Now and Later: What to wear into fall

From flip flops and winter coats to rain boots and t-shirts, it’s clear that dressing for the awkward transition between summer and fall is a struggle for many. Personally, my head is running in circles attempting to solve the great debate of jacket vs. sweater. Speaking of debates, how long can I get away with wearing a maxi dress? And when do I have to officially stop wearing sandals? These are just a few questions I ponder when that first chilly (and ugly) day arrives. If you’re in Chicago, that day has already happened and I’m sorry.
But enough debating, to save me (and you) the headache of transitional dressing, I put together easy looks to wear now and how to style the same item of clothing later–when it REALLY gets cold.
Sweater: The gray crew neck sweater is a classic. For temps closer to 70, pair it with tailored shorts and sturdy sandals. Slide into jeans, structured loafers, a coat and warm wool hat for later.



Sweater: H&M, $25

Now: Necklace: Icing // Shorts: Scotch & Soda //Sandals: Birkenstock

Later: Jeans: Uniqlo // Shoes: H&M // Hat: H&M // Jacket: Blackfive

Skirt: The flippy leather skirt is a great material for fall and winter. The wind blocker works well with a graphic t-shirt now and with tights later.


Skirt: Us Trendy,$44

Now: T-shirt: J.Crew // Earrings: ModCloth // Boots: Sam Edelman

Later: Jacket: Madewell // Sweater Tory Burch // Tights: H&M // Boots: C.Wonder

Ripped Jeans: A more relaxed approach to denim is making waves this season. A nude pump is perfect for warmer weather, but swap to boots when the weather turns.


Jeans: J.Crew, $100

Now:  T-shirt: Old Navy // Sunglasses: Nasty Gal // Necklace: Aha Life // Bag: Blackfive // Pumps: Sole Society

Later:  Sweatshirt: French Connection // Scarf: Alexander McQueen // Coat: J.Crew // Boots: Nine West

Sweater Dress: The sweater dress is my most reliable cold weather get up. Go bare legged now and add fleece lined tights for chilly fall and winter evenings. 

Sweater Dress

Dress: Uniqlo, $50

Now: Necklace: Baublebar // Bag: Paulina Carcach at Iristocracy // Pumps: H&M

Later: Jacket: Chicnova // Lipstick: NARS in Geraldine // Scarf: Need Supply // Boots: Paolo

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