3 Fall Outfits We're Wearing for Every Occasion

These days, we find ourselves expecting more from our fashion purchases. While we can't say we've never bought an over-the-top special-occasion dress and only worn it once (of course we have—we all have), we generally aim to invest in pieces we'll wear many times and in many ways—think coffee-to-cocktails situations. And in the name of said versatility, lately we've been turning to transitional pieces from Ann Taylor's new Luxewear line. The collection features all of the double-duty essentials we need to create fail-proof outfit ideas all season long (and for many seasons to follow).

Ahead, see the three that are sure to save us many hours of staring blankly at our closets.

Tailored Trousers + a Cozy Sweater


The first fall dressing rule we'll be implementing? The whole "do more with less" concept. To wit, we're leaning toward wearable pieces with interesting details that only create the illusion of long hours spent getting dressed. Enter: this simple trouser-and-sweater combo. The on-trend check pattern gives the pants a polished feel, while the equestrian-style stirrups add just the right amount of playfulness. Top it off with a cozy knit featuring a punchy hue and oversize wrist ties, and you're set with a two-piece uniform you can wear all over town.

Layered Knits


Next up is a multilayered look for those extra-chilly days. Piling on extra pieces doesn't have to be complicated, though. It's all about playing with the length and fabrication of versatile staples so our outfits come out sleek, not sloppy. The key elements that make this one so successful? A simple blouse, a sleeveless chunky knit, and a soft cardigan that falls just above the knees. The addition of heeled suede booties means we won't even have to change our shoes when inevitable last-minute dinner plans come up.

Menswear-Inspired Separates


Our final fall outfit solution involves a piece that has yet to fail us in this lifetime: a menswear-inspired blazer. As far as we're concerned, any outfit that involves a borrowed-from-the-boys aesthetic is a winner, perfectly balancing sophistication and trendiness. While we love wearing our trusty blazer with everything from denim to dresses, pairing it with cropped pants and a matching knit top is a really cool way to create a look that's just a bit more luxe. We're just as likely to wear this outfit to a Monday morning meeting as we are to Sunday morning brunch (especially with crisp white sneakers).

Feeling fall outfit fatigue a bit prematurely? Shop the rest of Ann Taylor's Luxewear collection for stylish pieces that look chic whether you're on-the-go or off-duty.

Associate Fashion Director, Branded Content

Michaela Bushkin is the associate fashion director on the branded content team. She is based in Los Angeles and is going on her sixth year at Who What Wear. Michaela has always worked in the content world, previously at Whalerock and The Zoe Report. Her current role involves executing content, photo shoots, and events for fashion brands from retailers to luxury designers and everything in between. She spends her free time online shopping (or "researching" as she likes to call it), reading at the beach, and trying as many new restaurants in L.A. as possible.