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Easy Winter Outfit Ideas for Errands and Dinner (Under $250, Casual with Clean Lines)

For winter days balancing comfort, practicality, and a casual-yet-polished vibe, look for versatile pieces—think sleek sweaters, streamlined trousers, and minimalist dresses. Clean lines and unfussy silhouettes will keep your look crisp for both errands and casual dinners, while midweight knits and soft tailoring add warmth. If you have a preferred color palette or fabric (like merino or cotton), let me know for an even more tailored list!
@lemanm
1
Long Sleeve Knit Dress
A simple knit dress in a straight or A-line cut is cozy, comfortable, and easy to style for errands or a casual dinner. Choose neutral or muted tones to keep the look refined—works well with boots and a chic coat.
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1
Long Sleeve Knit Dress
@lemanm
A simple knit dress in a straight or A-line cut is cozy, comfortable, and easy to style for errands or a casual dinner. Choose neutral or muted tones to keep the look refined—works well with boots and a chic coat.
Tuckernuck Red Long Sleeve Sara Maxi Dress
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Tuckernuck

Red Long Sleeve Sara Maxi Dress

$178

Tuckernuck

MISA Deliz Dress
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MISA

Deliz Dress

$144

$360

Shopbop

Elie Tahari Cashmere Fit & Flare Dress
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Elie Tahari

Cashmere Fit & Flare Dress

$198

$495

Elie Tahari

Elie Tahari Cashmere Long Sleeve Belted Dress
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Elie Tahari

Cashmere Long Sleeve Belted Dress

$198

$495

Elie Tahari

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@styledtherapy
2
Ribbed Crewneck Sweater
A classic ribbed sweater offers warmth and clean lines, and layers effortlessly over shirts or under outerwear. Stick to minimalist solid colors or subtle stripes for versatility.
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2
Ribbed Crewneck Sweater
@styledtherapy
A classic ribbed sweater offers warmth and clean lines, and layers effortlessly over shirts or under outerwear. Stick to minimalist solid colors or subtle stripes for versatility.
Elie Tahari T-Tahari Rib Mesh Sweater
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Elie Tahari

T-Tahari Rib Mesh Sweater

$31

$78

Elie Tahari

Tuckernuck Oat Alden Ribbed Crewneck
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Tuckernuck

Oat Alden Ribbed Crewneck

$98

Tuckernuck

Allude Ribbed cashmere sweater
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Allude

Ribbed cashmere sweater

$126

$420

Net-a-Porter

LE BOP Noelle Ribbed Sweater
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LE BOP

Noelle Ribbed Sweater

$38.4

$128

Shopbop

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@s.u.a.m.a.r
3
Pleated Wide-Leg Pants
These pants offer a tailored look without feeling too formal. The pleats and wide leg balance comfort with sharp structure—an easy upgrade from jeans for both errands and a casual dinner.
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3
Pleated Wide-Leg Pants
@s.u.a.m.a.r
These pants offer a tailored look without feeling too formal. The pleats and wide leg balance comfort with sharp structure—an easy upgrade from jeans for both errands and a casual dinner.
Pixie Market White Draped Trousers
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Pixie Market

White Draped Trousers

$124

Pixie Market

Pixie Market Tan Wide Leg Pants
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Pixie Market

Tan Wide Leg Pants

$129

Pixie Market

Pixie Market Mel Pleated Tan Pants-BESTSELLER
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Pixie Market

Mel Pleated Tan Pants-BESTSELLER

$76

$142

Pixie Market

moco Metal Waistband Suit Pants
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moco

Metal Waistband Suit Pants

$129

$170

moco

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@minnieyorker
4
Cropped Knit Cardigan
Micro cardigans are a trending staple and deliver a neat, streamlined finish. Button it up as a top for a contemporary, effortless outfit that reads chic and pulled together.
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4
Cropped Knit Cardigan
@minnieyorker
Micro cardigans are a trending staple and deliver a neat, streamlined finish. Button it up as a top for a contemporary, effortless outfit that reads chic and pulled together.
moco Cropped V-neck Knit Cardigan
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moco

Cropped V-neck Knit Cardigan

$175

$195

moco

moco Cropped Raw Hem Cardigan
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moco

