I remember the first chilly afternoon that made me reach for my oldest, most oversized sweater. It wasn’t planned or calculated, just an instinct to pull something around me that felt comforting and familiar. The kind of piece that makes you exhale, feeling wrapped and safe against the early bite of autumn. Over the years, I realized these moments shape my entire approach to dressing once the leaves start falling.
Baggy outfits don’t just keep you warm, they invite a kind of gentle permission to breathe easy and move through the day with a quiet confidence. Maybe you feel it too, the way a loose cardigan or wide trousers can turn a simple Tuesday into something softer, almost like a pause in the chaos.
When I look back on the outfits that carried me through the coldest months, it’s always the cozy, oversized silhouettes that stand out. They speak to a desire for comfort but also a quiet style, never loud, always real. As soon as the first crisp winds of fall arrive, these pieces come out of hiding—ready to soften the transition into winter and add a little calm to blustery days.
So today, I want to share the looks that have warmed my autumns and winters alike, hoping they’ll add the same gentle ease to your wardrobe, and maybe even spark a few new favorites.
1. Oversized Knit Sweaters With Straight-Leg Jeans
Nothing says fall quite like a chunky knit. Oversized sweaters have this way of making you feel cocooned, without losing any of your style. Pairing a cable-knit pullover with straight-leg jeans creates balance, especially if you cuff the denim at the ankle and slip into chunky boots. The gentle bulk of the sweater plays well with classic denim, and suddenly, running errands feels like wandering through a cozy mountain town—even if you’re just on your way to the corner shop.
On days when I want to feel especially snug, I’ll layer a thermal shirt beneath the sweater. Textures become important in cold weather, and the softness against your skin can turn a rushed morning into something almost indulgent. Add a wool beanie and your favorite crossbody bag for a look that moves easily from morning coffee to afternoon strolls.
The trick is not to overthink it. An oversized sweater asks for little else, just let it drape and soften your silhouette, and enjoy the feeling of being gently swaddled.
2. Slouchy Cardigans and Maxi Skirts
I used to believe cardigans were only for lazy weekends, but a slouchy, longline cardigan paired with a maxi skirt changed my mind. The loose cardigan, falling almost to the knees, paired with a flowing skirt, creates movement in every step. Even on the greyest winter day, the sway of fabric adds a subtle sense of joy.
For extra warmth, I like to add a fitted turtleneck beneath the cardigan, then slip on thick tights and knee-high boots. Patterns can be playful here—a plaid skirt or a cardigan with bold buttons can make the look your own. A big tote slung over your shoulder holds everything you need, and the whole ensemble feels thoughtful without any sense of fuss.
Sometimes, I’ll add a leather belt at the waist if I want a bit more definition, but honestly, the beauty is in the relaxed, layered feel. It’s an outfit that travels easily from a coffee date to a casual meeting, carrying the spirit of autumn along with you.
3. Baggy Hoodies and Cargo Pants
Some days, nothing feels right except for a hoodie that’s at least two sizes too big. I learned early on that the best hoodies are borrowed—sometimes from a partner, sometimes from the men’s section—because the extra room feels protective. When paired with loose cargo pants, the effect is instantly effortless and a little bit tomboyish.
Cargo pants bring function to the table, with all their pockets and slightly rugged edge. They work well with a cropped tank or tee underneath, and you can finish the look with high-top sneakers or platform boots. Add a canvas backpack or a bright beanie to inject some personality.
When you’re headed out to meet friends or just need to feel comfortable running errands, this combo feels right. I love that it doesn’t try too hard—it simply lets you exist as you are, wrapped in softness with just enough attitude.
4. Wide-Leg Trousers and Cropped Puffers
Wide-leg trousers, especially in corduroy or wool, bring an old-school elegance to winter dressing. These pants pool softly at the ankle and move easily with every step. A cropped puffer jacket keeps things feeling fresh and modern, balancing the volume below with a more tailored shape above.
A ribbed turtleneck tucked in at the waist creates a clean line, while a chunky scarf adds both warmth and a pop of texture. When the temperature really drops, I’ll add thermal leggings beneath the trousers. Loafers or combat boots finish the look—something sturdy to ground the softness.
This pairing works just as well for work meetings as it does for weekends in the city. There’s a grown-up ease to it, the kind of outfit that reminds you of long afternoons spent window-shopping or catching up with friends in a favorite café.
5. Oversized Flannel Shirts and Leggings
Flannel shirts bring back memories of family apple picking trips and crisp Sunday mornings. When worn oversized, these shirts can double as light jackets, especially layered over simple black leggings. Add a pair of wool socks peeking out from sturdy ankle boots, and you’re ready for everything from a morning hike to a lazy afternoon at home.
The key to keeping this look intentional, not sloppy, is in the accessories. A chunky scarf or a bold, structured bag can anchor the relaxed fit of the shirt. Play with color—a classic red plaid, a soft pastel, or even a dark, moody check. Each one tells a slightly different story.
Sometimes, I’ll knot the shirt at the waist, or wear it open over a graphic tee. Either way, it’s an outfit that grows with you through the season, adapting to whatever the day brings.
6. Baggy Turtlenecks With Pleated Skirts
There’s something quietly elegant about a chunky turtleneck worn loose over a pleated midi skirt. The contrast of soft, oversized knits with structured pleats feels both modern and romantic. I’ve worn this look to art museums and winter parties, and it never fails to draw compliments.
Opaque tights and ankle boots keep your legs warm, while a delicate necklace or statement earrings add a touch of shine. Choose a turtleneck with extra-long sleeves you can pull over your hands—a small comfort that makes a big difference on a cold morning.
