Transitional weather uniform: comfy, structured, and easy. This Free People pullover is the kind of piece that makes an outfit on its own — oversized but not sloppy, and the colors somehow work with everything. Paired it with these Madewell wide-leg crops (perfect ankle crop if you’re tall) and these Sam Edelman loafers that go with everything from jeans to dresses. Saved all the outfit details for you — it’s one of those looks that just works 😍 OutfitInspo OutfitIdeas StyleInspo StyleOver30 OOTD FallOutfitIdeas TransitionalStyle EverydayStyle CasualChic FallStyleInspo WhatIWore OutfitsOfTheDay TallStyle ElevatedCasual WorkToWeekendStyle LTKMidsize LTKTall LTKPlusSize

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Sam Edelman Loraine Bit Loafer in Soft Silver at Nordstrom Rack, Size 9 | Nordstrom Rack
We The Free Seaside Funnel Pullover | Free People (Global - UK&FR Excluded)
The Tall Perfect Vintage Wide-Leg Crop Jean | Madewell
Michaela Shine Mary Jane Flat (Women) | Nordstrom
Dolce Vita Alenia Perforated Mary Jane Flat (Women) | Nordstromrack | Nordstrom Rack
Tall Pull-On Barrel Pants in 100% Linen | Madewell | Madewell
Low Rise Long & Lean Jeans | Gap | Gap (US)
Men's Bean's Vintage Soft Rugby, Mockneck, Chest Stripe | Shirts at L.L.Bean | L.L. Bean
x We The Free Striped Travis Polo Tee | Revolve Clothing (Global)
ARRANGE compact stripe knit collar oversized sweater in ivory and forest green | ASOS | ASOS (Global)
Men's Long Sleeve Stripe Rugby Shirt | Lands' End (US)
Rising Sun Jersey in Storm | Revolve Clothing (Global)
Oversized Rugby Polo | Old Navy (US)
We The Free Aurora Zip-Up | Free People (Global - UK&FR Excluded)
Tall Low-Slung Baggy Jeans | Madewell
Tall Low-Slung Baggy Crop | Madewell
Tall Tapered-Leg Utility Pant | Madewell
Tall Pieced Barrel-Leg Jeans | Madewell
We The Free Atlas Dolman Tee | Free People (Global - UK&FR Excluded)