Cropped Raw Hem Cardigan

$159

$265

moco

Elie Tahari Two Button Wool Sweater
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Elie Tahari

Two Button Wool Sweater

$230

$328

Elie Tahari

Lioness Head In The Clouds Cardigan
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Lioness

Head In The Clouds Cardigan

$69

Shopbop

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@jordannasharp
5
Straight-Leg Denim with Minimal Detailing
Clean, straight-leg jeans in a dark or classic wash are a wardrobe essential. Minimal hardware and simple lines ensure the outfit remains polished yet casual.
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5
Straight-Leg Denim with Minimal Detailing
@jordannasharp
Clean, straight-leg jeans in a dark or classic wash are a wardrobe essential. Minimal hardware and simple lines ensure the outfit remains polished yet casual.
Citizens Of Humanity Zurie Straight Jeans
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Citizens Of Humanity

Zurie Straight Jeans

$238

Shopbop

Source Unknown Full-Length Straight Jeans, Light Blue
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Source Unknown

Full-Length Straight Jeans, Light Blue

$135

Source Unknown

FRAME The Vertical high-rise straight-leg jeans
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FRAME

The Vertical high-rise straight-leg jeans

$197

$328

Net-a-Porter

moco Seams Detail Straight Jeans
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moco

Seams Detail Straight Jeans

$125

$205

moco

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@alvasperle
6
Soft Jersey Turtleneck Top
A slim-fit turtleneck is a winter staple that feels elevated but relaxed. It's a layering powerhouse—wear solo or under blazers, cardigans, or jackets for an instant outfit upgrade.
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6
Soft Jersey Turtleneck Top
@alvasperle
A slim-fit turtleneck is a winter staple that feels elevated but relaxed. It's a layering powerhouse—wear solo or under blazers, cardigans, or jackets for an instant outfit upgrade.
Ripley Rader Turtleneck
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Ripley Rader

Turtleneck

$128

Shopbop

Elie Tahari Lace Insert Turtleneck Knit
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Elie Tahari

Lace Insert Turtleneck Knit

$67

$168

Elie Tahari

L'AGENCE Lani Turtle Neck Long Sleeve
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L'AGENCE

Lani Turtle Neck Long Sleeve

$140

Shopbop

Elie Tahari Smocked Turtleneck Knit
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Elie Tahari

Smocked Turtleneck Knit

$59

$148

Elie Tahari

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@jeanwang
7
Oversized Blazer
Oversized blazers are trending and instantly sharpen any outfit. Choose one in a midweight material for warmth and a modern, effortless silhouette over tees, sweaters, or even knit dresses.
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7
Oversized Blazer
@jeanwang
Oversized blazers are trending and instantly sharpen any outfit. Choose one in a midweight material for warmth and a modern, effortless silhouette over tees, sweaters, or even knit dresses.
The Frankie Shop Bea oversized cady blazer
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The Frankie Shop

Bea oversized cady blazer

$207

$345

Net-a-Porter

moco Wool Raw Trim Blazer
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moco

Wool Raw Trim Blazer

$229

$380

moco

Pixie Market Oversized Wool-Twill Gold-Button Blazer
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Pixie Market

Oversized Wool-Twill Gold-Button Blazer

$119

$298

Pixie Market

GANNI Oversized twill blazer
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GANNI

Oversized twill blazer

$143

$475

Outnet

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@jellyjelly00
8
Leather Slip-On Loafers
Easy, slip-on loafers finish a casual winter look while keeping it crisp. They pair nicely with wide-leg pants or straight jeans for quick errands or a relaxed dinner.
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8
Leather Slip-On Loafers
@jellyjelly00
Easy, slip-on loafers finish a casual winter look while keeping it crisp. They pair nicely with wide-leg pants or straight jeans for quick errands or a relaxed dinner.
Tony Bianco Gatsby Loafers
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Tony Bianco

Gatsby Loafers

$190

Shopbop

Tory Burch Embellished leather loafers
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Tory Burch

Embellished leather loafers

$210

$300

Net-a-Porter

Tony Bianco Gatsby Loafers
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Tony Bianco

