Quality doesn't always coincide with the price tag — the fabric, interlining, buttons, construction, and cut matter most.
"Fine raw materials impact the overall feel of the shirt and proper construction ensures the shirt's durability and wear overtime," says Joe Hemrajani, master tailor of MyTailor by Hemrajani Brothers. "A suitable cut and fitting ensures a perfect silhouette for each body type."
Keep two words in mind when looking for materials — elegant and timeless. This applies to simply textures, small details, and patterns that add a touch of interest.
"A small or medium check pattern make great business to casual transition shirts," Hemrajani says. "Shirts with button-down collars are also considered business casual, as the buttons help keep the collar neat and straight without a tie."
It's best to avoid loud or intense colors for daytime business wear.
"Whites and Blues are any field standard," he adds. "Lavenders and pinks can add some character, while greens, reds, yellows, and other colors add some variety."
Dress shirts remain the transitional anchor of every man's look.
"You can never be over-dressed. The best outfit is a suit," says Hemrajani. "Dress shirt, trouser, and jacket combinations allow more interest and versatility, while jeans will make for a smart casual look."