5 Fall Outfit Combos From the Chicest 50-Somethings in Hollywood
At long last, fall has arrived. After months of anticipating the season's hottest colors, shoes, and jewelry, it's finally time to translate all our fall trend predictions into full-blown outfits now that the temps are steadily dropping. And who better to inspire our autumnal ensembles than the chicest 50-somethings in Hollywood?
With Julianne Moore stepping out in an of-the-moment outfit complete with this season's most talked-about shoes and Cindy Crawford making a compelling case for the classic skinny jeans and ankle boots outfit formula, we've already spotted some major inspiration. Of course, Halle Berry, Nicole Kidman, and Demi Moore are offering up some serious style inspo as well.
Keep scrolling to see how these stylish 50-something celebs transition their wardrobes for fall, and shop their looks for your own closet if you're so inclined.
While a number of stylish celebs can't stop wearing knee-high ankle boots, leave it to Cindy Crawford to make a compelling case for pairing classic pointed-toe ankle boots with skinny jeans and a leather jacket.
Allow Julianne Moore to demonstrate how to craft an outfit around all of the season's most talked-about trends. Pleats? Check. Tall slouchy boots? Check. Top-handle bag? Check.
For a laidback look, layer an oversize sweater over anti-skinny jeans, as Halle Berry does here. Take style notes from the star and roll the hems to show off a pair of ankle boots.
Take a page from Nicole Kidman's book and balance out a pair of edgy combat boots with an oversize blazer and skinny jeans for a polished fall outfit. Naturally, a knit sweater completes the look.
Go bold like Demi Moore did by pairing a bright, chunky knit sweater with a pair of wide-leg plaid trousers. Complete the look with a simple overcoat to account for fickle fall weather.
Up next, six ways to wear fall boots like Cindy Crawford, Nicole Kidman, and more.
-
If I Saw You in Any of These 15 Summer-to-Fall Transitional Outfits, I'd Think You Hired a Stylist
Nice taste.
-
Put Down the Black and White Pants—This Is the Richer Color You Didn't Know You Needed
Elegant and on-trend.
-
What You Should and Should Not Wear to Every Major Sporting Event
From a Liberty game to the French Open.
-
10 Outfits Europe's Chicest Dressers Are Wearing When They're *Not* on Vacation
Staying local is cool.
-
Just to Be Clear, *These* Are the Pants Fashion People in L.A. Are Wearing Instead of Basic Jeans
Spotted in Paris too.
-
The Coolest Outfits of Summer 2025 Are Actually the Laziest—Let Me Explain
Easy does it.
-
I Just Created 5 Incredibly Chic Summer Outfits From Amazon for Under $190
Cool looks for less.
-
Don't Pack Up Your Sweaters Just Yet—Cool Fashion People Are Repurposing Them in the Chicest Way for Summer
All the outfit inspiration is inside.