6 Staples I'm Buying Before Fall Starts for an Elegant Wardrobe

I'm obsessed with Carolyn Bessette-Kennedy's style, so as I started to think about how I'd like to dress for fall, she was the first person who came to mind. My relationship with her style has evolved over time, and as I look at her today, there's one word that my mind jumps to to describe all that she is: elegant. Without even trying, she gives off the stealth wealth vibes that simply scream effortless elegance. As fall approaches, it's the perfect time to draw inspiration from her paparazzi moments.

Whether you're stepping into a crisp autumn day to get a coffee or attending a formal evening event, you're going to want to look elegant. I decided to round up some staples that do just that. With Bessette-Kennedy in mind, channel timeless style with these picks.

1. Cool Vests

Woman wearing elegant fall staples.

(Image credit: @annelauremais)

Tailored vests are evolving from the traditional V-neck cut to high necklines and longline silhouettes. Whichever vest you choose, you can't go wrong this time of year.

2. Structured Jackets

Woman wearing elegant fall staples.

(Image credit: @mimixn)

The era of oversize jackets is over, and it seems like people are taking their favorite jackets to the tailor or buying them fitted. This has more of a '60s vibe to me, and I'm obsessed.

3. Column Skirts

Woman wearing elegant fall staples.

(Image credit: @alyssainthecity)

Right now, there's nothing more elegant to me than a column skirt. It's the floor-sweeping wardrobe staple that you can add any top to, and you'll look extremely elegant. If I could find a '90s Calvin Klein version of this, I'd go after it.

4. Watches

Woman wearing elegant fall staples

(Image credit: @tylynnnguyen)

Buying a timeless watch shows that you know how to make a smart purchase, and what's more elegant than that? I've been vying for the classic timepieces that have been in the hands of fashion-industry insiders for generations while also loving some of the new designs.

5. Trench Coats

Woman wearing elegant fall staples

(Image credit: @sylviemus_)

Oversize trench coats are winners in my eyes, and as soon as it's warm enough, I'll be sliding into them. They're perfect on top of, well, everything. I'm in the market for a black one right now.

6. Pointed Flats

Woman wearing elegant fall staples.

(Image credit: @nlmarilyn)

I just got my first pair of pointed flats and simply can't wait to wear them out and about. They're a chic memento and very easy to walk around in. Something about flats feels more luxurious to me than most heels.

Sierra Mayhew
Fashion Editor

Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of experience in the fashion industry to the editorial team. Since joining Who What Wear in 2021, Sierra has made her mark by expertly blending luxury and accessible fashion content. Whether she's decoding the latest runway presentations or crafting a perfectly curated shopping list, Sierra's keen eye and relatable approach have solidified her as a trusted voice in the fashion space. She's also reported on major industry events like Paris Fashion Week and lent her expertise to red carpet coverage, ensuring her audience gets an insider's view of the most glamorous moments in style. Before joining Who What Wear, Sierra sharpened her skills at Harper's Bazaar and Elle, with bylines in Bazaar.com and collaborated with iconic brands such as Gucci and Ferragamo. Her ability to translate editorial expertise into viral social media content sets her apart, seamlessly bringing her articles and personality to life for a new generation of readers and followers. A graduate of the University of Notre Dame, Sierra brings a unique perspective to the fashion industry that is informed by her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.