Gatsby Loafers

$190

Shopbop

ALOHAS Aven Loafers
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ALOHAS

Aven Loafers

$190

Shopbop

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@irinstylin
9
Boxy Utility Shirt
Utility shirts are both practical and current; the boxy fit and functional details give a modern, minimal edge that suits casual outings or dinner.
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9
Boxy Utility Shirt
@irinstylin
Utility shirts are both practical and current; the boxy fit and functional details give a modern, minimal edge that suits casual outings or dinner.
Haikure Olive denim shirt
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Haikure

Olive denim shirt

$174

$348

Net-a-Porter

Loulou Studio Moheli twill shirt
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Loulou Studio

Moheli twill shirt

$105

$350

Outnet

XIRENA Adler Shirt
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XIRENA

Adler Shirt

$135

$225

Shopbop

Citizens Of Humanity Claire Origami cotton shirt
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Citizens Of Humanity

Claire Origami cotton shirt

$125

$249

Net-a-Porter

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@elodieromy
10
Modern Boho Blouse
For an easy switch-up, a modern boho blouse with clean embroidery and billowy sleeves adds subtle shape without fuss. It’s comfortable for day-to-night and complements simple denim or tailored pants.
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10
Modern Boho Blouse
@elodieromy
For an easy switch-up, a modern boho blouse with clean embroidery and billowy sleeves adds subtle shape without fuss. It’s comfortable for day-to-night and complements simple denim or tailored pants.
ba&sh Baker Top
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ba&sh

Baker Top

$118

$295

Shopbop

Never Fully Dressed White Love Miley Shirt
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Never Fully Dressed

White Love Miley Shirt

$85

$140

Never Fully Dressed

THE GREAT. The Journey embroidered cotton-gauze top
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THE GREAT.

The Journey embroidered cotton-gauze top

$140

$350

Net-a-Porter

Velvet Maggie cotton gauze blouse
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Velvet

Maggie cotton gauze blouse

$167

$239

Mytheresa

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Velvet Mid-rise cotton canvas wide-leg pants
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Velvet

Mid-rise cotton canvas wide-leg pants

$94

$315

Mytheresa

FRAME Low Slung barrel-leg jeans
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FRAME

Low Slung barrel-leg jeans

$238

$340

Mytheresa

XIRENA Kat Sweatshirt
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XIRENA

Kat Sweatshirt

$248

Shopbop

7 For All Mankind Mid-rise skinny jeans
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7 For All Mankind

Mid-rise skinny jeans

$156

$260

Mytheresa

Alex Mill Britt herringbone cotton jacket
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Alex Mill

Britt herringbone cotton jacket

$113

$225

Outnet

moco Striped Pattern Cotton T-shirt
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moco

Striped Pattern Cotton T-shirt

$89

$110

moco

Nili Lotan Lana striped cotton jersey T-shirt
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Nili Lotan

Lana striped cotton jersey T-shirt

$240

Mytheresa

Velvet Meri stretch-cotton jersey top
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Velvet

Meri stretch-cotton jersey top

$68

$98

Mytheresa

Elie Tahari T-Tahari Stripe Sleeve Sweater
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Elie Tahari

T-Tahari Stripe Sleeve Sweater

$31

$78

Elie Tahari

Alex Mill Jo cotton-poplin shirt
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Alex Mill

Jo cotton-poplin shirt

$73

$145

Outnet

7 For All Mankind Tess high-rise straight jeans
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7 For All Mankind

Tess high-rise straight jeans

$154

$220

Mytheresa

New
New
Alex Mill Paris cotton and cashmere-blend jacket
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Alex Mill

Paris cotton and cashmere-blend jacket

$113

$250

Outnet

Mango Striped boatneck sweatshirt
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Mango

Striped boatneck sweatshirt

$59.99

Mango

Mango Fine-knit boat-neck sweater
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Mango

Fine-knit boat-neck sweater

$49.99

$69.99

Mango

Tuckernuck English Check London Raincoat
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Tuckernuck

English Check London Raincoat

$238

$298

Tuckernuck

Vince Cotton-blend sweater
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Vince

Cotton-blend sweater

$179

$325

Outnet

Mango Fine knit striped jersey
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Mango

Fine knit striped jersey

$49.99

Mango

Veronica Beard Ryleigh cropped high-rise straight-leg jeans
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Veronica Beard

Ryleigh cropped high-rise straight-leg jeans

$149

$298

Outnet

moco Red Striped Cotton T-shirt
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moco

