Permanent Style has a nice profile on Bruce Boyer, where the menswear writer talks about some of the things he’s been famously photographed in. It’s not only a fun read on a contemporary style icon, but it also has some useful tips on how to dress well (grey and tan make for good trouser colors, while brown and green work well for sport coats. Also, brown suede shoes can be worn with anything).
Incidentally, Boyer’s Eminently Suitable or Elegance are two of the best books on classic men’s clothing. Highly recommended reading, if you haven’t read them already.