Ashley Olsen's 6 Most Magnificent Outfits of 2019, Ranked by Me

Following Ashley and Mary-Kate Olsen's personal style is a double-edged sword. On one end, the two typically avoid public appearances, so spotting a new outfit on either of them is rare. On the other, when it does happen, it's always inspiring. As 2019 comes to a close, I found myself reflecting on the best trends and outfits from the year and ended up on a quest to find out the best Olsen outfits from 2019. Today, I'm focusing on Ashley. Was there a ton to choose from? No, we covered that above; she's a unicorn. Were the available options insanely chic? Yes, yes they were.

Ahead, see the top six Ashley Olsen outfits from 2019, ranked by me, and shop my picks along the way to infuse your wardrobe with her signature laid-back polish.

#6: Square-Toe Endorsement

Ashley Olsen Square-Toe Heels


Hewitt /

Both Ashley and Mary-Kate have always led the charge when it comes to grandma dressing. It's no wonder now that square-toe shoes are making a comeback Ashley is full steam ahead. This year, she paired hers with a black blouse and trousers punctuated by an oversize embroidered scarf. Pure effortlessness.

#5: Old Faithful

Ashley Olsen Black Dress


ECP/GC Images

If there's one color Ashley knows how to wear, it's black. Red carpet, on the weekend, to dinner, any scenario—she's got a noir look for it. This CFDA moment was the most romantic of 2019.

Ashley Olsen Camel Coat


Jawad Elatab / BACKGRID

Ashley's always been one for a good coat, so this beautiful camel-suede number is no surprise. Also, if you're not into leather, there are plenty of faux options on the market that capture the same vibe.

#3: Pop of Python

Ashley Olsen Python Dress


Robert Kamau/GC Images

I tend to think of Ashley Olsen as an individual who eschews trends, which is why this python-print dress was slightly unexpected. That said, her riff on the pattern feels in sync with her personal style; long fur coat on top, sleek black accessories to finish.

#2: Relaxed Fit

Ashley Olsen Baggy Pants



Ashley has always favored comfort and ease in place of curve-skimming silhouettes. The result is an insouciant vibe that makes you want to reach for your baggiest trousers and seize the day with laid-back confidence.

Did you see? Our Fall Issue cover star is Elizabeth Olsen.