Somewhere in the bible, I’ve heard it’s said, “Eat good food, drink good wine, anoint your head with the finest oils, wear fine clothing, and love the wife of your youth.” Aside from ‘love the wife of your youth’…’wear fine clothing stands out to me.’ After all, nine out of ten people in biblical times lived close to or below the poverty level, and therefore didn’t have much clothing, let alone fine clothing. 

However, if there’s one article of clothing that is most useful, and probably the first ever from Stone Age times to now, it would be the shirt. And just like there are different quality wines, there are different quality shirts. Here’s a quick history on the dress shirt:

Made from linen or cotton, the dress shirt originated in the 17th century as an undergarment for wealthy European men to absorb sweat and protect their outer clothing. Around 1871, buttons and the precursors to modern collars were introduced into the design. During the 19th century, factory-made shirts became available that were fastened at the neck and wrist with buttons. By the 20th century, shirts became more casual, and were worn by the general public. 

As someone who has sewn clothes for over fifty years (including men’s dress shirts) today’s column is dedicated to the elements that constitute a fine quality man’s shirt; a garment that also looks chic on a woman, especially when accented with a scarf or cinched around the waist with a belt. Following are eighteen ‘must haves’ when evaluating a fine high quality dress shirt: 

1. Must be made of premium natural fibers such as cotton, linen or silk.

2. Must have a tailored fit.

3. Must have pleats on the back panel for ease of movement.

4. Must have a high quality collar that perfectly frames the tie.

5. Must have removable collar stays (the best are made of metal) for laundering and when in place to keep the pointed ends of the collar from curling.

6. Must have hand-sewn cuffs that can be unbuttoned to lie flat in order to easily pull the sleeve over the hand.

7. Must have a split yoke, which is the piece of fabric at the back of the shirt in the shoulder area.

8. Must have reinforced side seam gussets; those small pieces of triangular fabric sewn in where the side seams meet the hem of the ‘skirt.’ This prevents the shirt from ripping during tucking and untucking practices. It also adds a minimal flare to the overall design.

9. Must have Mother-of-Pearl buttons.

10. Buttons must be tightly sewn. 

11. Must have cleanly finished buttonholes. 

12. Must have fine stitching all around.

13. Must have flat-felted seams.

14. If a print must have pattern matching.

15. Must have single needle stitching all over. 

16. Must have a small button at the sleeve placket.

17. Must come with spare buttons.

18. Must have a finely rolled hem.

As you can see, it takes many fine, perfectly crafted details to make a high quality shirt, which is why you can expect to pay anywhere from $50-$200 or more for a new one. Hopefully this list helps you understand what to look for when seeking the ideal men’s shirt be it in an upscale clothing shop or secondhand store.

RAMONA JAN is the Founder and Director of Yarnslingers, a storytelling group that tells tales both fantastic and true. She is also the roving historian for Callicoon, NY and is often seen giving tours around town. You can email her at callicoonwalkingtours@gmail.com.