Fashion hits and misses for September 2019

By Megan Riedlinger 8:19am PDT, Sep 24, 2019

September is a busy month for your favorite stars! From New York Fashion Week to the Primetime Emmys, there have been plenty of opportunities to show off their fashion sense, and we're here to judge all of it! Wonderwall.com is rounding up this month's best and worst dressed, starting with this unfortunate selection from Gwyneth Paltrow. The star topped numerous worst dressed lists on Emmy night on Sept. 22 thanks to this vintage Valentino design. Though we appreciated the fact that she opted for a dress from 1963, the bizarre strips of fabric dangling from the sleeves converted this otherwise simple black-and-white frock into a fashion disaster. Keep reading to see more of September 2019's celebrity fashion hits and misses!

One of the best dressed celebs on the 2019 Primetime Emmys red carpet on Sept. 22? Zendaya, who arrived in this show-stopping dark green Vera Wang design. The "Euphoria" star's strapless dress started with a sleek lingerie-inspired bodice and gave way to a silk skirt with a thigh-high slit that showed off her matching green Brian Atwood heels.

We were hoping the high-low trend was on its way out, but Brie Larson embraced the questionable hemline at the premiere of "Just Mercy" on Sept. 6 during the Toronto International Film Festival. The fuchsia floral-printed Giambattista Valli frock featured a strapless neckline, a miniskirt in the front and a structured, oversized train at the bottom. Though we weren't crazy about the cut, we do admit we loved the way it showed off her hot pink matching shoes!

A pink moment that worked? Tracee Ellis Ross's dreamy hot pink confection at the Embrace your ish party in Los Angeles on Sept. 17. The Christopher John Rogers design featured a banded waist and exaggerated silhouette with the skirt. She paired it with heels in the exact same pink hue for a standout outfit.

Though we appreciate the fact that Renee Zellweger was paying homage to Judy Garland's Old Hollywood era with this wild red brocade print, we ultimately weren't fans of the bold Oscar de la Renta minidress — complete with an over-the-top bow detail — that Renee wore to the "Judy" premiere on Sept. 19.

We loved the edgy Chanel garb that Kristen Stewart wore to the Deauville American Film Festival on Sept. 14. The star topped her casual white tee-and-shorts combo with a tweed Chanel jacket for an unexpected pairing that totally worked. Bringing a little more flare? Her high white socks and black boots.

Amy Adams arrived at the 2019 Primetime Emmys on Sept. 22 in this snooze-worthy Fendi dress. The frock featured a boring long-sleeved silhouette and a faux-sheer aesthetic, and her uninspired updo and minimal makeup certainly didn't help matters.

Hailee Steinfeld looked ready for fall at the "DICKENSON" premiere in New York City on Sept. 14. We loved her plaid long-sleeved strapless minidress by Balmain — which she paired with the perfect fall shoe: an over-the-knee boot.

Another month, another weird Rita Ora street style moment! This time, the singer mixed stripes and plaid underneath a cropped cream blazer and finished things off with bright yellow runners while out in London on Sept. 20.

Outstanding lead actress in a limited series or movie nominee Joey King attended the Primetime Emmys on Sept. 22 in this standout strapless gown by Zac Posen. The star of "The Act" looked regal in red in the full-skirted confection, which had an adorable detail on the back…

The bow detail on the back of Joey King's Zac Posen dress ensured this look was a hit. The star, who's growing out her hair after shaving her head for her Emmy-nomination role of Gypsy Rose Blanchard, rocked her short tresses in curls and added the perfect Swarovski ruby earrings for the occasion.

Olivia Munn made a case for sequins and lost at the Creative Arts Emmy Awards in Los Angeles on Sept. 15. The actress stepped on the red carpet in this sequined and strapless column design, which also featured floral embellishments that added even more to the busy gown. The shiny selection earned the star a spot on the miss list this month.

Sarah Jessica Parker wore white after Labor Day and won in this three-quarter-length-sleeve confection. We liked the simple bateau neckline and banded waist and the way she kept things simple and stylish with black pointy-toe shoes at the BlogHer19 Summit in New York City on Sept. 18.

We're all for a little leopard print every now and again, but this look on Naya Rivera crossed the line. The star's off-the-shoulder long-sleeved and floor-length dress resulted in a whole lot of the bold animal print… too much, if you ask us! She wore the questionable ensemble to the "Judy" premiere in Los Angeles on Sept. 19 with simple black sandals.

Typically, leather trench coats haven't fared so well on our fashion hits and misses lists, but Sofia Richie pulled this one off! The model rocked a leather trench over a white crop top and leather pants at the Sofia Richie x Missguided Launch Party in Los Angeles on Sept. 18 for a surprisingly cool look.

We actually have no idea what Cuba Gooding Jr. was going for with this getup. The actor attended the "Godfather of Harlem" screening in New York City on Sept. 16 in this bizarre combination of gray overalls, a black shirt, a red leather jacket and shiny black boots.

