What to wear when it’s 50 degrees and drizzling in Chicago! Trench: I’ve owned this London Fog trench for so many years and they still make it! It’s truly an incredible staple and comes with a removable liner for extra warmth! I’m not sure about sizing with the current one as mine is so old so I’d just go off reviews! Also linking a beautiful Mango version at a lower price point! Jeans: new Madewell jeans, they’re amazing. Comfy, some stretch, TTS. Wearing 26. 5’6 for height reference. Come in tall and petite too! Sweater: Sezane, runs big! I’d size down but I got my regular size (S) and still love it! Its almost sold out in white but I’ll link a similar Sezane sweater. Keep in mind they’re natural mohair/wool blend so if you are super sensitive to itch, these aren’t the sweaters for you, but they don’t bother me! Sneakers: also owned for years, great even in rain as they’re a thick leather that wipe right off. Medium support—I’ve worn them all over Europe! Scarf: old Sezane, will link similar!