Katie Holmes Keeps Breaking Fashion Rules...and Here’s Why That’s a Good Thing

Unless you spent the last year residing under a rock, you’ve probably witnessed Katie Holmes undergo one of the best fashion glow-ups we’ve seen in a long time. While her style wasn’t terrible before 2019 rolled around, it also wasn’t exactly what we’d call memorable. 

But all that’s changed, because Ms. Holmes has officially reached the status of “fashion icon worth stalking for hours on the internet.” And it’s not because she’s suddenly stepping out in head-to-toe Dior Haute Couture looks, but because she’s been breaking almost every fashion rule in the book—and looking fantastic while doing it. Like wearing socks with sandals to a fancy fashion show or rocking an unbuttoned sweater with a matching bra underneath.

See, in eschewing the unspoken edict of capital-F Fashion, Holmes is letting her own personality shine through, turning her rebellious acts into sartorial statements worth talking about. Here are five of Holmes’s best outfits from 2019 that we won’t be forgetting anytime soon.

Katie Holmes Just Wore this Summer's Most Daring Pair of Overalls

socks and sandals
Jacopo Raule / Contributor/ Getty Images

Socks & Sandals

Usually the combination of socks and sandals is relegated to stressed out dads at Disney World, but look how happy Holmes looks in her contentious footwear situation.

Why does it work?

Holmes made dainty a theme out of this footwear choice and her dedication to that pays off, especially when sitting front row at a fashion show in Milan. The sheer Swiss dot sock in a nude shade pairs seamlessly with her sandals, that also happen to feature a delicate leather bow. When paired with her fiery red silk dress and blazer from Fendi, the neutral footwear serves to ground an otherwise loud outfit.

katie holmes bra
Astrid Stawiarz/Getty Images

Matching Her Bra To Her...sweater?

While we can’t recommend wearing a cashmere bra under an open cardigan to work (or really anywhere but the comfort of your living room), you have to admit that Holmes is owning this unlikely outfit. (See the pic here.)

Why does it work?

Holmes said it best when Vogue asked her about the knit set from the luxe brand Khaite, that FYI, she bought for herself: “It was very comfortable and easy and I think they [Khaite] do such a good job with creating beautiful luxury items. They are very accessible and classic so you can have it for a long time, and I like to shop that way. I’m not always buying new stuff and I can wear it again.” Here’s to hoping we see Holmes rock her cool cashmere cardi time and time again.

katie holmes
Gotham / Contributor/ Getty Images

Mis-matched Accessories

Let’s go ahead and address the star of this outfit: That impeccably fitted suit from Gabriela Hearst that’s served up in a positively mesmerizing shade of midnight blue. Now, let’s move onto the fact that her pointy heels and simple leather clutch are just one shade apart.

Why does it work?

These accessories are both neutrals and so they’re absolutely not the focal point of this getup. In fact, they’re more like supporting actors that let the suit’s brilliance stand on its own. The fact that they’re mismatched means only two things: 1) Holmes is an imperfect human, just like us and b) she’s letting the most important feature of her look take center stage.

evening gown
Thomas Niedermueller/Life Ball 2019 /Getty images

Keeping An Evening Gown Casual

It can feel close to impossible to truly feel like yourself in formal wear. But is it a faux pas to pair a flowing frock with super casual accessories? No!

Why does it work?

A curated selection of delicate jewels—like the pendant and choker that she’s layered around her neck—allow Holmes’s low-key personality to shine on the red carpet for the Life Ball in Vienna. At once casual and playful, these everyday baubles make her glittery Missoni ballgown feel a little bit less precious. And the fact that her hair is stick straight (a style that she seems to wear on the reg), makes Holmes seem even more comfortable on the red carpet. That’s a feat we can all appreciate.

lace and florals
Robert Kamau / Contributor/ Getty Images

Mixing Lace & Florals

These patterns just don’t go together, you might be thinking. Which, is not untrue. But there’s something so endearing about this clashing moment.

Why does it work?

The dress and Dolce & Gabbana booties sit on opposite sides of the sartorial spectrum. One is floral, a touch dowdy and looks like it’d be the most comfortable sack ever. The other is made from one of the sexiest fabrics known to mankind and cut in a silhouette that just oozes sex appeal. And you know what they say? Opposites attract, which is certainly at play here, when Holmes was on her way to the American Ballet Theatre spring gala. The sultry peep-toe lace booties add a much-needed va-va-voom factor to the floral dress and they simply feel so much more creative than a pair of basic black pumps would. Brava for taking such a risk, Ms. Holmes. It definitely paid off.

dena silver headshot

Fashion Editor

From 2019-2021 Dena Silver held the role of Fashion Editor covering product recommendations, trends, and what you should be shopping this season.