For an extra layer, throw on a tailored coat or a fuzzy vest. The swish of the skirt brings movement, while the baggy sweater keeps everything grounded and approachable.
7. Loose Jumpsuits and Chunky Cardigans
Jumpsuits are a little secret for those days when picking an outfit feels like too much. A baggy, soft jumpsuit in a thick jersey or brushed cotton wraps you in warmth from shoulder to ankle. Pairing it with a chunky, open-front cardigan brings added coziness and dimension.
On really cold days, I’ll slip a fitted turtleneck underneath or add fleece-lined leggings. Sneakers or Chelsea boots keep things practical, while a slouchy beanie or colorful scarf adds personality.
Jumpsuits carry a playful spirit. They let you move freely, sit cross-legged on the floor, or curl up on the couch. Yet, with the right accessories, you can take them straight out for coffee or brunch, feeling relaxed but still pulled together.
8. Baggy Denim Jackets With Knit Dresses
A knit midi dress forms the foundation for many fall and winter looks, especially when you want to feel both feminine and comfortable. Tossing a baggy denim jacket over a fitted or slightly relaxed knit dress creates an easy, casual vibe. The contrast of structured denim against soft knits is quietly striking.
Add knee-high boots or sneakers depending on your plans. On windier days, a thick scarf and wool hat finish things off perfectly. If you’re feeling playful, add a set of chunky earrings or a bold lip color.
This combination brings together the best of two worlds—ease and elegance. It travels well, whether you’re heading to the office or catching a late dinner with friends.
9. Oversized Sweatshirts and Biker Shorts
Sweatshirts with extra length and volume have a way of making even the dreariest morning feel a little softer. Paired with biker shorts, the look finds a balance between lazy-day comfort and off-duty model energy. Thick, textured socks and chunky sneakers round things out.
I started wearing this look on weekends at home, but quickly realized it was perfect for coffee runs and park walks too. Layering a long trench coat on top can bring just the right amount of structure.
This outfit is especially good for those unpredictable days when the weather shifts between warm sun and sudden chill. Just keep a pair of leggings handy in your bag, in case the temperature drops.
10. Baggy Wool Coats Over Relaxed Denim
A long, oversized wool coat feels like a warm hug every time you slip it on. Worn over relaxed denim and a soft cashmere sweater, this combination is timeless. I love how the coat’s gentle drape frames your figure without swallowing it whole.
Add pointed boots or clean white sneakers, a favorite tote, and you’re ready for any winter adventure. Some days, I’ll tuck a brightly colored scarf in my pocket for a burst of color when the skies feel especially grey.
With this look, you don’t need much else. The coat does most of the work, carrying you through the coldest months with quiet confidence.
11. Baggy Overalls With Turtlenecks
Overalls hold a special place in my heart, especially in heavier denim or corduroy for winter. Worn loose over a fitted turtleneck, they create a playful, almost nostalgic feel. High-top sneakers or lug boots add a bit of edge, while a thick knit beanie finishes things off.
Layering is easy—throw on an oversized flannel or puffer vest when the temperature dips. Overalls have a way of making you feel younger, lighter, ready for snowball fights or spontaneous hot chocolate stops.
If you’re not sure where to start, stick with dark-wash denim and a black or cream turtleneck. From there, let your accessories tell the rest of the story.
12. Boxy Blazers With Baggy Trousers
Nothing beats the confidence of a sharp blazer, but in colder months, I gravitate toward boxier fits. Worn over baggy trousers and a tucked-in tee or thin sweater, the look is both powerful and cozy. I love pairing this with sleek loafers or chunky boots.
Add a crossbody bag and simple jewelry to keep things modern. The blazer’s structure pulls the outfit together, while the trousers keep you relaxed and comfortable through meetings or errands.
Sometimes, a plaid or checked blazer brings just the right touch of vintage, making you feel like you belong in a classic movie.
13. Slouchy Sweater Dresses and Over-the-Knee Boots
Sweater dresses become a winter uniform, especially when they’re roomy and long enough to curl your legs under while sipping tea. Over-the-knee boots keep things chic and warm, adding just the right hint of polish.
A thin belt can add a bit of shape if you want, but I often leave it loose, letting the fabric drape naturally. Add a structured shoulder bag and a simple chain necklace for a finished look.
Sweater dresses work everywhere—from casual dinners to late-night strolls. They’re endlessly adaptable, always comfortable.
14. Baggy Sherpa Jackets With Joggers
Sherpa jackets have found their way into nearly every winter closet for good reason. Paired with loose joggers and a simple tee, the effect is pure comfort. I like to choose joggers in deep jewel tones or soft neutrals, depending on my mood.
Slip into sneakers or warm slippers if you’re staying in. A bright knit hat or fun socks can add a pop of color, making even the most casual look feel intentional.
This pairing is perfect for lazy Sundays, long road trips, or simply cozying up by the fire.
15. Oversized Button-Ups and Relaxed Knit Pants
Button-up shirts don’t have to feel stuffy. An oversized, crisp white shirt over relaxed knit pants brings a sense of ease and subtle sophistication. Roll the sleeves, half-tuck the hem, and add simple gold hoops for a polished touch.
This look is ideal for working from home or grabbing a late breakfast at your favorite spot. It’s gentle, a little bit dreamy, and incredibly comfortable. On colder days, drape a cable-knit sweater over your shoulders or wrap up in a heavy wool scarf.
If you’ve ever hesitated to embrace baggier styles, start here. The blend of structure and softness is easy to love.
