Pass up the typical briefcase for a stylish backpack like this one from 3.1 Phillip Lim. Dual zippers and tons of space inside mean plenty of room for your laptop, iPad, and other work items.
31 hour zip around backpack, 3.1 Phillip Lim ($1,100). Barneys New York, 15 E. Oak St., 312-587-1700
Chicago-based line Two Penny Blue is a go-to for great blazers, and as the line’s signature product, they’re available in every color of the rainbow. Go bold for the new season with a blazer in emerald, fuchsia, or mint.
Be top of the class in a limited-edition frame that gives a modern update to a classic style. In fact, the relaunched unisex frame is the same one the designer himself wears. The spotted tortoise/olive shade is especially academic.
PS-294, Paul Smith ($380). Oliver Peoples, 941 N. Rush St., 312-266-9000
After a long day sitting at a desk, slacks and jeans often loosen up. Not so with Madewell’s just-released denim, which uses a state-of-the-art fabric to keep the fit consistent all day long. And, thanks to a new store in the Gold Coast, they’re now available in Chicago.
Skinny skinny high riser jeans, Madewell ($125). 932 N. Rush St., 312-337-3815
Chicago menswear staple Haberdash recently debuted its e-commerce site, and the Austen Heller brand launched in 2012. The two new entities make the grade with these Ivy League loafers.
Suede driving Moc loafer, Austen Heller ($195). Haberdash, 607 N. State St., 312-624-8551