24 Unforgettably Extra Outfits Debra Messing Wore on Will & Grace 

By Samantha Simon
Sep 28, 2017 @ 12:45 pm
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From 1998 through 2006, we tuned in to Will & Grace like clockwork on Thursday nights. The series offered witty one-liners, top-notch physical comedy, and onscreen friendships unlike any we had seen on TV before. Of course, we’d be lying if we said we weren’t also tuning in to see what Grace Adler was wearing. And when it came to her wardrobe, she never failed to surprise us. The interior designer, played by Debra Messing, was as relatable as characters come. She constantly struggled to find love, she was totally neurotic, and she often fell victim to the latest fashion trends. 

Of course, it’s worth noting that at the time, many of Grace’s ensembles were considered to be totally stylish. But every now and then, she threw us for a loop with one of her unconventional looks. Her biggest fashion critic was her assistant, Karen Walker (played by Megan Mullally), who never approved of Grace’s outfits. And she didn’t feel the need to suppress her thoughts on the matter. Instead, she ripped apart Grace’s patterned tops:

Her ruffled tops:

And even her dresses:

Really, the list goes on. But Karen’s assertions about Grace’s looks weren’t always warranted. After all, Grace was just testing out the best trends that the late ‘90s and early aughts had to offer, and we respect her for that.

With the Will & Grace revival set to premiere tonight at 9 p.m. ET on NBC, we’re anticipating many more over-the-top looks to be headed our way. So in honor of the major TV milestone, we’ve rounded up 24 of Grace’s most unforgettable looks to date. Scroll down for a fairly dated—but never dull—walk down memory lane.

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1 of 24

The Graphic Top-Headscarf Combo

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Grace was far from understated in the series’ pilot, and she paired a tropical tank with a statement necklace and headscarf just to prove it.

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2 of 24

The Furry Red Coat

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In another look from episode one, Grace channeled Elmo in this fluffy coat that simultaneously embodied everything we loved and hated about ‘90s trends.

3 of 24

The Endless Supply of Pearls

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Grace often wore pearls, because she’s classy, duh. But she kicked her obsession into high gear when pairing these long layered strands with a choker necklace and a button-up blouse during season one.

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4 of 24

The Knit Top Hat 

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Grace didn’t have time to blow-dry her hair during this season one episode, so she showed up to work in…well, in this. Needless to say, Karen did not approve.

5 of 24

The Matchy-Matchy Orange Look

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Grace never let her red hair limit her color palette, wardrobe-wise. Towards the end of season one, she paired this shiny jacquard dress with a matching pair of bright orange shoes.

6 of 24

The Red Turtleneck and Water Bra

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This is an iconic Grace Adler moment right here, folks. Back in season two, Grace wore a “hydra-bra” to make her breasts look larger while trying to impress a guy who had never given her the time of day in high school. Unfortunately for Grace, the water-filled undergarment sprung not one but two leaks while attending her former (and current) crush’s gallery opening, giving us one of the show’s most all-time hilarious scenes.

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7 of 24

The Cow-Print Skirt 

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When Grace walked into her office in this cow-print skirt back in season two, Karen didn’t miss a beat. After taking one look at it, she said, “Got skirt?” If the skirt wasn't enough of a bold style move, Grace wore it with a bright orange t-shirt.

8 of 24

The Bellychain

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When attending a banquet for Will’s dad’s company in season two, Grace opted for a matching set that would actually be considered fairly chic today. “This took all afternoon—it was like building a boat,” she told Will of her final look. The crop top and skirt aren’t over-the-top on their own, but because it was 1999, she threw on a bellychain-style belt to complete her look. It’s ok, Grace. We all owned one. 

9 of 24

The Striped Halter Top

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Grace was a fan of halter tops, and none was as bold as this striped number she wore in season two. Of course, no look is complete without accessories, so she wore matching bracelets, to boot.

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10 of 24

The Pink Go-Go Boots

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Ok, they’re not actually go-go boots. But that’s what Karen called them when she told Grace that she thought the footwear was making her “feel like an idiot” back in season two. If she’d paired them with a neutral outfit, the boots wouldn’t be so bad. But with the matching skirt it’s a bit blinding.

