Would You Still Wear It? The Jackie O Dress

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For today’s installment of our new semi-regular feature, “Would You Still Wear It?”, we’re looking at the classic Black Halo sheath dress, the Jackie O. I’ve pictured it above in three iterations: the original, the jumpsuit, and the most modern version with a lower hemline (the Jacqueline). Would you still wear the Jackie O dress in 2026? Would you wear it to the office, save it for a work event, or consider it too dated?

(In our last installment, we pondered whether J.Crew’s Going Out Blazer is dated.)

The History (And Evolution) of the Black Halo Jackie O Dress

I just looked it up: the Jackie O dress predates the blog: it was introduced in fall 2006. According to the lore,

The Jackie O Dress was first introduced into the wardrobes of contemporary women and celebrities in Fall 2006. Black Halo designer Laurel Berman, claims that the origin behind the Jackie O was inspired by her search for a solution to flawlessly execute the high waisted pencil skirt with tucked in camisole blouse look, creating the flattering illusion of both length and slimming the waist region when worn.

(See also.) I must say… I have never once looked at the dress and thought I saw a camisole tucked into a skirt, at least certainly not like that old Ted Baker dress. But maybe that’s me. (Did we even have camisoles like that back then?) It’s worth noting that they also make a Jackie skirt.

The jumpsuit version of the dress was introduced in 2019. All of the versions have sometimes been available with sleeves, without sleeves, in different colors, and in different fabrics. All three versions are still on the market today.

Is the Jackie O Dress Stuck in the Aughts?

I’ve seen some influencers just cackling over the dress being stuck in the aughts, much like the bandage dresses from back then. But the Jackie dress has been consistently sold all these years, with new fabrics and colors regularly. Even during the pandemic, if I’m remembering correctly! So there is still a market.

(Although! According to Marie Claire, bandage dresses are coming back in style… including a longer version.)

Is the Jackie O Dress Too Recognizable a Look?

It is definitely a distinct look, although more expensive brands like Roland Mouret and Victoria Beckham have both had similar options. I can see how a celebrity couldn’t wear it too regularly (although Meghan wore it in 2018!).

The Newest Jackie O Dress: The Jacqueline

As a lot of readers have noted, hemlines at or near the knee tend to look a bit dated these days… so the longer length is welcome. The brand reimagined the Jackie O dress as the Jacqueline in fall 2025, so it’s been around for about a year.

The brand currently has the Jacqueline available in seven colors, in sizes 0-14 for $390. You can also find the classic Jackie O available in five colors, sizes 0-18, for $375. (Nordstrom also carries multiple colors of the Jackie O, the Jacqueline in beige, and the jumpsuit in black.)

My $.02

I’ve always liked the Jackie O look. It’s always been a bit va-va-voom for most offices, but I think for a speaking engagement or a desk-to-dinner kind of day it works and is a good look.

The Jacqueline dress feels like it’s more solidly in the cocktail camp, largely due to the off-the-shoulder neckline.

I would consider them all classic looks.

Readers, what are your thoughts — is the Jackie O a classic? Dated? Not for the office?