Simons’ B London tweed jacket lands in that sweet spot between professorial gravitas and downtown nonchalance. The chocolate fleck reads rich under daylight, and the semi-slim (London) cut sits neatly over knitwear without bulking the chest. Notched lapels, patch pockets, and a forgiving shoulder make this an easy week-to-weekend layer; the tweed’s subtle slub gives texture to plain tees and oxfords alike. Pair with indigo denim and a caramel crewneck for tone-on-tone warmth that still feels modern. A quietly luxurious Canadian staple. Price (CAD): $395.00