Chicago's Haberdash has a knack for inspiring men in the Midwest to step up their style without taking them too far out of their comfort zone. They've accomplished this by carrying brands that produce updated, relevant versions of simple menswear staples like jeans, woven shirts and jackets. Speaking of jackets, Italian brand L.B.M. 1911, a casual offshoot of Italian manufacturer Lubiam, is noted for its easy-wearing, unstructured blazers that often incorporate fabrics that have been specially washed. Made from a variety of fabrics like moleskin, wool and cashmere, Brad at Well-Spent recently pointed out they can currently be had at 1/3 of the price off. Our pick? The olive plaid jacket is both versatile and uncommon. At $400, it's still a tad pricey, but it's a piece we can see being worn again and again.
L.B.M. 1911 Olive Plaid Jacket, $400 at Haberdash
(Call 312.624.8551 to purchase)