I love the look of a 3 piece suit but rarely have an opportunity to wear one. I think something like this is a good compromise. The tweed vest, flannel (hopsack?) blazer and moleskin pants all have a good depth of color and texture, and reference the formality of a 3 piece, without actually being super formal. The olive color of the tie and the slight accent on the pocket square bring it together colorwise.
Stanley Blacker for Homicks Navy Blazer - $4
Tweed Waistcoat - Free
Oleg Cassini Gingham Button-Down - $2.50
“The Taylor Tie” by Wilson’s of Greenfield MA - $3
Blue/Olive Accents Pocket Square - $1.50
Banana Republic Moleskin Trousers - $11
Bostonian Crown Windsor Shell Cordovan Wingtips - $7