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Drew Barrymore is my winter style icon

Photos / @thedrewbarrymoreshow

I have never once watched a full episode of The Drew Barrymore Show, but the screenshots on my phone might suggest otherwise. They're all focused on one thing: Drew’s dreamy vintage inspired outfits.

The morning talk show hosted by the sunny Hollywood star launched during the early days of the pandemic, with Charlie’s Angels co-stars Cameron Diaz and Lucy Liu as the first guests. That set the bar for the access Drew has: she regularly welcomes impressive celebrity guests, who are all clearly delighted to be there (the show’s Instagram grid is a sea of toothy grins).

It’s brought a sort of manic, surrealist energy to the idea of a traditional morning show, and it feels very now. The set - including that for the Drew’s News segment - looks like it’s from Anchorman, and Drag Race judge Ross Matthews is her co-host. I think The Cut explained it best when they wrote that “it is the only television show that represents how I feel inside my head in 2020: inescapably chaotic and just trying to hang in there”.

That energy is still through the roof, with Drew’s signature enthusiasm matched only by her empathy. She’s had Scarlett Johansen talking about her personal life, Gwyneth Paltrow coming up with new, ‘safe-for-television’ words for vagina (“lady bits”), and bonded with Paris Hilton over playing together as kids, and their shared experience at being placed in solitary confinement as ‘troubled’ teens.

She giddily met SNL’s Chloe Fineman - known to many on Instagram as @chloeiscrazy - and asked Chloe to do her genius Drew Barrymore impersonation to her face. She featured Billy Porter in a segment called ‘Sing to a Flower’ which was exactly what it says on the tin: Billy, singing to an oversized fake flower.

Because she’s Drew, she also loves to indulge in some nostalgia, having revisited her Josie “Grossie” character, complete with pink prom dress and braces, and earlier this week reminiscing with her E.T co-star Dee Wallace. In another much-hyped chat and throwback to that weird time in the 2000s when they were married (!?), she reunited with her ex-husband Tom Green.

Photos / @thedrewbarrymoreshow

There’s plenty of star power, both A and D list, but the show - which Drew describes as ‘optimism TV’ - also features everything from stain removal to cooking tutorials to money advice. Basically, all of the things you’d expect on a morning show, just hosted by one of Hollywood’s biggest stars.

But the part that I’m most interested in is Drew’s Dressing Room. That’s the show's name for her talk show wardrobe, which is vintage influenced and not particularly groundbreaking, but exactly how I want to dress for winter. Think boho but buttoned up, a contradiction to Drew’s flower child persona. 

(Sidenote: Drew has always been a bit of an underrated style icon, from her messy ‘90s grunge party girl phase to the sunflowers and butterflies era. That photo of Drew turning up to the premiere of Charlie’s Angels 2 with Cameron Diaz, wearing cropped leather pants and a cropped T-shirt with the slogan ‘my boyfriend is out of town’ while holding an open bottle of Dom Perignon? Today’s Gen-Z does Y2K girlies could never.)

Drew’s Dressing Room features a regular autumnal palette - brown, ochre, mustard, maroon, more brown - and plenty of tweed and pussybow blouses. Plus, a very specific style of knee-high boot that she has in various colours. No look is complete without these specially made remakes of a Jimmy Choo pair Drew had from 2016 - suede, platformed, with a skinny heel.

Drew will often wear them with pieces from brands known for their contemporary take on vintage, like Saint Laurent, Gucci, Tory Burch, Gabriela Hearst, Chloe, Michael Kors and Diane von Furstenberg.

Apparently her stylist Lee Harris was partly inspired by a third grade art teacher (‘art teacher chic’ or ‘librarian chic’ - in the same family tree as Prada’s ‘ugly chic’ - have always been the epitome of cool to me), as well as the obvious 1970s icons, like Annie Hall, Bianca Jagger, and early Charlie’s Angels Shelley Hack and Jacylyn Smith.

The best thing is that this new Drew outfit formula is very easy, and great inspiration for those who don’t have time or inclination to put too much thought into their winter ensembles. You take a blouse - printed and/or with a pussybow - and add a midi-skirt, then add some knee-high boots. If you have time, add a vest or waistcoat, maybe a flower corsage, definitely a belt. They’re all pieces you’ll likely have in your wardrobe already, or are easily found at a vintage store. Lots of local designers have done their take on many of these pieces for winter too.

