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3 Fall Outfits for a Long Shorts Season

Written by:Sarah CarrPublished on:
Fashion editor:Sarah Carr

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Photo courtesy of Sandra Semburg

Deciding when to phase shorts out of the outfitting agenda is a classic September issue, but with the weather and the Bermuda short still hotter than ever, we’re officially granting our summer favorites an extension. Coincidentally, the polished silhouettes we’ve been wearing all season fold flawlessly into the fall lineup, for a smooth sartorial transition that won’t make you break a sweat. Here, three looks to make shorts season last a little longer.

Sneak Your Shorts into the Office

Depending on your office’s outfitting politics, sneaking a pair of polished Bermudas into the building makes saying goodbye to summer Fridays less sad, more chic. Done in office-appropriate khaki, this pair is decked out with trouser-adjacent details, but the silhouette is streamlined, so it plays nicely with the rest of your work wardrobe. Pair it with smart aviators and the bag you bribed yourself back to work with for a look that elevates your executive functioning.  

  1. Glasses
    CartierGlassesNet-a-Porter, $1,195shop now
  2. The Boyfriend V-Neck Sweater
  1. Duchess Satin Tee
    TotemeDuchess Satin Teegoop, $336shop now
  2. Belt
    LoeweBeltLoewe, $690shop now
  3. Morgan Short
    GWYNMorgan Shortgoop, $525shop now
  1. Tote
    TotemeTotegoop, $1,290shop now
  2. Kitten Heel
    Le Monde BerylKitten Heelgoop, $565shop now

Ease into Sweater Season

When you’re ready for a chunky knit but the weather won’t cooperate, the long-short-plus-light-sweater setup satisfies the craving. Zipped down to a deep-V to show off your necklace stack, this preppy polo pushes your color palette toward fall without going full leaf-peeper, and it creates a cool contrast with the dusty-rose cargo shorts. 

  1. Necklace
    Marlo LazNecklacegoop, $4,400shop now
  2. Bag
    The RowBagThe Row, $1,090shop now
  1. Augusta Sweater
    GWYNAugusta Sweatergoop, $565shop now
  2. Remy Short
    GWYNRemy Shortgoop, $495shop now
  1. Sunglasses
    Brunello CucinelliSunglassesMyTheresa, $720shop now
  2. Sandals
    AeydeSandalsNet-a-Porter, $625shop now

Take Your Shorts Out on the Town

Like a red velvet suit at the VMAs, a pair of shorts dressed up after dark is sexy in the coolest way. The Arden Short makes it easy: The high A-line hem has a feminine flip, so it’s perfect for pairing with other unexpected night-out silhouettes. Lean into the menswear moment with a silk button-down so sheer, it practically floats, then add a fringed leather bag and slip on a pair of wedges—a practical pick for the dance floor.

  1. Daphne Bra
    GWYNDaphne Bragoop, $150shop now
  2. Pumps
    TotemePumpsNet-a-Porter, $700shop now
  1. Stella Shirt
    GWYNStella Shirtgoop, $595shop now
  2. Arden Short
    GWYNArden Shortgoop, $450shop now
  1. Ring
    Lucy Delius JewelleryRinggoop, $9,630shop now
  2. Bag
    Fuentes MierBaggoop, $1,325shop now

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