11 of 24

The Snakeskin Pants

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If anyone is going to wear snakeskin-printed pants proudly, it’s Grace Adler. Luckily, she kept her look in check by pairing them with a simple black mock-turtleneck and black booties in the show's second season. But it was still a bold style statement. 

12 of 24

The Layers Upon Layers

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Grace was invited to have a threesome with her ex-boyfriend and his current girlfriend in season three, but instead of turning them down because she was uncomfortable, she decided to go through with it. Only when she showed up, she was wearing a ton of layers—a coat, jacket, turtleneck, and a sweatshirt. It was the most ridiculously over-the-top ensemble she ever put together.

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13 of 24

The Incognito Look

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In season four, Grace began seeing yet another former high school crush—only this one was serving time behind bars. After telling Will that she was heading to jail for a visit, he said, “You’re like one of those women in a polka-dot dress and a floppy hat that bakes brownies for serial killers.” After insisting that there was “nothing weird” about what she was doing, Grace topped off her own polka-dot dress with a floppy hat and sunglasses and walked out.

14 of 24

The Giant Fur Sleeves

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After returning from her honeymoon in season five, Grace chose a patterned top with fur bell sleeves to feel ultra-glamorous while showing off her vacation photos. Because nothing screams “I just got back from a week in the Caribbean” like hibernation-friendly sleeves for winter.

15 of 24

The Wide-Leg Brown Leather Pants

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Grace always had a penchant for leather, but these brown pants from season five were especially memorable. It seemed that Grace got her seasonal signals crossed, pairing the winter- or fall-appropriate wide-leg trousers with a tropical-print summery tank top. The result? A slightly confusing—but totally Grace-like—look.

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16 of 24

The “Serious Interior Designer” Look

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Grace might have been trying a bit too hard to look the part of an interior designer with this outfit in season five. Her low-cut LBD was a bit dramatic for work on its own, but paired with lace-up sandals, a layered black choker, and cat-eye glasses, she was really trying to get her new client to take her seriously.

17 of 24

The Red Leather Bucket Hat

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In season six, Grace sported a red leather bucket hat while keeping Will company as he waited in line for Barry Manilow tickets. While the rest of her outfit was entirely black, it was anything but plain. Under her coat, Grace wore a fur-trimmed top (or sweater, we’re honestly not even sure about this one) that added a lot of…fluff to her overall look.

18 of 24

The Plunging Black Swimsuit

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For an outing on Karen’s yacht in season six, Grace chose a plunging black bathing suit that surely required some fashion tape to stay in place. It was an overly sexy look for a boat excursion with friends, but she rocked it happily.

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19 of 24

The Lime Green Coat

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Grace loved a statement coat, and she proved time and time again that she wasn’t afraid to wear color. So while it’s not exactly a shocker that she stepped out in this shiny lime green trench coat in season seven, there’s no denying that the piece itself is shocking.

20 of 24

The Orange Jumpsuit

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In season seven, Grace wore an orange jumpsuit—complete with matching scarf worn as a belt—for a day of shopping at Barneys with Jack and Will. But after she climbed an entire display wall of jeans to find the exact pair she wanted and, naturally, fell down, Grace went home with an unwanted accessory: a neck brace.

21 of 24

The Impractical Airplane Attire

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When Will and Grace were traveling to London for a weekend in season eight, they just so happened to run into Grace’s ex-husband, Leo, on their flight. Luckily, before her ex spotted her, sweatpants-clad Grace managed to find a party dress and heels in her carry-on. She quickly put herself together in the airplane bathroom and emerged looking way overdressed, but plenty confident—and Leo took note.  

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22 of 24

The Blue Velvet Suit

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Grace wore a blue velvet suit to celebrate Christmas with Will’s family in season eight. It was holiday and seasonally appropriate, but by pairing it with a matching blue ruffled blouse and gold statement earrings, the look quickly became extra. 

23 of 24

The Conductor Hat

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We thought that Grace’s hat habit was behind her, but in season eight, she broke out this poofy bad boy, taking her look to new heights of extra. And her bell-bottom jeans certainly sealed the deal.

24 of 24

The Sound of Music Costume

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A huge fan of the Sound of Music, Grace got fully into character as Maria to attend a sing-along event in season eight. “Do you think people can tell I’m Maria, even though I don’t have my Captain Von Trapp?” she asked Karen, who assured her that she looked the part and tossed a few insults her way in the process.

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