Vivian’s 10 Best Outfits In Pretty Woman

With 2020 nearly upon us, Pretty Woman is just about ready to turn 30 after its initial release in March of 1990. It’s a film that’s touched our hearts, and every time we go back to it, we always notice something new. The film serves as a more modern take on the classic romance tale that features two lovers born on different sides of the track.

While Edward Lewis is an influential businessman, already ensnared by the trappings of corporate America, Vivian Ward is a prostitute he befriends one night after getting himself stranded in LA’s infamous red-light district. While Edward’s transformation throughout the film is largely psychological, Vivian’s is mostly physical, and the movie chooses to represent her attainment of a better life through the clothes she wears.

For a change of pace, let’s highlight ten of Vivian’s finest fits throughout the course of this feature film. With the Christmas season upon us, we’re sure you too can find lookalike pieces to recreate some of these outfits to unlock your inner Vivian Ward, taking full control over your circumstance and your body, just as she did.

10 Robes Aplenty!

Although many may not consider bathrobes an outfit, it’s hard to look at Vivian in one and not reconsider. Vivian is first seen in a bathrobe the morning after her first night with Edward. She’s seen sporting a more natural look without her heavy eyeliner, lipstick, and short blonde wig from the night before.

The robe isn’t revealing in the slightest and allows her to stroll through a five-star hotel with such a carefree swagger that we’d have expected only out of someone who actually purchased a hotel suite themselves. Towards the end of the film, she dons a black silk robe with flower prints, maintaining the perfect balance between relaxation and elegance.

9 The Red-Light District Fit

The very first time we see Vivian, she’s stalking the red-light district of LA, looking for her next paycheck in the form of some desperate guy. This outfit has all the signs of an independent rebel: tattered knee-high leather boots, an oversized pink jacket, a short blue skirt connected to a white sleeveless crop top, complete with a blonde wig and a dark octagonal cap.

We later learned that she can opt to ditch the jacket for a more provocative appearance when approaching potential customers. Anyone who saw her in this outfit could immediately tell how she made her money, and although it isn’t worth nearly as much as the other outfits on this list, the important thing to remember is that Vivian chooses to wear this outfit, like anything else she puts on her body. It may be revealing, but it’s only as much as Vivian wants her customers to see.

8 The “Green-Light District” Fit

This outfit is an interesting take on what we first saw her wearing in the red-light district, with her signature blue skirt being the only constant that remained from the last entry.

Instead of her knee-high boots, we’re almost certain Edward forced her into a pair of heels. Covering her upper torso is an oversized dress shirt tied in the front, and something tells us it’s just an extra one of Edward’s.

7 Striped Short Pants Suit

In the montage of Vivian trying on several different outfits, one, in particular, stands out: a casual short pants suit that was both simple and unique. The stripes lining the outfit was the first thing to catch our attention, but upon further inspection, we noticed the mesh-like material that the sleeves were made out of.

She wore it later in the film during a casual date with Edward at the park. Let’s just all be glad Vivian didn’t get any tomato sauce anywhere on this fabulous fit when that pizza popped up in the middle of her shopping spree.

6 Barb’s Quickie Grill Date Dress

After Edward took Vivian to see the opera, the two quickly began to grow closer. What better way to illustrate this onscreen than with a classic montage? At one point, the two are shown in a streetside diner that they’re both dressed a little too fancy for, Vivian in particular.

She’s wearing a stunning magenta off-shoulder dress that we only wish got more screentime. We only see this dress for a few brief seconds, and we don’t even get the chance to see what kind of shoes she’s wearing with it! Edward really needs to step his fashion game up a bit if Vivian starts wearing stuff like this to a hole in the wall diner!

5 All-Black Cocktail Dress

This was the first time we’d seen Vivian clean up in the film, and just like Edward, we were blown away. The neckline of the dress and the black gloves pull it all together, and Vivian’s accompanying ponytail and light makeup definitely made it hard for Edward not to catch feelings that night.

Fit for a fancy dinner or upscale jazz club, Vivian was dressed to impress, but we couldn’t help notice that creepy man staring her down at dinner. He is lucky one of those clams that slipped from Vivian’s hands didn’t poke him in the eye…

4 Salmon-Colored Blazer

Vivian debuted her salmon-colored blazer fit the afternoon she met up with Kit De Luca. Completing the look with a pair of dark shades, she looked like she was a boss interviewing Kit for a summer job rather than her best friend.

This outfit gave us some serious Aunt Becky from Full House vibes, and we loved seeing Kit’s reaction to her friend dressing from a forlorn hipster to an absolute boss! Later on, she takes off the blazer for a more casual look, letting the belt and sleeveless blouse really shine. We definitely want to know where we can get this amazing outfit, minus the outdated shoulder pads of course…

3 Long Navy Blazer and Blue Jeans

Our favorite outfits are the ones that speak to Vivian’s personality more than they do Edward’s bank account. Vivian’s last outfit is a trailing navy blazer with blue jeans.

Not only is it simple, but it makes Vivian look almost like a distinguished professor, which is ironic since she gave Kit money under the alias of the “Edward Lewis Scholarship Fund.” We’re glad Vivian lets her own individual style shine through the clothes she wears when she’s not trying to impress Edward’s business partners.

2 The “You Work On Commission” Dress

From the first time Vivian got turned away from that designer clothing store, we couldn’t wait for her to get her revenge, and she chose to do so in an outfit that broke several necks on the Los Angeles summer streets.

The wide-brimmed hat and gloves give her a distinguished aura, and we wouldn’t be surprised if we found out that she borrowed this from Meghan Markle’s closet.

1 Ruby Red Gown

It was a hard call to make, but we feel like the bright red dress Vivian wore the night she saw her first opera was her best outfit in the entirety of Pretty Woman. As if the dress wasn’t perfect before, the $250,000 ruby-studded necklace Edward gave her was the icing on the cake. The moment she put on this dress marked the moment her emotional walls began to break down and she not only began to fall for Edward, but he also becomes more determined to win her over with the trappings of the bourgeois.

Vivian becomes visibly more comfortable wearing such high-end outfits at this point in the narrative, with Edward even commenting that she’s fidgeting a lot less. Yet despite enduring so many dramatic wardrobe changes, fans of Pretty Woman are always glad to know that at her core, Vivian never changes, no matter what she chooses to wear. She’ll always be the same Vivian Ward we came to love, red-light district fit or ruby red gown.

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