This sparks joy! Marie Kondo donned this pretty short-sleeved white design, which featured delicate studding and a knot detail at the waist, at the Creative Arts Emmy Awards on Sept. 14.

Who knew such a simple outfit could be such a flagrant miss? Emily Ratajkowski opted for a white tank top and jeans with a brown belt for an outing in New York City on Sept. 16, but when it came time to add shoes, she somehow converted this otherwise inoffensive outfit into a disaster. She picked mustard yellow knee-high boots by Rag & Bone to wear with her classic look and earned a fashion citation in the process.

Elizabeth Reaser rocked one of our favorite underrated color combos — bright yellow and pink — as summer wound down. The star donned a long-sleeved, midi-length frock with a tie detail with a pair of gorgeous hot pink strappy sandals for a cheery look at the "Transparent" finale event in Los Angeles on Sept. 13.

We're not quite sure what Julianne Hough was going for with this drapey gold design. But the plunging neckline and sky-high hemline on her Michael Costello dress at the "America's Got Talent" finale on Sept. 18 combined for a major fashion miss.

Irina Shayk stepped out during Milan Fashion Week in this killer Versace combo — a red turtleneck sweater, a black miniskirt complete with Medusa-adorned buttons and a tiny bag. She complemented her couture with a pair of Dr. Martens boots to stay comfy while shopping on Sept. 19.

To say we weren't wild about Constance Wu's Georges Hobeika minidress at the "Hustlers" premiere at the Toronto International Film Festival on Sept. 7 would be an understatement. The tacky piece of couture featured a plunging neckline and an over-the-top bow detail that fell all the way to the floor, making it our least favorite look of the month.

Gorgeous in green! Dakota Johnson rocked this beautiful Valentino gown with a ruffled off-the-shoulder cut and tied belt detail at a party hosted by The Hollywood Reporter during the Toronto International Film Festival on Sept. 7. Aside from picking one of our favorite gowns of the month, Dakota also rocked the perfect hairstyle to match. See it next…

We loved Dakota Johnson's artfully messy topknot, which contrasted well with that fabulous feminine off-the-shoulder gown. Equally gorgeous? Her plum lip shade.

Oh, Suki Waterhouse. The model-actress attended the DKNY turns 30 party during New York Fashion Week in, well, this DKNY mess. The baggy wrinkled tan pants over top logo-detail briefs paired with a cropped long-sleeved white T-shirt left a lot to be desired. Making matters worse? The way she added those funky heeled boots to this otherwise casual mix.

Jennifer Lopez has served up some phenomenal looks while out promoting her new flick "Hustlers" this month (seriously, check them all out!). Our favorite? This white feathered Maison Valentino design she sported while arriving at the SiriusXM studios in New York City on Sept. 10. We can't decide which we love more — that dreamy, feminine frock or those stunning pink velvet platform heels.

The long-sleeved, floor-length dress that Keke Palmer wore to the "Hustlers" premiere afterparty during the Toronto International Film Festival on Sept. 7 left us scratching our heads. From the taupe halter layer underneath (is it a bra or a tank top?) to the nearly off-the-shoulder cut of the multicolored slinky knit dress, this look straddled the line of dressy and casual and earned a fashion miss in the process.

Could Zendaya be any cooler?! The star wore this killer black slip dress with a black leather moto-trench coat to the Marc Jacobs show during New York Fashion Week on Sept. 11. She added some sparkle in the form of drop earrings and completed her look with tights, socks and boots.

We always like Kristen Stewart's unique Chanel choices, but we couldn't get behind this crop top and trouser combo. The star wore this long-sleeved houndstooth plaid top with wide-legged pants and an odd-shaped tie to the "Seberg" premiere during the Toronto International Film Festival on Sept. 7.

Obsessed! Serena Williams served up a stellar look at the premiere of "The Game Changers" in New York City on Sept. 9. The tennis superstar's white spaghetti-strap slip dress fit her like a dream and the addition of a pop of color via those pointy-toe yellow pumps was perfection.

Though it was fitting for the occasion — the Savage x Fenty fashion show on Sept. 10 — we weren't wild about Kacey Musgraves' exotic ensemble. The green zebra-print coordinates paired with a lilac crop top (or maybe it's a sports bra?) certainly made a statement, just not a good one.

Lili Reinhart looked like a real-life angel in this unique Rodarte gown at a "Hustlers" premiere afterparty during the Toronto International Film Festival on Sept. 7. We loved the quirkiness of this ethereal gown from the lace trimmings to the Rodarte statement belt. Next up? A closer look at those dramatic sleeves…

Upon closer inspection, you can see the detailing that went into the top of Lili Reinhart's Rodarte confection. From the eyelet detailing to those dramatic floral-shaped adornments on the shoulders that gave a wing-like effect from afar, we were fans of many elements of this funky frock.

