Lady Gaga’s Most Daring Looks in Pleaser Heels During Final Concert Week With Tony Bennett

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In August 2021, longtime friends Lady Gaga and Tony Bennett reunited in New York City for One Last Time, a two-night live concert series celebrating the jazz icon’s 95th birthday and their decade-long musical partnership.

Performing together for the final time, the duo delivered timeless classics to a sold-out audience at Radio City Music Hall — with notable guests including Bon Jovi and former President Bill Clinton in attendance.

The emotional event also marked Bennett’s final public performance following the revelation of his 2016 Alzheimer’s diagnosis.

Tony Bennett and his wife Susan Crow leaving their NYC apartment to perform with Lady Gaga at Radio City Music Hall on August 3, 2021Tony Bennett and his wife, Susan Crow, leaving their NYC apartment to perform with Lady Gaga at Radio City Music Hall on August 3, 2021 (Credit: Avalon / WENN)

In addition to the concert, Lady Gaga and Tony Bennett also announced their second collaborative album, Love for Sale, which was scheduled for release on October 1, 2021.

A follow-up to their 2014 Grammy-winning album Cheek to Cheek, the 10-track project is a tribute to legendary composer Cole Porter. Recorded between 2018 and 2020, it is widely considered Tony Bennett’s final studio album.

A Strawberry Statement: Gaga Wows in Christopher John Rogers Dress

Heading to Radio City for the final day of their concert, Lady Gaga showed off her eccentric sense of style in a quirky dress from Christopher John Rogers.

Lady Gaga arriving at Radio City Music Hall for One Last Time concert with Tony Bennett on August 5, 2021Lady Gaga arriving at Radio City Music Hall for One Last Time concert with Tony Bennett on August 5, 2021 (Credit: Mega / WENN)

It features the designer’s signature strawberry silhouette—a fitted strapless bodice juxtaposed with a sculptural midi skirt underpinned by layers of tulle to keep its shape.

The seersucker plaid number also has internal boning and a slit at the back for comfort.

Lady Gaga wears a strawberry-shaped plaid midi dress from Christopher John RogersLady Gaga wears a strawberry-shaped plaid midi dress from Christopher John Rogers (Credit: Mega / WENN)

Towering in Pleasers: Gaga’s Sky-High Boot Obsession

But while the dress was a scene-stealer on its own, Lady Gaga’s trademark towering platform heels also attracted attention.

Lady Gaga pairs her unique dress with towering platform boots from Pleaser ShoesLady Gaga pairs her unique dress with towering platform boots from Pleaser Shoes (Credit: Mega / WENN)

The A Star Is Born actress made a dramatic exit from her NYC hotel in a pair of white Pleaser “Flamingo” 1050 boots. These mid-calf lace-up boots boast 8-inch sky-high heels and 4-inch platforms.

The Pleaser Shoes Flamingo boots have 8-inch sky-high heels and 4-inch platformsThe Pleaser Shoes Flamingo boots have 8-inch sky-high heels and 4-inch platforms

Showing off her arm tattoos, the Mother Monster further glammed up with a sleek high bun, rosy blush, and glossy lip shade. She then rounded out her look with pearl drop earrings and a pair of cat-eye sunglasses.

Lady Gaga accessorizes with pearl drop earrings and glams up further with a high bun and red lip glossLady Gaga accessorizes with pearl drop earrings and glams up further with a high bun and red lip gloss (Credit: Mega / WENN)

Sleek in Sportswear: Gaga’s Athleisure Rehearsal Look

On Wednesday, Lady Gaga was photographed wearing the same towering boots for a rehearsal in Midtown Manhattan.

Lady Gaga leaving Radio City Music Hall after a rehearsal for One Last Time live concert on August 4, 2021Lady Gaga leaving Radio City Music Hall after a rehearsal for One Last Time live concert on August 4, 2021 (Credit: Mega / WENN)

Elevating an athleisure outfit, Lady Gaga teamed her boots with a pale blue sports set from Marc Jacobs.

Open about her hip surgery, the multiple Grammy-winning star flaunted her curves in a $95 “The Bandeau” jersey crop tank top and matching $165 “The Sport Shorts” high-rise biker shorts.

Lady Gaga shows off her curves in a pale blue Marc Jacobs crop tank top and biker shortsLady Gaga shows off her curves in a pale blue Marc Jacobs crop tank top and biker shorts (Credit: Mega / WENN)

Keeping the look sleek and chic, Lady Gaga pulled her tresses into a center-parted bun and shielded her eyes behind a pair of Dita Eyewear “Erasur” angular sunglasses.