Red Striped Cotton T-shirt

$115

$125

moco

Veronica Beard Ryder high-rise tapered jeans
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Veronica Beard

Ryder high-rise tapered jeans

$126

$278

Outnet

BRAND RECOMMENDATION
HEARTLOOM
Heartloom nails cozy sophistication—think polished knitwear and chic wrap sweaters that layer beautifully for winter. Their easy, refined pieces are perfect for errands but can absolutely transition to dinner, and the brand isn’t yet on everyone’s radar.
View Brand
BRAND RECOMMENDATION
HEARTLOOM
Heartloom nails cozy sophistication—think polished knitwear and chic wrap sweaters that layer beautifully for winter. Their easy, refined pieces are perfect for errands but can absolutely transition to dinner, and the brand isn’t yet on everyone’s radar.
HEARTLOOM Sparrow Cardi
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HEARTLOOM

Sparrow Cardi

$46

$109

Revolve

HEARTLOOM Alix Cardi
save

HEARTLOOM

Alix Cardi

$42

$119

Revolve

HEARTLOOM Beatriz Trench Coat
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HEARTLOOM

Beatriz Trench Coat

$179

Revolve

New
New
HEARTLOOM Jaden Sweater
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HEARTLOOM

Jaden Sweater

$35

$99

Revolve

View brand
FABIANA FILIPPI Houndstooth cotton jacket
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FABIANA FILIPPI

Houndstooth cotton jacket

$156

$1,035

Outnet

FRAME Striped cotton T-shirt
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FRAME

Striped cotton T-shirt

$161

$230

Mytheresa

3.1 Phillip Lim Striped wool cardigan
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3.1 Phillip Lim

Striped wool cardigan

$179

$595

Outnet

FRAME The Jetset high-rise flared jeans
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FRAME

The Jetset high-rise flared jeans

$114

$228

Outnet

moco Belted A-line Pleated Skirt
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moco

Belted A-line Pleated Skirt

$205

$240

moco

7 For All Mankind Logan Cargo cropped straight jeans
save

7 For All Mankind

Logan Cargo cropped straight jeans

$151

$252

Mytheresa

rag & bone Madix ribbed-knit polo sweater
save

rag & bone

Madix ribbed-knit polo sweater

$157

$348

Outnet

FRAME Two-tone wool-blend half-zip sweater
save

FRAME

Two-tone wool-blend half-zip sweater

$227

$648

Outnet

Tuckernuck Navy Gingham Cashel Collarless Quilted Jacket
save

Tuckernuck

Navy Gingham Cashel Collarless Quilted Jacket

$250

Tuckernuck

Agolde Adine cotton jersey T-shirt
save

Agolde

Adine cotton jersey T-shirt

$105

Mytheresa

LESET Rio jersey stirrup leggings
save

LESET

Rio jersey stirrup leggings

$215

Mytheresa

7 For All Mankind Stovepipe Straight mid-rise straight jeans
save

7 For All Mankind

Stovepipe Straight mid-rise straight jeans

$250

Mytheresa

Veronica Beard Hovey striped cotton-jersey top
save

Veronica Beard

Hovey striped cotton-jersey top

$75

$248

Outnet

LESET Margo cotton jersey T-shirt
save

LESET

Margo cotton jersey T-shirt

$85

Mytheresa

FRAME Le High Straight cropped distressed high-rise straight-leg jeans
save

FRAME

Le High Straight cropped distressed high-rise straight-leg jeans

$72

$238

Outnet

Tuckernuck White Long Sleeve Pique Holmes Boyfriend Polo
save

Tuckernuck

White Long Sleeve Pique Holmes Boyfriend Polo

$128

Tuckernuck

3.1 Phillip Lim Striped wool sweater
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3.1 Phillip Lim

Striped wool sweater

$165

$550

Outnet

Alex Mill Anne Quilted Jacket In Nylon
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Alex Mill

Anne Quilted Jacket In Nylon

$225

$375

Shopbop

superdown Sashia Polo Top
save

superdown

Sashia Polo Top

$68

Revolve

Tuckernuck Navy Striped Ella Sweater Blouse
save

Tuckernuck

Navy Striped Ella Sweater Blouse

$168

Tuckernuck

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