Sometimes Drew will mix it up in a flowing printed dress, loose-fit high-waisted pants or culottes (I'm not the biggest fan of those...), but the ethos is still the same: effortless, groovy and vintage inspired. But always, always with knee-high boots. 

SHOP THE DREW OUTFIT FORMULA:

BLOUSE

+ VEST

+ MIDI SKIRT

+ KNEE-HIGH BOOTS

= GROOVY DREW VIBES

No items found.
Photos / @thedrewbarrymoreshow

I have never once watched a full episode of The Drew Barrymore Show, but the screenshots on my phone might suggest otherwise. They're all focused on one thing: Drew’s dreamy vintage inspired outfits.

The morning talk show hosted by the sunny Hollywood star launched during the early days of the pandemic, with Charlie’s Angels co-stars Cameron Diaz and Lucy Liu as the first guests. That set the bar for the access Drew has: she regularly welcomes impressive celebrity guests, who are all clearly delighted to be there (the show’s Instagram grid is a sea of toothy grins).

It’s brought a sort of manic, surrealist energy to the idea of a traditional morning show, and it feels very now. The set - including that for the Drew’s News segment - looks like it’s from Anchorman, and Drag Race judge Ross Matthews is her co-host. I think The Cut explained it best when they wrote that “it is the only television show that represents how I feel inside my head in 2020: inescapably chaotic and just trying to hang in there”.

That energy is still through the roof, with Drew’s signature enthusiasm matched only by her empathy. She’s had Scarlett Johansen talking about her personal life, Gwyneth Paltrow coming up with new, ‘safe-for-television’ words for vagina (“lady bits”), and bonded with Paris Hilton over playing together as kids, and their shared experience at being placed in solitary confinement as ‘troubled’ teens.

She giddily met SNL’s Chloe Fineman - known to many on Instagram as @chloeiscrazy - and asked Chloe to do her genius Drew Barrymore impersonation to her face. She featured Billy Porter in a segment called ‘Sing to a Flower’ which was exactly what it says on the tin: Billy, singing to an oversized fake flower.

Because she’s Drew, she also loves to indulge in some nostalgia, having revisited her Josie “Grossie” character, complete with pink prom dress and braces, and earlier this week reminiscing with her E.T co-star Dee Wallace. In another much-hyped chat and throwback to that weird time in the 2000s when they were married (!?), she reunited with her ex-husband Tom Green.

Photos / @thedrewbarrymoreshow

There’s plenty of star power, both A and D list, but the show - which Drew describes as ‘optimism TV’ - also features everything from stain removal to cooking tutorials to money advice. Basically, all of the things you’d expect on a morning show, just hosted by one of Hollywood’s biggest stars.

But the part that I’m most interested in is Drew’s Dressing Room. That’s the show's name for her talk show wardrobe, which is vintage influenced and not particularly groundbreaking, but exactly how I want to dress for winter. Think boho but buttoned up, a contradiction to Drew’s flower child persona. 

(Sidenote: Drew has always been a bit of an underrated style icon, from her messy ‘90s grunge party girl phase to the sunflowers and butterflies era. That photo of Drew turning up to the premiere of Charlie’s Angels 2 with Cameron Diaz, wearing cropped leather pants and a cropped T-shirt with the slogan ‘my boyfriend is out of town’ while holding an open bottle of Dom Perignon? Today’s Gen-Z does Y2K girlies could never.)

Drew’s Dressing Room features a regular autumnal palette - brown, ochre, mustard, maroon, more brown - and plenty of tweed and pussybow blouses. Plus, a very specific style of knee-high boot that she has in various colours. No look is complete without these specially made remakes of a Jimmy Choo pair Drew had from 2016 - suede, platformed, with a skinny heel.

Drew will often wear them with pieces from brands known for their contemporary take on vintage, like Saint Laurent, Gucci, Tory Burch, Gabriela Hearst, Chloe, Michael Kors and Diane von Furstenberg.

