This Jacket Trend Makes Every Outfit Look Expensive—25 Picks I'm Obsessed With

Contrary to popular belief, the best time to buy a jacket isn't winter. It's the weeks right before fall. Transitional-weather dressing is my personal Achilles heel. Fall's seasonal volatility means I'm walking out of the house in a cute outfit that leaves me feeling cold more often than not. The 50- and 60-degree weather is hard to dress for, but thankfully, I'm finding sartorial joy thanks to the one simple, elevated jacket silhouette that makes me feel like old money: collarless jackets.
Fall's sleeper jacket trend has to be one of my favorites of late due to its endless possibilities. Quilted jackets, tweed blazers, and worn-in leather jackets go with anything. For more traditional styles, the preppy East Coast Americana look fits right in with the quiet-luxury movement happening as of late. If a single collarless jacket takes my outfit from simple to Shiv Roy, I'm here for it.
Below, browse a few of my favorite collarless jackets, including a few ways to style them.
What you need: leather collarless jacket + maxi skirt + neutral bodysuit
What you need: structured collarless jacket + straight-leg denim
What you need: quilted collarless jacket + statement pants + white T-shirt
What you need: tweed or wool collarless jacket + dark-wash denim
What you need: collarless jacket or blazer + boxy trousers

Ana Escalante is an award-winning journalist and Gen Z editor known for her sharp takes on fashion and culture. She’s covered everything from Copenhagen Fashion Week to Roe v. Wade protests as the Editorial Assistant at Glamour after earning her journalism degree at the University of Florida in 2021. At Who What Wear, Ana mixes wit with unapologetic commentary in long-form fashion and beauty content, creating pieces that resonate with a digital-first generation. If it’s smart, snarky, and unexpected, chances are her name’s on it.
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