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
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.
j.crew
Pullover Sweater With Scarf
Madewell
The Harlow Superwide-Leg Trouser in Brushed Twill
Madewell
The Grayson Penny Loafer
j.crew
Berkeley Bucket Bag in Leather and Suede
Outfit #2
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.
j.crew
Garçon Classic Shirt in Cotton Poplin
j.crew
High-Rise Straight Jean in 1996 Semi-Stretch
Madewell
Triple Metal Keeper Belt
Madewell
The Dimes Stiletto-Heel Ankle Boot
j.crew
Metallic Chainlink Necklace
Outfit #3
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.
j.crew
Cashmere Shrunken Crewneck Sweater
madewell
The ’90s Straight Jeans
j.crew
New Stevie Ankle Boots in Leather
j.crew
Metallic Ball Earrings
Outfit #4
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.
Madewell
Merino Wool Sweater Maxi Dress
j.crew
New Stevie Knee-High Pull-On Boots in Leather
Outfit #5
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.
j.crew
Daphne Topcoat in Italian Boiled Wool
J.Crew
Tissue Crepe Turtleneck
Madewell
Satin Maxi Slip Skirt
Madewell
The Greta Ballet Flat
Madewell
Cable-Knit Trouser Socks