Apparently her stylist Lee Harris was partly inspired by a third grade art teacher (‘art teacher chic’ or ‘librarian chic’ - in the same family tree as Prada’s ‘ugly chic’ - have always been the epitome of cool to me), as well as the obvious 1970s icons, like Annie Hall, Bianca Jagger, and early Charlie’s Angels Shelley Hack and Jacylyn Smith.

The best thing is that this new Drew outfit formula is very easy, and great inspiration for those who don’t have time or inclination to put too much thought into their winter ensembles. You take a blouse - printed and/or with a pussybow - and add a midi-skirt, then add some knee-high boots. If you have time, add a vest or waistcoat, maybe a flower corsage, definitely a belt. They’re all pieces you’ll likely have in your wardrobe already, or are easily found at a vintage store. Lots of local designers have done their take on many of these pieces for winter too.

Sometimes Drew will mix it up in a flowing printed dress, loose-fit high-waisted pants or culottes (I'm not the biggest fan of those...), but the ethos is still the same: effortless, groovy and vintage inspired. But always, always with knee-high boots. 

SHOP THE DREW OUTFIT FORMULA:

BLOUSE

+ VEST

+ MIDI SKIRT

+ KNEE-HIGH BOOTS

= GROOVY DREW VIBES

Creativity, evocative visual storytelling and good journalism come at a price. Support our work and join the Ensemble membership program
No items found.

Drew Barrymore is my winter style icon

Photos / @thedrewbarrymoreshow

I have never once watched a full episode of The Drew Barrymore Show, but the screenshots on my phone might suggest otherwise. They're all focused on one thing: Drew’s dreamy vintage inspired outfits.

The morning talk show hosted by the sunny Hollywood star launched during the early days of the pandemic, with Charlie’s Angels co-stars Cameron Diaz and Lucy Liu as the first guests. That set the bar for the access Drew has: she regularly welcomes impressive celebrity guests, who are all clearly delighted to be there (the show’s Instagram grid is a sea of toothy grins).

It’s brought a sort of manic, surrealist energy to the idea of a traditional morning show, and it feels very now. The set - including that for the Drew’s News segment - looks like it’s from Anchorman, and Drag Race judge Ross Matthews is her co-host. I think The Cut explained it best when they wrote that “it is the only television show that represents how I feel inside my head in 2020: inescapably chaotic and just trying to hang in there”.

That energy is still through the roof, with Drew’s signature enthusiasm matched only by her empathy. She’s had Scarlett Johansen talking about her personal life, Gwyneth Paltrow coming up with new, ‘safe-for-television’ words for vagina (“lady bits”), and bonded with Paris Hilton over playing together as kids, and their shared experience at being placed in solitary confinement as ‘troubled’ teens.

She giddily met SNL’s Chloe Fineman - known to many on Instagram as @chloeiscrazy - and asked Chloe to do her genius Drew Barrymore impersonation to her face. She featured Billy Porter in a segment called ‘Sing to a Flower’ which was exactly what it says on the tin: Billy, singing to an oversized fake flower.

Because she’s Drew, she also loves to indulge in some nostalgia, having revisited her Josie “Grossie” character, complete with pink prom dress and braces, and earlier this week reminiscing with her E.T co-star Dee Wallace. In another much-hyped chat and throwback to that weird time in the 2000s when they were married (!?), she reunited with her ex-husband Tom Green.

Photos / @thedrewbarrymoreshow

There’s plenty of star power, both A and D list, but the show - which Drew describes as ‘optimism TV’ - also features everything from stain removal to cooking tutorials to money advice. Basically, all of the things you’d expect on a morning show, just hosted by one of Hollywood’s biggest stars.

But the part that I’m most interested in is Drew’s Dressing Room. That’s the show's name for her talk show wardrobe, which is vintage influenced and not particularly groundbreaking, but exactly how I want to dress for winter. Think boho but buttoned up, a contradiction to Drew’s flower child persona. 

(Sidenote: Drew has always been a bit of an underrated style icon, from her messy ‘90s grunge party girl phase to the sunflowers and butterflies era. That photo of Drew turning up to the premiere of Charlie’s Angels 2 with Cameron Diaz, wearing cropped leather pants and a cropped T-shirt with the slogan ‘my boyfriend is out of town’ while holding an open bottle of Dom Perignon? Today’s Gen-Z does Y2K girlies could never.)