She also accessorized with $350 Jennifer Fisher gold hoop earrings and carried a $2,150 Mark Cross Madeline Mini Lady bag in quilted white leather.

Lady Gaga wears a center-parted bun with Jennifer Fisher gold hoops and Mark Cross mini bagLady Gaga wears a center-parted bun with Jennifer Fisher gold hoops and a Mark Cross mini bag (Credit: Mega / WENN)

Avant-Garde Vibes in Loewe and More Pleasers

Earlier in the day, the 35-year-old singer arrived at the iconic venue in avant-garde fashion. She wore the same white patent Pleaser boots this time with a periwinkle blue dress from Loewe.

Lady Gaga arrives at Radio City Music Hall to rehearse for a live concert with Tony BennettLady Gaga arrives at Radio City Music Hall to rehearse for a live concert with Tony Bennett on August 4, 2021 (Credit: Mega / WENN)

The Poker Face hitmaker pulled out all the stops in her seersucker button-up dress, boasting draped sleeves and a pleated bubble skirt on the back.

The frock, styled with a waist-cinching slim brown belt, showed the singer’s toned legs, thanks to the front A-line hem that fell a few inches above her knees.

Lady Gaga looks avant-garde in her Loewe periwinkle blue dress with billowing sleeves and a bubble skirtLady Gaga looks avant-garde in her Loewe periwinkle blue dress with billowing sleeves and a bubble skirt (Credit: Mega / WENN)

Wearing a coiffed updo, Lady Gaga accessorized with $170 Agmes Gertrude stud earrings, her Dita sunnies, and a Mark Cross mini bag.

Lady Gaga wears a perfectly coiffed French twist updoLady Gaga wears a perfectly coiffed French twist updo (Credit: Mega / WENN)

Boss Lady in Pinstripes: Gaultier Power Dressing

On Monday, Lady Gaga toned down her forward-looking outfits and opted for a chic executive look in a white pinstripe suit from Jean Paul Gaultier.

Lady Gaga leaving her hotel in New York City on August 2, 2021Lady Gaga leaving her hotel in New York City on August 2, 2021 (Credit: Mega / WENN)

The boss lady wore a double-breasted blazer with wide-leg pants that hid her Pleaser Shoes “Xtreme 1020” boots in nude vinyl.

These boots look similar to her Flamingo boots. They also have a front lace-up closure but with 7-inch heels and about 3-inch platforms.

Lady Gaga channels her inner boss lady in Jean Paul Gaultier pinstripe suitLady Gaga channels her inner boss lady in Jean Paul Gaultier pinstripe suit (Credit: Mega / WENN)

Continuing with her business-ready look, Lady Gaga carried a $1,190 Symmetry Pochette leather tote from Savette.

She then accessorized with $370 Agmes Bubble hoop earrings, a $1,800 Edward Avedis “Clara” diamond ring, and a pair of $450 Valentino “Vlogo” Signature Acetate cat-eye sunglasses.

Lady Gaga looks neat with her updo, Valentino sunnies, and Savette Symmetry Pochette leather toteLady Gaga looks neat with her updo, Valentino sunnies, and Savette Symmetry Pochette leather tote (Credit: Mega / WENN)

Retro-Chic in Rodarte Polka Dots

On her way to rehearse at Radio City Music Hall on Saturday, Lady Gaga opted for a retro mid-century look, wearing a black-and-white polka-dot dress from Rodarte.

The wrap-style silk-twill midi dress, with a coordinating belt, highlighted her tiny waist. It also has a pleated skirt and a white collar with notched lapels.

Lady Gaga exiting her NYC hotel in a retro-style Rodarte polka-dot dressLady Gaga exiting her NYC hotel in a retro-style Rodarte polka-dot dress on July 31, 2021 (Credit: Mega / WENN)

She kept the rest of her look simple, accessorizing with a pair of $350 Agmes “Sandra” earrings, Edward Avedis ring, and Celine cat-eye sunglasses.

Promoting her upcoming album with Tony, Lady Gaga carried her belongings in a white Delvaux Brilliant MM bag with “Love For Sale” printed in all caps on the front.

Lady Gaga accessorizes with Agmes Sandra earrings, Edward Avedis ring, and Celine cat-eye sunglassesLady Gaga accessorizes with Agmes Sandra earrings, Edward Avedis ring, and Celine cat-eye sunglasses (Credit: Mega / WENN)

To complete the retro look, Lady Gaga slipped her feet into a pair of Giuseppe Zanotti “Raquel” pumps.

Lady Gaga pairs her retro dress with white Giuseppe Zanotti Raquel pumpsLady Gaga pairs her retro dress with white Giuseppe Zanotti Raquel pumps (Credit: Mega / WENN)

Her shoes are classic in white leather with pointed toes and 4-inch chrome heels.

