Short answer
Choose cloth for the places and seasons where you expect to wear these blazers & sport jackets. Ask the tailor about fibre, weight, weave and care for the specific options; a city's name alone does not determine the right cloth.
Textured weaves earn their keep — herringbone, flannel, hopsack — with patch pockets and half-lining for movement and packability.
May suits lighter weights; September plans deeper cloths for the coastal winter.
The full cloth books span fresh open weaves through four-season high-twist to winter flannels and cashmere blends. Bring the tailor your calendar; the shortlist comes back two or three cloths wide.
The itinerary is a proposal: months are planned, dates and venues confirmed individually. Final quotations are confirmed in writing before you commit.