Learning how a shirt should fit you can take surprisingly long – as most fans of bespoke try far fewer shirtmakers than they do tailors. Once learned, however, the lessons are fairly simple. They are becoming particularly clear to me as I complete my shift from Turnbull & Asser to Satriano Cinque. (Updates coming soon on the latest shirt commissions from them.)
The biggest lesson is not to obsess about how a shirt fits on the waist. To a young man trying to look as sleek and athletic as possible, a closely fitted shirt is an understandable focus. Italians heavily dart their shirts to this purpose; in the past I have darted and redarted my own darts in pursuit of that same, perfect fit.
2. Focus on the collar
Ideally, the shape should work with and without a tie (so not collapsing underneath the jacket’s collar). If that’s not possible with your jackets and neck shape, have just two collar types: one for a tie (perhaps a medium spread) and the other for an open neck (probably a buttondown).
3. Consistent sleeves