt in alteration costs. I think spending money on shirt alteration is an acceptable expense – because there is nothing worse than an ill-fitting shirt. Too loose and it seems you are floating in the shirt. If too tight, well too tight, specially if you have bulges in all the wrong place.

My test of a good fit is to wear a shirt and sit down as if you were at work on a computer. If the shirt gets stretched across your belly, you know it is too tight. Another test is — try and sit down and pretend you are sitting in the back seat of a car. If the shirt feels stretched, then it is too tight. Alternatively, make sure that the fabric doesn’t extend more than the size of one’s fist. Oh, make sure you make sure that when unbuttoned sleeves cover half your thumb. And one more thing about fit: at no point should the shirt sag at the shoulders.

If you are one of those fortunate people who are on the “lighter” side, I would recommend Emily Lafaurie shirts, which you can buy at the Sean stores in New York, Los Angeles, and San Francisco. There shirts have a more European cut — not a surprise since like Cafe Coton, they are a French company. The fabrics and the colors they offer are simply awesome. Given how my body structure, I don’t fit into their shirts, and that remains a regret.

Another brand I have recently discovered is Jeremy Argyle of NYC, which makes some great looking shirts. I have a couple of their shirts that have gone through the wash cycle and they haven’t lost their luster or shape. I have not gotten them altered as they fit well and while the sleeve is a tad long, I roll up the sleeves. They have become my favorite weekend shirt. (Read the Jeremy Argyle NYC)

One chain-brand company that makes great shirts is JCrew, though I have divorced them because they have started going in the tailored/slim fit direction. If I need to alter a shirt, I might as well step up a level or two. I still buy JCrew plain white dress shirts as they make them in traditional fit and they are exceptionally well made and are a bargain for the price.

Unlike Mr. Gatsby, I don’t think we can afford to have that many shirts. Damn, where is closet space. So I work on a simple principle: the total number of shirts in my wardrobe shouldn’t exceed 18. I divide the shirt quota into three categories — dress shirts, casual shirts and nighttime shirts. The final mix of the kind of shirts in your wardrobe depends on your lifestyle and your work. In addition, how you wear shirts also determines your shirt choices. I for instance, wear my shirts untucked so I can’t have shirts that are too long and too lose. However, the shorter shirts are also difficult for me

For instance, since my work doesn’t involve a very formal work environment, I end up wearing a pair of dark denim jeans pretty much every day. I pair them with shirts that fall between dress shirt and casual shirts. I love checks, so I have half a dozen of those shirts. I have an equal number of dress shirts – 4 white shirts and 2 blue shirts. Rest of my shirt quota is devoted to big, bold shirts that you see me wear at many of the GigaOM events.

Hope this is helpful. Good luck re-making your shirt wardrobe.

This is the second part of my what a man needs series. My first post in the series was about Chukka Boots.