I am in the medium of the tee — it is oversized! If you need a shorter look or just overall a smaller fit, go down one size. I am in the 10 of the trousers, perfect relaxed fit. The shoes run TTS.

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The Essential Medium Bucket Tote | Madewell | Madewell
Slouchy Straight Pants in Drapey Twill | Madewell | Madewell
Cashmere Oversized Sweater Tee | Madewell
Skinny Western Belt | Madewell