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Going from t shirt/jeans to navy blazer/grey flannels can feel a big jump for us working in millennial spaces but the looks Simon spotlights here are a good starting point in that process

Year: 1960s

The Madewell Ruffled One Shoulder Midi Dress is just that dress

Finished with a concealed zip closure to the back, this designer dress is the perfect plus one to your next event

How to Stretch Leather Shoes Without Damaging Them 2026-07-26 Leather has a way of holding its ground before it softens

High-waisted Spencer jackets also didn't restrict the belly in any way, and longer coats could be worn cinched below the bust or simply hanging free, as you'll see next