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- The great thing about boyfriend jeans? They can be rolled down for maximum warmth or rolled up for a little bit of breeze. They're especially cute with a tucked-in blouse and a classic ballet flat, two spring staples. $98.95 at
- Bonobos pants should be a spring wardrobe go-to for all Chicago men working through hard-to-predict temps. They feel appropriate for cooler weather but come in fun spring colors. After all, real men wear pink. $88 at
- Whether or not you dated a quarterback in high school, a varsity jacket is an adorably retro throwback to high school days. $70 at
- Add a leather jacket and moto boots for cooler days, pair with a nude wedge for warm weather. Either way you'll be perfectly on-trend in black and white. $548 at
- The fashion sneaker is huge this season and with good reason. It'll update any outfit, from a simple jeans-and-tunic combo to a minidress. $44.90 at Akira
- You absolutely can not go wrong with a leather jacket, and this All Saints version is as cool as they come $768 at All Saints
- The most essential accessory for this weather? A fun umbrella to brighten up dreary days. This Marc Jacobs find fits the bill. $58 at