It’s Almost Jacket Season, and I’m Betting This Will Be the Style I Wear Most

Shop With WWW is back with 48 hours of exclusive deals from our favorite fashion and beauty brands thanks to our buy now, pay over time friends at Affirm. Set your alarms for 12:01 a.m. PT on August 26, and in the meantime, make like our editors and prepare your wish lists. Here’s a taste of what we’ll be shopping during the event.

Ready or not, fall is almost here, which means it’s time to level up my layering game. Ideally, I’ll find one go-to outerwear piece that I can constantly reach for, knowing it will be the perfect addition to just about any outfit. Who What Wear market editor Indya Brown has already found her trusty topper for the season, and I’m quickly being convinced to follow her lead. The style she’s betting big on is a cropped jacket, and she’s getting ahead of the game by serving up A+ looks in this dreamy leather option from Theory. Oh, and I should probably mention that during our Shop With WWW event beginning August 26, you’ll get $100 off for every $500 you spend at Theory. Amazing, right?

As someone who lived in NYC for years, Brown knows a thing or two about dressing for colder weather. “I don’t like to immediately jump to heavy coats and jackets. We have all winter for that!” she says. “Instead, I gravitate toward pieces that aren’t bulky or too thick, like this cropped jacket. The cropped silhouette allows for so many outfit combos, so you really can’t go wrong with it.”

With Affirm, get it for 4 interest-free payments of $249*

This lightweight leather style is the perfect transitional piece to wear with current warm-weather favorites (like a knit dress à la Brown), but it can also be layered under a heavier coat in the winter. “I love the cut and shade of dark brown,” she tells me. “I think this would also look amazing with high-waisted flare pants and a tube top, or a classic turtleneck and pencil skirt come fall.”

With Affirm, get it for 4 interest-free payments of $149*. They had me at cashmere. This slightly longer style is ultra cozy.

With Affirm, get it for 4 interest-free payments of $149*. This topper is giving me London vibes. Just add loafers.

With Affirm, get it for 4 interest-free payments of $149*. The shacket trend is here to stay. Wear this one unbuttoned over a t-shirt or lightweight sweater.

With Affirm, get it for 4 interest-free payments of $249*. Your classic leather moto jacket’s polished older sister.

With Affirm, get it for 4 interest-free payments of $87*. Size up in this classic blazer for a more modern, cool fit.

With Affirm, get it for 4 interest-free payments of $159*. The best thing about a roomy trench coat is layering your favorite cropped jacket underneath.

*Your rate will be 0% APR or 10% to 30% APR based on credit and is subject to an eligibility check. For example, a $700 purchase might cost $63.25 per month over 12 months at 15% APR. Payment options through Affirm are provided by these lending partners: affirm.com/lenders. Options depend on your purchase amount, and down payment may be required. CA residents: Loans by Affirm Loan Services, LLC are made or arranged pursuant to a California Finance Lender license.