Drew’s Dressing Room features a regular autumnal palette - brown, ochre, mustard, maroon, more brown - and plenty of tweed and pussybow blouses. Plus, a very specific style of knee-high boot that she has in various colours. No look is complete without these specially made remakes of a Jimmy Choo pair Drew had from 2016 - suede, platformed, with a skinny heel.

Drew will often wear them with pieces from brands known for their contemporary take on vintage, like Saint Laurent, Gucci, Tory Burch, Gabriela Hearst, Chloe, Michael Kors and Diane von Furstenberg.

Apparently her stylist Lee Harris was partly inspired by a third grade art teacher (‘art teacher chic’ or ‘librarian chic’ - in the same family tree as Prada’s ‘ugly chic’ - have always been the epitome of cool to me), as well as the obvious 1970s icons, like Annie Hall, Bianca Jagger, and early Charlie’s Angels Shelley Hack and Jacylyn Smith.

The best thing is that this new Drew outfit formula is very easy, and great inspiration for those who don’t have time or inclination to put too much thought into their winter ensembles. You take a blouse - printed and/or with a pussybow - and add a midi-skirt, then add some knee-high boots. If you have time, add a vest or waistcoat, maybe a flower corsage, definitely a belt. They’re all pieces you’ll likely have in your wardrobe already, or are easily found at a vintage store. Lots of local designers have done their take on many of these pieces for winter too.

Sometimes Drew will mix it up in a flowing printed dress, loose-fit high-waisted pants or culottes (I'm not the biggest fan of those...), but the ethos is still the same: effortless, groovy and vintage inspired. But always, always with knee-high boots. 

SHOP THE DREW OUTFIT FORMULA:

BLOUSE

+ VEST

+ MIDI SKIRT

+ KNEE-HIGH BOOTS

= GROOVY DREW VIBES

No items found.
Creativity, evocative visual storytelling and good journalism come at a price. Support our work and join the Ensemble membership program

Drew Barrymore is my winter style icon

Photos / @thedrewbarrymoreshow

I have never once watched a full episode of The Drew Barrymore Show, but the screenshots on my phone might suggest otherwise. They're all focused on one thing: Drew’s dreamy vintage inspired outfits.

The morning talk show hosted by the sunny Hollywood star launched during the early days of the pandemic, with Charlie’s Angels co-stars Cameron Diaz and Lucy Liu as the first guests. That set the bar for the access Drew has: she regularly welcomes impressive celebrity guests, who are all clearly delighted to be there (the show’s Instagram grid is a sea of toothy grins).

It’s brought a sort of manic, surrealist energy to the idea of a traditional morning show, and it feels very now. The set - including that for the Drew’s News segment - looks like it’s from Anchorman, and Drag Race judge Ross Matthews is her co-host. I think The Cut explained it best when they wrote that “it is the only television show that represents how I feel inside my head in 2020: inescapably chaotic and just trying to hang in there”.

That energy is still through the roof, with Drew’s signature enthusiasm matched only by her empathy. She’s had Scarlett Johansen talking about her personal life, Gwyneth Paltrow coming up with new, ‘safe-for-television’ words for vagina (“lady bits”), and bonded with Paris Hilton over playing together as kids, and their shared experience at being placed in solitary confinement as ‘troubled’ teens.

She giddily met SNL’s Chloe Fineman - known to many on Instagram as @chloeiscrazy - and asked Chloe to do her genius Drew Barrymore impersonation to her face. She featured Billy Porter in a segment called ‘Sing to a Flower’ which was exactly what it says on the tin: Billy, singing to an oversized fake flower.

Because she’s Drew, she also loves to indulge in some nostalgia, having revisited her Josie “Grossie” character, complete with pink prom dress and braces, and earlier this week reminiscing with her E.T co-star Dee Wallace. In another much-hyped chat and throwback to that weird time in the 2000s when they were married (!?), she reunited with her ex-husband Tom Green.

Photos / @thedrewbarrymoreshow

There’s plenty of star power, both A and D list, but the show - which Drew describes as ‘optimism TV’ - also features everything from stain removal to cooking tutorials to money advice. Basically, all of the things you’d expect on a morning show, just hosted by one of Hollywood’s biggest stars.

