A few favorites I’m reaching for right now: breathable leggings by Swaby, paired with a crisp linen tee from Production Mode, and topped with the kind of lightweight jacket from Confidence Apparel that works for both early mornings and cooler nights. My husband recently picked up a casual jacket from Khamryn B Mens, which he’s been wearing nonstop with what he swears are the most comfortable jeans in Chicago—from Mugsy. Whether you’re keeping it low-key with clean sneakers or dressing it up with something more structured, these pieces carry you through the season without missing a beat.