
Fit can be a tough topic to wrap one’s head around. Many don’t understand that a few small alterations will elevate their style game from bad to good — or from good to great. Oftentimes the first step to looking better is admitting that some clothes, however sentimental, don’t quite fit right.
The other half of the battle is finding a good tailor. Kirk Miller, co-founder of Miller’s Oath in New York City, is a Minnesota native who developed a love of tailoring from a young age, finding inspiration through his father’s bespoke Anderson & Sheppard suits. After beginning as a bespoke tailoring business nearly nine years ago, Miller’s Oath has since expanded into ready-to-wear formal and casual wear. So if you’ve come to find that tucking in your shirt so that it looks right is an unreasonably delicate operation, listen up.
Buy a shirt that doesn’t need tailoring. Many men buy button-front shirts that don’t quite fit; they either buy into the slim-is-always-better ethos, wearing shirts that threaten to burst at the seams, or, more commonly, opt for shirts with a billowing body, slouching shoulders and sleeves that droop past the wrist. The common-sense solution for the latter is sending these ill-fitting shirts to the tailor, but Miller thinks you’re better off skipping the alterations altogether. “If your shirt doesn’t really fit well,” he says, “I would argue go find a shirt that fits rather than alter a shirt that doesn’t fit.” Miller recommends a shirt with a tapered — but not tight — body and cuffs that hit the wrist. This gives the shirt a proportional look that’s neither skinny nor baggy.
Shorten the jacket sleeves. Though Miller isn’t keen on shortening shirt sleeves, he says sleeve alteration is imperative on a blazer or suit jacket. You don’t need them cut as high as Sammy Davis Jr.’s suits, but they should show a little cuff. “It should be on your wrist, not on your thumb,” Miller says. “Some guys are still scared by that.”

Miller also advised that coats — even in fabrics like tweed and corduroy, which are associated with roomier fits — look best when the sides are tapered. When dressed down, it makes blazers easier to pair with casual garments. “I always think a little bit of shape on a sport coat is really nice, especially when you’re wearing it with a pair of jeans,” he says.