But the part that I’m most interested in is Drew’s Dressing Room. That’s the show's name for her talk show wardrobe, which is vintage influenced and not particularly groundbreaking, but exactly how I want to dress for winter. Think boho but buttoned up, a contradiction to Drew’s flower child persona. 

(Sidenote: Drew has always been a bit of an underrated style icon, from her messy ‘90s grunge party girl phase to the sunflowers and butterflies era. That photo of Drew turning up to the premiere of Charlie’s Angels 2 with Cameron Diaz, wearing cropped leather pants and a cropped T-shirt with the slogan ‘my boyfriend is out of town’ while holding an open bottle of Dom Perignon? Today’s Gen-Z does Y2K girlies could never.)

Drew’s Dressing Room features a regular autumnal palette - brown, ochre, mustard, maroon, more brown - and plenty of tweed and pussybow blouses. Plus, a very specific style of knee-high boot that she has in various colours. No look is complete without these specially made remakes of a Jimmy Choo pair Drew had from 2016 - suede, platformed, with a skinny heel.

Drew will often wear them with pieces from brands known for their contemporary take on vintage, like Saint Laurent, Gucci, Tory Burch, Gabriela Hearst, Chloe, Michael Kors and Diane von Furstenberg.

Apparently her stylist Lee Harris was partly inspired by a third grade art teacher (‘art teacher chic’ or ‘librarian chic’ - in the same family tree as Prada’s ‘ugly chic’ - have always been the epitome of cool to me), as well as the obvious 1970s icons, like Annie Hall, Bianca Jagger, and early Charlie’s Angels Shelley Hack and Jacylyn Smith.

The best thing is that this new Drew outfit formula is very easy, and great inspiration for those who don’t have time or inclination to put too much thought into their winter ensembles. You take a blouse - printed and/or with a pussybow - and add a midi-skirt, then add some knee-high boots. If you have time, add a vest or waistcoat, maybe a flower corsage, definitely a belt. They’re all pieces you’ll likely have in your wardrobe already, or are easily found at a vintage store. Lots of local designers have done their take on many of these pieces for winter too.

Sometimes Drew will mix it up in a flowing printed dress, loose-fit high-waisted pants or culottes (I'm not the biggest fan of those...), but the ethos is still the same: effortless, groovy and vintage inspired. But always, always with knee-high boots. 

SHOP THE DREW OUTFIT FORMULA:

BLOUSE

+ VEST

+ MIDI SKIRT

+ KNEE-HIGH BOOTS

= GROOVY DREW VIBES

Creativity, evocative visual storytelling and good journalism come at a price. Support our work and join the Ensemble membership program
No items found.
Photos / @thedrewbarrymoreshow

I have never once watched a full episode of The Drew Barrymore Show, but the screenshots on my phone might suggest otherwise. They're all focused on one thing: Drew’s dreamy vintage inspired outfits.

The morning talk show hosted by the sunny Hollywood star launched during the early days of the pandemic, with Charlie’s Angels co-stars Cameron Diaz and Lucy Liu as the first guests. That set the bar for the access Drew has: she regularly welcomes impressive celebrity guests, who are all clearly delighted to be there (the show’s Instagram grid is a sea of toothy grins).

It’s brought a sort of manic, surrealist energy to the idea of a traditional morning show, and it feels very now. The set - including that for the Drew’s News segment - looks like it’s from Anchorman, and Drag Race judge Ross Matthews is her co-host. I think The Cut explained it best when they wrote that “it is the only television show that represents how I feel inside my head in 2020: inescapably chaotic and just trying to hang in there”.

That energy is still through the roof, with Drew’s signature enthusiasm matched only by her empathy. She’s had Scarlett Johansen talking about her personal life, Gwyneth Paltrow coming up with new, ‘safe-for-television’ words for vagina (“lady bits”), and bonded with Paris Hilton over playing together as kids, and their shared experience at being placed in solitary confinement as ‘troubled’ teens.

