Challenge Accepted: I Created 5 Elegant Winter Outfits From Madewell and J.Crew for Under $452

I’m not sure if many people know this, but one of my favorite pastimes is curating my ideal outfits from various brands and retailers. It’s a thrilling yet dangerously tempting hobby; I often purchase far more than I intend to. If you’re on a budget or participating in a no-spend challenge this January, you might want to steer clear of this activity.

Recently, as I was piecing together looks from both J.Crew and Madewell, I decided to take on a fun challenge: creating five stylish winter outfits that wouldn’t break the bank.

What follows are carefully selected outfits that cater to various occasions this winter. Whether you’re seeking a chic ensemble for a cozy weekend getaway, a romantic date night with someone special, or perhaps a fresh take on your workwear, I’ve got you covered. With an array of cozy sweaters, sophisticated wool coats, and timeless boots, each outfit exudes elevated style for the chilly season. The cherry on top? None of the curated looks exceeds $452.

Outfit #1

(Image credit: J.Crew, Madewell)

When I saw this sweater with the attached scarf, I knew I had to create an outfit around it. Initially, I considered pairing it with blue straight-leg jeans. However, I found the perfect pair of wide-leg trousers in a complementary shade. I added J.Crew’s best-selling brown suede bucket bagand supple chocolate-brown loafers to maintain a monochrome look. This outfit is perfect for the office or a weekend brunch with friends.

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j.crew

Pullover Sweater With Scarf

Madewell, The Harlow Superwide-Leg Trouser in Brushed Twill

Madewell

The Harlow Superwide-Leg Trouser in Brushed Twill

Madewell, The Grayson Penny Loafer

Madewell

The Grayson Penny Loafer

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j.crew

Berkeley Bucket Bag in Leather and Suede

Outfit #2

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(Image credit: J.Crew; Madewell)

Looking to create an expensive-looking outfit without breaking the bank? Here’s a pro tip: The classic combination of black and white can instantly elevate your look. That’s why I decided to curate a chic black-and-white ensemble featuring pieces from J.Crew and Madewell. I started with a versatile white button-down shirt—an absolute wardrobe essential—and white jeans. But let’s be honest. Accessories are the key to making this outfit shine. I selected Madewell’s Western-inspired belt, paired it with the brand’s timeless ankle boots, and topped it off with a chic chain-link necklace from J.Crew to tie in the gold. This outfit exudes sophistication and elegance while staying budget-friendly.

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j.crew

Garçon Classic Shirt in Cotton Poplin

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j.crew

High-Rise Straight Jean in 1996 Semi-Stretch

Madewell, Triple Metal Keeper Belt

Madewell

Triple Metal Keeper Belt

Madewell, The Dimes Stiletto-Heel Ankle Boot

Madewell

The Dimes Stiletto-Heel Ankle Boot

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j.crew

Metallic Chainlink Necklace

Outfit #3

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(Image credit: J.Crew; Madewell)

After hearing Eliza Huber, senior editor at Who What Wear, enthusiastically praise J.Crew’s Cashmere Shrunken Crewneck Sweater, I was convinced it deserved a place in this shopping guide. She frequently emphasizes its remarkable comfort and how it perfectly hits below the belly button, creating a flattering silhouette. Eliza also suggests opting for a size up and washing it to achieve an ideal fit that feels tailor-made. This versatile piece is elegant when paired with a flowing maxi skirt, yet it seamlessly transitions to a more casual vibe with baggy or straight-leg jeans and stylish boots, showcasing its true adaptability for any occasion.

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j.crew

Cashmere Shrunken Crewneck Sweater

madewell, The '90s Straight Jeans

madewell

The ’90s Straight Jeans

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j.crew

New Stevie Ankle Boots in Leather

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j.crew

Metallic Ball Earrings

Outfit #4

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(Image credit: J.Crew, Madewell)

If you’re searching for a winter dress for a bridal shower, date night, or cocktail party, end your search with exquisite offerings from J.Crew and Madewell. One standout piece is Madewell’s Merino Wool Sweater Maxi Dress, which envelops you in luxurious comfort reminiscent of a cozy blanket. Its A-line silhouette not only flatters various body shapes but also adds a touch of sophistication to your look. While the dress pairs nicely with socks and loafers, it looks the most stylish with pointed-toe knee-high leather boots that peek out from the hem. Complete the outfit with J.Crew’s Bordeaux Bag, which looks three times its price.

MW, Merino Wool Sweater Maxi Dress

Madewell

Merino Wool Sweater Maxi Dress

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j.crew

New Stevie Knee-High Pull-On Boots in Leather

Bordeaux Bag in Leather

Outfit #5

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(Image credit: J.Crew, Madewell)

Lastly, let’s explore a French-inspired slip-skirt outfit. French women have perfected the art of styling this sleek skirt silhouette, transforming it into a statement piece that looks rich and approachable. Their secret lies in skillfully pairing the skirt with elevated basics. For example, they often choose a fitted turtleneck sweater that hugs the body just right, an oversize coat for a sense of ease, and flat shoes for all-day comfort. For an added touch of style, they typically incorporate a palette of classic shades like soft camel, pristine ivory, crisp white, warm chocolate brown, and deep burgundy—which all harmoniously elevate the overall aesthetic.

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