The Journal — Menswear

The question of what groomsmen wear is one of the most overthought decisions in wedding planning and one of the most underthought in execution. Many wedding parties end up in rented tuxedos that fit badly, or in matching navy suits bought off a rack in sizes that fit no one exactly. The result is a wedding party that looks like a group that got dressed together, rather than a group of well-dressed individuals with a shared aesthetic thread.

A new suit — particularly a full canvas suit — is not at its best on the first day you wear it. This is not a deficiency; it is how canvas construction works. The floating canvas inside the jacket needs time to conform to the specific geometry of the chest wearing it. The fabric needs time to relax and settle into the shape it will hold for years. The first month of wearing a new suit is an active process, not just an introduction.

The shoe is the first thing a tailor looks at when assessing whether a suit fits correctly — because the trouser hem, the trouser break, and the visual proportion of the leg all depend on the heel height and silhouette of the shoe. It is also the detail that most reliably finishes or undermines an otherwise well-considered suit outfit.

The suit-and-sneakers combination is one of the most discussed and most frequently failed looks in contemporary men's dressing. When it works, it reads as effortless and knowing — the person who is so comfortable in formal clothing that they can pair it with something unexpected without looking like they're trying. When it fails, it reads as a costume: either too deliberate or simply incongruous.