She giddily met SNL’s Chloe Fineman - known to many on Instagram as @chloeiscrazy - and asked Chloe to do her genius Drew Barrymore impersonation to her face. She featured Billy Porter in a segment called ‘Sing to a Flower’ which was exactly what it says on the tin: Billy, singing to an oversized fake flower.

Because she’s Drew, she also loves to indulge in some nostalgia, having revisited her Josie “Grossie” character, complete with pink prom dress and braces, and earlier this week reminiscing with her E.T co-star Dee Wallace. In another much-hyped chat and throwback to that weird time in the 2000s when they were married (!?), she reunited with her ex-husband Tom Green.

Photos / @thedrewbarrymoreshow

There’s plenty of star power, both A and D list, but the show - which Drew describes as ‘optimism TV’ - also features everything from stain removal to cooking tutorials to money advice. Basically, all of the things you’d expect on a morning show, just hosted by one of Hollywood’s biggest stars.

But the part that I’m most interested in is Drew’s Dressing Room. That’s the show's name for her talk show wardrobe, which is vintage influenced and not particularly groundbreaking, but exactly how I want to dress for winter. Think boho but buttoned up, a contradiction to Drew’s flower child persona. 

(Sidenote: Drew has always been a bit of an underrated style icon, from her messy ‘90s grunge party girl phase to the sunflowers and butterflies era. That photo of Drew turning up to the premiere of Charlie’s Angels 2 with Cameron Diaz, wearing cropped leather pants and a cropped T-shirt with the slogan ‘my boyfriend is out of town’ while holding an open bottle of Dom Perignon? Today’s Gen-Z does Y2K girlies could never.)

Drew’s Dressing Room features a regular autumnal palette - brown, ochre, mustard, maroon, more brown - and plenty of tweed and pussybow blouses. Plus, a very specific style of knee-high boot that she has in various colours. No look is complete without these specially made remakes of a Jimmy Choo pair Drew had from 2016 - suede, platformed, with a skinny heel.

Drew will often wear them with pieces from brands known for their contemporary take on vintage, like Saint Laurent, Gucci, Tory Burch, Gabriela Hearst, Chloe, Michael Kors and Diane von Furstenberg.

Apparently her stylist Lee Harris was partly inspired by a third grade art teacher (‘art teacher chic’ or ‘librarian chic’ - in the same family tree as Prada’s ‘ugly chic’ - have always been the epitome of cool to me), as well as the obvious 1970s icons, like Annie Hall, Bianca Jagger, and early Charlie’s Angels Shelley Hack and Jacylyn Smith.

The best thing is that this new Drew outfit formula is very easy, and great inspiration for those who don’t have time or inclination to put too much thought into their winter ensembles. You take a blouse - printed and/or with a pussybow - and add a midi-skirt, then add some knee-high boots. If you have time, add a vest or waistcoat, maybe a flower corsage, definitely a belt. They’re all pieces you’ll likely have in your wardrobe already, or are easily found at a vintage store. Lots of local designers have done their take on many of these pieces for winter too.

Sometimes Drew will mix it up in a flowing printed dress, loose-fit high-waisted pants or culottes (I'm not the biggest fan of those...), but the ethos is still the same: effortless, groovy and vintage inspired. But always, always with knee-high boots. 

SHOP THE DREW OUTFIT FORMULA:

BLOUSE

+ VEST

+ MIDI SKIRT

+ KNEE-HIGH BOOTS

= GROOVY DREW VIBES

No items found.
Creativity, evocative visual storytelling and good journalism come at a price. Support our work and join the Ensemble membership program

Drew Barrymore is my winter style icon

Photos / @thedrewbarrymoreshow

I have never once watched a full episode of The Drew Barrymore Show, but the screenshots on my phone might suggest otherwise. They're all focused on one thing: Drew’s dreamy vintage inspired outfits.

The morning talk show hosted by the sunny Hollywood star launched during the early days of the pandemic, with Charlie’s Angels co-stars Cameron Diaz and Lucy Liu as the first guests. That set the bar for the access Drew has: she regularly welcomes impressive celebrity guests, who are all clearly delighted to be there (the show’s Instagram grid is a sea of toothy grins).

