In Search of the Perfect Dress Shirt

Dress shirts are not as simple as they seem. Yes, they’re plentiful and often cheap, but finding the “perfect” dress shirt (i.e. one you truly love) is a challenge.

You can’t just buy a generic “fitted” dress shirt and expect it to look great.

It can take years to whittle down the details and discover your favorite maker, fit, fabric and size.

Because it’s all in the details.

The fabric, collar, cuffs, pattern and most of all – the fit – are elements that come together for dress shirt perfection.

Some basic tips:

  • Choose fabric that feels, moves, and breathes naturally. Don’t buy non-iron shirts.
  • Decide what collar looks best on you, whether it’s a sporty button down or rakish cutaway spread.
  • Determine your actual neck and sleeve size; then decide if you want a classic or slim fit. Consider adding darts if you would like an even slimmer fit.
  • Experiment with different brands. You’ll be amazed how different they are, even when the basic design of the shirt appears to be identical.

When to Buy Custom

If you’re an odd size, just get made-to-measure shirts. Years ago, I wrestled with poor fitting shirts, and then decided to go made-to-measure and stop wasting money.

I’ve tried many different tailors and learned that I need to pay a little bit more to be satisfied. Choose an awesome tailor and great fabric. You’ll get shirts you love, and they’ll last for years.

I like my custom shirts so much, I bring them in for repair when they begin to wear out.

Recommended Shirt Brands

Brooks Brothers
My personal favorite, because I love the button down collar, and nobody does that better than Brooks.

Proper Cloth
A fun online shopping experience, fast delivery for custom shirts, and decent quality

Kamakura
Japanese craftsmanship, inspired by British and American style

Gitman Bros Vintage
Classic made in USA quality oxford shirts

Borrelli
Classic handmade Italian dress shirts

Eton of Sweden
Stylish eye-catching fabrics and rakish spread collars

Turnbull & Asser
Classic made in England quality