The Giuseppe Zanotti Raquel is a classic pointed-toe pump with Chrome high heelsThe Giuseppe Zanotti Raquel is a classic pointed-toe pump with Chrome high heels

Mod Throwback: Gaga Rocks ‘60s Mini Dress

Just a day earlier, Lady Gaga was pictured in another retro outfit.

Leaving her NYC hotel, the Bad Romance songstress channeled the 1960s in a black Andrew GN Spring 2021 mini dress that features a white embroidered collar, large embellished decorative buttons, and structured squared shoulders with short sleeves.

The dress also has a short, straight hem cut several inches above her knees, allowing her to parade her toned pins.

Lady Gaga channels '60s style in Andrew GN mini dress with white embroidered collar and decorative buttons on July 30, 2021Lady Gaga channels ’60s style in Andrew GN mini dress with white embroidered collar and decorative buttons on July 30, 2021 (Credit: Mega / WENN)

Lady Gaga then pulled her tresses up into a chic French twist and added more sparkle to her look with diamond stud earrings and a diamond band.

She hid her eyes behind black cat-eye sunglasses and carried her stuff in a $4,450 black Louis Vuitton “Capucines” mini bag.

Lady Gaga pairs her mini frock with Louis Vuitton Capucines bag and cat eye sunglassesLady Gaga pairs her mini frock with a Louis Vuitton Capucines bag and cat-eye sunglasses (Credit: Mega / WENN)

For her feet, the chart-topping singer finished off her monochrome outfit with the Giuseppe Zanotti “Sphera” slingback satin pumps.

Lady Gaga adds sparkle to her look with Giuseppe Zanotti Sphera pumpsLady Gaga adds sparkle to her look with Giuseppe Zanotti Sphera pumps (Credit: Mega / WENN)

The Sphera has a spherical vintage-style crystal jewel on the side and is finished with pointed toes, slingback straps, and 4-inch heels.

The Sphera pumps have a vintage-style crystal jewel on one side of the slingback strapThe Sphera pumps have a vintage-style crystal jewel on one side of the slingback strap

Glam Noir: Gaga Slays in Black Bodysuit and Sky-High Heels

Last week, Lady Gaga showed a series of stunning black looks while preparing for her concert with Tony Bennett.

Leaving Highline Stages in Manhattan’s Meatpacking District, the Oscar-winning singer-actress turned heads in a high-neck black bodysuit styled with a Deborah Drattell “Violetta” suede belt.

She showcased her legs in a pair of glittery lurex tights from Fogal and wore an oversized black blazer over her shoulders for some coverage.

Lady Gaga flaunts her figure in a black bodysuit with Fogal lurex tights and an oversized blazer on July 28, 2021Lady Gaga flaunts her figure in a black bodysuit with Fogal lurex tights and an oversized blazer on July 28, 2021 (Credit: Mega / WENN)

Wearing natural makeup with a hint of pink lipstick, Lady Gaga shielded her eyes behind her Dita sunglasses and wrapped her tresses in a black Flapper Genoveffa C turban with the long scarf tucked into her belt.

Lady Gaga shows her unique style sense with a Flapper Genoveffa C turbanLady Gaga shows her unique style sense with a Flapper Genoveffa C turban (Credit: Mega / WENN)

The dramatic boots gave the petite 5-foot-1 ¼ (155.6 cm) singer a towering presence, visually elongating her silhouette and commanding attention even from afar.

Lady Gaga completes a daring monochrome look with Pleaser Infinity sky-high platform bootsLady Gaga completes a daring monochrome look with Pleaser Infinity sky-high platform boots (Credit: Mega / WENN)

Known for using extreme footwear to amplify her performance energy and presence, Gaga’s bold heel choices have become a signature part of her larger-than-life persona—quite literally elevating her fashion and stature.

The Infinity boots by Pleaser boast 9-inch towering heels and 5.25-inch platformsThe Infinity boots by Pleaser boast 9-inch towering heels and 5.25-inch platforms

Lanvin and Feathers: Gaga’s Contrasting Take on Minimalism

On Tuesday, Lady Gaga exited Milk Studios in another pair of monstrous heels. Flaunting her enviable figure, the House of Gucci star wore a black ribbed sweater dress, reportedly unreleased from Lanvin’s Fall/Winter 2021 collection.