It’s brought a sort of manic, surrealist energy to the idea of a traditional morning show, and it feels very now. The set - including that for the Drew’s News segment - looks like it’s from Anchorman, and Drag Race judge Ross Matthews is her co-host. I think The Cut explained it best when they wrote that “it is the only television show that represents how I feel inside my head in 2020: inescapably chaotic and just trying to hang in there”.

That energy is still through the roof, with Drew’s signature enthusiasm matched only by her empathy. She’s had Scarlett Johansen talking about her personal life, Gwyneth Paltrow coming up with new, ‘safe-for-television’ words for vagina (“lady bits”), and bonded with Paris Hilton over playing together as kids, and their shared experience at being placed in solitary confinement as ‘troubled’ teens.

She giddily met SNL’s Chloe Fineman - known to many on Instagram as @chloeiscrazy - and asked Chloe to do her genius Drew Barrymore impersonation to her face. She featured Billy Porter in a segment called ‘Sing to a Flower’ which was exactly what it says on the tin: Billy, singing to an oversized fake flower.

Because she’s Drew, she also loves to indulge in some nostalgia, having revisited her Josie “Grossie” character, complete with pink prom dress and braces, and earlier this week reminiscing with her E.T co-star Dee Wallace. In another much-hyped chat and throwback to that weird time in the 2000s when they were married (!?), she reunited with her ex-husband Tom Green.

Photos / @thedrewbarrymoreshow

There’s plenty of star power, both A and D list, but the show - which Drew describes as ‘optimism TV’ - also features everything from stain removal to cooking tutorials to money advice. Basically, all of the things you’d expect on a morning show, just hosted by one of Hollywood’s biggest stars.

But the part that I’m most interested in is Drew’s Dressing Room. That’s the show's name for her talk show wardrobe, which is vintage influenced and not particularly groundbreaking, but exactly how I want to dress for winter. Think boho but buttoned up, a contradiction to Drew’s flower child persona. 

(Sidenote: Drew has always been a bit of an underrated style icon, from her messy ‘90s grunge party girl phase to the sunflowers and butterflies era. That photo of Drew turning up to the premiere of Charlie’s Angels 2 with Cameron Diaz, wearing cropped leather pants and a cropped T-shirt with the slogan ‘my boyfriend is out of town’ while holding an open bottle of Dom Perignon? Today’s Gen-Z does Y2K girlies could never.)

Drew’s Dressing Room features a regular autumnal palette - brown, ochre, mustard, maroon, more brown - and plenty of tweed and pussybow blouses. Plus, a very specific style of knee-high boot that she has in various colours. No look is complete without these specially made remakes of a Jimmy Choo pair Drew had from 2016 - suede, platformed, with a skinny heel.

Drew will often wear them with pieces from brands known for their contemporary take on vintage, like Saint Laurent, Gucci, Tory Burch, Gabriela Hearst, Chloe, Michael Kors and Diane von Furstenberg.

Apparently her stylist Lee Harris was partly inspired by a third grade art teacher (‘art teacher chic’ or ‘librarian chic’ - in the same family tree as Prada’s ‘ugly chic’ - have always been the epitome of cool to me), as well as the obvious 1970s icons, like Annie Hall, Bianca Jagger, and early Charlie’s Angels Shelley Hack and Jacylyn Smith.

The best thing is that this new Drew outfit formula is very easy, and great inspiration for those who don’t have time or inclination to put too much thought into their winter ensembles. You take a blouse - printed and/or with a pussybow - and add a midi-skirt, then add some knee-high boots. If you have time, add a vest or waistcoat, maybe a flower corsage, definitely a belt. They’re all pieces you’ll likely have in your wardrobe already, or are easily found at a vintage store. Lots of local designers have done their take on many of these pieces for winter too.

Sometimes Drew will mix it up in a flowing printed dress, loose-fit high-waisted pants or culottes (I'm not the biggest fan of those...), but the ethos is still the same: effortless, groovy and vintage inspired. But always, always with knee-high boots. 

SHOP THE DREW OUTFIT FORMULA:

BLOUSE

+ VEST

+ MIDI SKIRT

+ KNEE-HIGH BOOTS

= GROOVY DREW VIBES

Creativity, evocative visual storytelling and good journalism come at a price. Support our work and join the Ensemble membership program
No items found.