Black suit + Black tennis shoes + Silk Handkerchief

His favorite part of this look is the plaid shirt, which he has taken the time to sew up any holes in over the years, just to keep wearing it.  Topped by a J Crew cardigan, baseball cap, and black rimmed glasses. 

                                               Photo by: Millie Jones

A bright color and a big bag will get you through the day.
Photo by: Millie Jones

Mix of plaids with a classic belted rain coat in neutral.
Photo by: Millie Jones