Lady Gaga leaving Milk Studios in a Lanvin rib-knit sweater body-con dress on July 27, 2021Lady Gaga leaving Milk Studios in a Lanvin rib-knit sweater body-con dress on July 27, 2021 (Credit: Mega / WENN)

Her long-sleeved high-neck bodycon allowed her to display her tanned legs, while the contrasting white feather detail across the back and sleeves added a quirky element to the rather basic form-fitting frock.

Lady Gaga pairs her mini dress with Pleaser Xtreme lace-up platform bootsLady Gaga pairs her mini dress with Pleaser Xtreme lace-up platform boots (Credit: Mega / WENN)

The Born This Way singer again tapped Pleaser for her extremely high “Xtreme 1020” boots in black vinyl. They feature 7-inch heels, 2.75-inch platforms, and a front lace-up closure.

Shorter than the Infinity, the Xtreme boots have 7-inch heels and 2.75-inch platformsShorter than the Infinity, the Xtreme boots have 7-inch heels and 2.75-inch platforms

Allowing her outfit to do the talking, Lady Gaga kept her accessories simple with statement rings from Edward Avedis and a $2,690 hobo bag with a gold sculptural cat handle from Lanvin.

She pulled her hair into a neat updo and hid her eyes behind her Marc Jacobs Icon cat-eye sunglasses.

Lady Gaga teams her feather-detailed mini dress with Marc Jacobs Icon sunglasses and Lanvin hobo bag with sculptural cat handleLady Gaga teams her feather-detailed mini dress with Marc Jacobs Icon sunglasses and a Lanvin hobo bag with a sculptural cat handle (Credit: Mega / WENN)

On Monday, Lady Gaga kicked off her week in a form-fitting Magda Butrym Fall 2021 rib-knit midi dress.

Hugging every inch of her hourglass figure, the bustier-style black dress features a sweetheart neckline with molded cups, a keyhole cutout across the torso, thin spaghetti straps, and a cinched waist.

Lady Gaga leaving the High line Studios in Madga Butrym dress after a photoshoot in NYC on July 26, 2021Lady Gaga leaving the High Line Studios in Madga Butrym dress after a photoshoot in NYC on July 26, 2021 (Credit: Mega / WENN)

She skipped the jewelry and paired her sleek outfit with a $3,590 boxy Mark Cross Rear Window mini leather overnight case and a pair of $550 Dita “Day Tripper” sunglasses.

Beauty-wise, Lady Gaga styled her brunette hair into a twisted bun and wore dewy makeup with pink lip color.

Lady Gaga wears Dita Day Tripper sunglasses and carries a Mark Cross Rear Window mini leather overnight caseLady Gaga wears Dita Day Tripper sunglasses and carries a Mark Cross Rear Window mini leather overnight case (Credit: Mega / WENN)

Never one to shy away from a fashion risk, Taylor Kinney’s ex teetered on a pair of Pleaser Shoes “Infinity” boots with 9-inch towering heels and 5-inch platforms.

Lady Gaga teeters on a pair of Pleaser Infinity boots with monstrous 9-inch heelsLady Gaga teeters on a pair of Pleaser Infinity boots with monstrous 9-inch heels (Credit: Mega / WENN)

Sky-High Style: Lady Gaga’s Most Iconic Platform Moments

Lady Gaga’s bold fashion choices often include towering heels that make a statement. Here are some of her most memorable platform moments:

Lady Gaga’s 10-Inch Heels at the Met Gala

  • Event: Met Gala
  • Outfit: Gaga stunned in a Versace circuit board jacket with shoulder pads and a matching metal bodice.
  • Footwear: She completed the look with 10-inch stiletto heels by Pleaser Shoes, showcasing her fearless approach to fashion.
  • Read more: Lady Gaga Rocks Insane 10-Inch Platform Heels at Met Gala

Lady Gaga’s Pearl-Embellished Platforms at Glamour’s Gala

  • Event: Glamour’s Women of the Year Gala
  • Outfit: Gaga wore a pearl-studded Thom Browne ensemble with matching gloves and a powdered face.
  • Footwear: She donned custom 10-inch pearl platform heels by A-Morir, adding a sculptural effect to her look.
  • See more: Lady Gaga’s 10-Inch Heels at Glamour’s Gala

Lady Gaga’s Givenchy Platforms at ‘A Star Is Born’ Premiere

  • Event: ‘A Star Is Born’ LA Premiere
  • Outfit: Gaga dazzled in a silver Givenchy Haute Couture gown with a dramatic lace cape.
  • Footwear: She paired the gown with chunky-heeled silver peep-toe platforms, embracing maximum shine.
  • Discover more: Lady Gaga Brings Back Her Iconic Platform Heels

These moments highlight Lady Gaga’s fearless approach to fashion, using towering heels to make bold statements on the red carpet and beyond.