I'm thinking something nostalgic rather than modern, simple rather than fancy... a bespoke tailor is a rare thing. ...a logo should make you long for the days of yesteryear when there were not 5000 suit a day factories.
That's why mine is perfect, and I deserve a (4000) new bespoke suit(s). Kidding ... but I do agree that a logo, regardless of the company, should remain timeless. Look at Jil Sander.. JS has been using the same JIL SANDER (I think it's Futura Extra-Bold
) logo since the 70s when Peter Schmidt designed it. Jil Sander is surely not a Savile Row tailor, but has consistently remained loyal to her specific artform and style, and that should be reflected in the logo.