Almost, but not quite, Jessie James Decker! The star attended a party for her fashion line, Kittenish by Jessie James Decker, in New York City wearing a look that was nearly a hit but ultimately missed the mark. Though we liked the orange hue of her suit, the sheer black top she added wasn't the greatest choice, and those strappy sandals were a terrible way to complete this ensemble.

Lucy Hale's Oscar de la Renta look stood out at the designer's show during New York Fashion Week on Sept. 10. The star paired a silky black blouse with mustard yellow wide-legged trousers and added more yellow in the form of a crocodile-skin bag. She completed her look with stark white pointy-toe heels.

What's going on here, Shailene Woodley? Her bizarre Louis Vuitton look featured a purple cap sleeve, cut-outs, a black belt, pockets and stripes along the miniskirt, and if that wasn't enough conflict for you, she paired it with shiny combat boots. She wore this awful ensemble to the "Endings, Beginnings" premiere during the Toronto International Film Festival on Sept. 8.

Sometimes simplicity makes the biggest statement. We adored Rooney Mara's black Hiraeth gown with a sweetheart neckline trimmed in lace, which she paired with elegant pointy-toe black shoes at the "Joker" premiere in Toronto on Sept. 9.

Another miss this month? The silver spaghetti-strap Rodarte gown that Scarlett Johansson wore to the "Jojo Rabbit" premiere during the Toronto International Film Festival on Sept. 8. We weren't fans of the pleating, gathering and high-low hemline of the frock — or the way she paired it with super matchy-matchy silver sandals.

Michelle Dockery looked stunning and statuesque in this golden Galvan gown. The one-shouldered sequined confection was gorgeous and glimmering on the red carpet at the "Downton Abbey" movie premiere in London on Sept. 9.

Yikes! Jon Hamm arrived at a reception for "Joker" during the Toronto International Film Festival on Sept. 10 in this odd ensemble — a maroon shirt and brown pants topped with a navy buttoned-up cardigan and completed with stark white sneakers.

Heather Graham donned this lovely dual-hued, one-shouldered gown at the premiere of "The Rest of Us" at the Toronto International Film Festival on Sept. 6. The pretty frock featured a ruffle detail at the neckline and went from a bold teal bodice to a deep blue full-length skirt.

We adore Erika Jayne as much as any other "The Real Housewives of Beverly Hills" devotee, but this look she chose for the Marc Jacobs show during New York Fashion Week missed the mark. Her long-sleeved, floor-length floral frock might have been fine on its own, but she lost us when she topped it with a bizarre feathered and embellished cape.

Emily Blunt's bold red-brown suit matched her lip perfectly at the Tory Burch show during New York Fashion Week on Sept. 8. We loved the way the star added a white blouse, tan bag, wide gold hoop earrings and a sleek updo to make this look even more glamorous.

If not for those iridescent purple tights, we would have loved this colorful getup on Katherine Schwarzenegger. Unfortunately, the striped ensemble she wore to the Kate Spade show during New York Fashion Week on Sept. 7 landed among the misses.

Jessica Biel selected this stellar menswear-inspired getup for the "Limetime" premiere during the Toronto International Film Festival on Sept. 6. She paired a pinstriped black suit with a printed black top and added pointy-toe black heels and an updo for a sharp red carpet look.

Priyanka Chopra taught us a valuable lesson while stepping out in Toronto on Sept. 7 — there is such a thing as too much suede. The star opted for different hues of brown suede for her odd monochromatic ensemble made up of a collared blouse, a midi-length skirt and heels and ended up earning herself as serious fashion citation in the process.

Jennifer Lopez rocked ruby red at a party during the Toronto International Film Festival on Sept. 7. The superstar sported this stunning sequined Elie Saab number, which featured a plunging neckline and asymmetrical hem and paired it with matching red heels.

We loved seeing Little Big Town's Kimberly Schlapman at New York Fashion Week! But we didn't love the outfit she wore to the Ryan Roche show on Sept. 11 nearly as much. The music star's outfit — a white duster coat, a white ruffled tank, high-waisted jeans and knee-high white boots — seemed better suited for a country music concert than a fashion show.

Suits were everywhere during New York Fashion Week! Kate Hudson jumped on the trend at the Michael Kors Collection Spring 2020 Runway Show on Sept. 11 in this chic houndstooth version, which she paired with a casual white top and chunky black heeled boots.

We're all for a good Canadian tuxedo moment, but Sheryl Crow's attempt was disastrous. The singer attended a Spotify event in Nashville on Sept. 10 in this distressed denim jacket, embellished jeans and denim shoes — an instant fashion miss.

Though multi-colored leopard print doesn't sound like it would work on paper, Constance Wu proved that the animal motif in red, white and blue actually looks lovely. She paired her wild minidress with a pair of cherry red heels to add a dash more color at an AT&T event at the Toronto International Film Festival on Sept. 8.