10 Best Plus Size Winter Outfits Casual Ideas That Look Chic & Cozy
Winter has always been one of my favorite fashion seasons. The layers, the textures, the cozy vibes—I live for it. But as someone who writes (and shops) endlessly about fashion, I know it can sometimes feel like plus size women don’t get enough love when it comes to casual winter outfit inspiration. That’s why I put together this list of the 10 best plus size winter outfits casual ideas that look chic & cozy—curated from trends I’ve tried myself, seen on stylish friends, and researched deeply.
These outfits work across occasions: work, going out, business attire, dressy evenings, or just running errands in the cold weather. Whether you’re curvy, chubby, over 50, or looking for chic outfit ideas as a Black woman, you’ll find inspiration here that’s inclusive and versatile.
Let’s dive into these outfit formulas that blend comfort with chic style, while making sure you stay warm all winter long.
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1. Classic Leggings + Big Sweater + Boots Combo
If you ask me, this is the ultimate winter uniform. When I’m rushing out the door but still want to look pulled together, I grab a pair of black leggings, throw on a big sweater, and finish it off with ankle or knee-high boots.
Why it works: Leggings hug your curves without being restrictive, while a chunky knit balances the silhouette. Boots add that polished finish.
When to wear: Perfect for errands, coffee dates, or even casual Fridays at work with the right accessories.
Styling tip: Add a puffer jacket on top for extra coziness.
2. Jeans + Trench Coat + Sneakers for Street Chic
This is one of my personal go-to looks when I want to feel effortlessly stylish. Pairing straight-leg jeans with white sneakers and layering a trench coat instantly gives you that street style edge.
Why it works: It’s laid-back but chic, comfortable but polished.
When to wear: Ideal for everyday wear, city walks, or even a casual business meeting.
For curvy women: Choose high-waist jeans for a flattering fit.
3. Midi Skirts with Boots + Sweater Layers
One of the chicest plus size winter outfits casual ideas I swear by is pairing a flowy midi skirt with a chunky sweater and tall boots. It strikes the perfect balance of feminine and cozy.
Why it works: Midi skirts move beautifully, and boots keep your legs warm.
When to wear: Perfect for a dressy lunch date, weekend brunch, or office outfit.
Personal touch: I wore this combo last December to a winter baby shower and got endless compliments—it’s one of those outfits that feels put-together without trying too hard.
4. Sweater Dress + Knee-High Boots
Every winter wardrobe needs a sweater dress. It’s one of the most versatile pieces: chic enough for going out, cozy enough for everyday errands, and polished enough for business attire if styled right.
Why it works: The dress keeps you warm while elongating your frame, and knee-high boots add sophistication.
When to wear: Anywhere from office days to holiday dinners.
Styling tip: Add a belt to cinch your waist if you want more shape.
5. Puffer Jacket + Leggings + Sneakers Off-Duty Look
Here’s where comfort meets casual streetwear chic. Pair your leggings with an oversized big sweater, add sneakers, and top it off with a puffer jacket.
Why it works: It’s relaxed yet trendy, especially in neutral tones like black, beige, or olive.
When to wear: Grocery runs, coffee catch-ups, or airport outfits.
Curvy fashion tip: Opt for a slightly cropped puffer jacket to highlight your waistline.
Amazon Product Recommendation #1: Columbia Women’s Heavenly Long Hooded Jacket
I’ve tested so many puffers, and this one is a game-changer. The Columbia Heavenly Puffer is lightweight, water-resistant, and designed with Omni-Heat thermal reflective lining to keep you warm without feeling bulky. Perfect for pairing with leggings or jeans in any of the looks above.
Get it on Amazon here and stay chic while conquering the cold!
6. Business Chic: Blazer + Jeans + Boots
Not every winter outfit has to be oversized and casual—sometimes you want something smart yet wearable. A structured blazer, paired with jeans and ankle boots, creates the perfect business casual attire.
Why it works: You look professional without feeling stiff.
When to wear: Work meetings, client lunches, or even semi-dressy events.
For women over 50: Choose tailored blazers in neutral shades for timeless chic.
7. Trench Coat Over a Midi Dress + Ankle Boots
Layering a trench coat over a dress is the kind of outfit that screams effortless chic. It’s also a great way for black women to incorporate bold prints or bright colors in dresses, balanced with a neutral trench.
Why it works: The coat adds structure, while the dress adds softness.
When to wear: Date nights, office days, or dressy events.
Curvy fashion tip: Midi dresses with defined waists work beautifully under trench coats.
Amazon Product Recommendation #2: London Fog Women’s Double-Breasted Trench Coat
I’ve had this trench for years, and it never goes out of style. The London Fog trench coat is lightweight, water-resistant, and lined for warmth—perfect for layering over dresses, skirts, or even jeans. A true timeless staple for winter fashion.
Shop it on Amazon here to elevate your winter wardrobe instantly!
8. Oversized Big Sweater + Midi Skirt + Sneakers
This outfit has a playful, youthful vibe that I love. Tucking the front of a chunky big sweater into a midi skirt and pairing it with trendy sneakers is modern, chic, and perfect for casual days.
Why it works: Mixes structure and flow, comfort and style.
When to wear: Shopping days, museum visits, or casual Fridays at work.
Personal touch: I wore this outfit for a weekend trip in Paris—it felt comfy for walking yet stylish in photos.
9. Chic Going Out Look: Leather Leggings + Dressy Top + Heeled Boots
When you’re heading out for dinner or a night out in the winter, you want something chic but warm. Enter leather leggings, a dressy blouse or top, and heeled boots.
Why it works: Leather leggings add instant edge, while boots keep it classy.
When to wear: Going out with friends, date nights, or holiday parties.
Curvy/chubby style tip: Faux leather leggings with tummy control are super flattering.
Amazon Product Recommendation #3: Spanx Faux Leather Leggings
These are honestly a holy grail for curvy women. The Spanx faux leather leggings are smoothing, stretchy, and add instant chic to any outfit—whether with a big sweater or a dressy top. They’re warm, versatile, and one of my winter must-haves.
Grab your pair on Amazon here and upgrade your winter outfits instantly!
10. Layered Workwear: Sweater + Button Down + Trench Coat + Trousers
For those days when you need business attire that’s practical for cold weather, this layered combo is a lifesaver. Think trousers, a crisp button-down shirt, a warm sweater on top, and a sleek trench coat as the final layer.
Why it works: Layers keep you warm while giving a smart, professional vibe.
When to wear: Office days, presentations, or business travel.
For women over 50: Stick to classic color palettes like navy, camel, and black for timeless chic.
Conclusion
Fashion should never feel limiting—especially not in winter. These 10 plus size winter outfits casual ideas prove that you can stay cozy, look chic, and express your personality no matter the temperature. Whether you’re reaching for leggings, sneakers, boots, a trench coat, a puffer jacket, a sweater dress, or midi skirts, there’s a formula here that works for curvy and chubby fashion lovers everywhere.
The truth is, winter dressing is all about confidence and creativity. Personally, writing this article reminded me of my own journey—learning to embrace layers, play with proportions, and finally realizing that style has no size.
So next time you’re standing in front of your closet on a chilly morning, just remember: you don’t have to choose between chic and cozy. With these outfit ideas—and maybe a few smart staples from Amazon—you can have both.
Stay warm, stay stylish, and most importantly, stay confident.