For those who might not know, former Dawson's Creek stars Katie Holmes and Joshua Jackson have reunited and are working on a new movie together: Happy Hours. Over the past few weeks, paparazzi have been out and about in New York City, capturing all the sweet moments between the two and keeping us fashion people updated on Holmes's chic directing and acting looks.
One of Holmes's outfits that caught our attention included a striped button-down shirt, culottes, and loafers. While it was interesting to see the cropped-pant trend gaining momentum after Hailey Bieber wore the style in May, what's also notable is the fact that Holmes chose brown leather loafers instead of open-toe flats like flip-flops, especially in the 90-degree weather.
If we think more about it, Holmes's shoe choice makes sense. Flip-flops are often seen as controversial in NYC, and leather loafers, especially in dark brown, lend a sophisticated and elegant appeal that can make any outfit—even a pair of culottes—look elevated. Plus, these shoes can be worn from summer to fall with everything from wide-leg trousers and baggy jeans to knit dresses and lace-trim slip skirts. Inspired to add a pair to your wardrobe? Keep scrolling to re-create Holmes's look and shop more rich-looking loafers.
Get the Look
Style this top with shorts and sandals in the summer and wide-leg trousers and loafers in the fall.
This will become the hardest-working piece in your wardrobe.
Bieber, Holmes, and Charli XCX are all on board with the culotte-pant trend.
Grab these before they're no longer on sale.
Shop More Chic Loafers
These don't come in brown leather, but they look a lot like Holmes's flats.
It doesn't get more classic than the Whitney Weejuns Loafers.
The Who What Wear fashion team is eyeing these for fall.
Ruched loafers, often called gathered loafers, bring added dimension and sophistication to the classic silhouette.
Sleek and chic.
According to our editor who owns these, they're extremely versatile and comfortable.
-
Navy This, Brown That—Sorry, But 99% of the Time, Fashion People Only Wear Leggings in *This* Classic ColorJust ask the L.A. Pilates crowd.
-
Not Slippers, Not Boots—These New Uggs Are Already Replacing Every L.A. It Girl's Favorite SneakersThey're $150 and they're yours.
-
The Shoe Color Trend That Makes Wearing Jeans With Blazers Look 2025 Instead of DatedAs seen on Jennifer Lopez.
-
People Always Compliment My Winter Outfits for Being Polished—These 7 Chic Items Are My SecretSimple pieces, big impact.
-
I Walk Over 5 Miles a Day Working in Manhattan—Here's an Editor-Approved City Girl's Guide to Fall ShoesPlus, how I'd style them.
-
J.Law Channeled Carolyn Bessette Kennedy in the Winter Hero Item That Makes Basic Trousers Look ElegantFrench women in Paris are also wearing it.
-
Jeans, Who? It Girls Everywhere Are Wearing Boots With This Anti-Denim Trend Right NowIt will also be a fashion person's go-to uniform this winter, too.
-
Just Like That, Suits Go From Boring to Cool When You Swap Button-Downs for This 2025 ReplacementMeet fashion's hardest-working basic.
