The cold weather is here and it’s time to break out the sweaters, boots, and layers!
As a midsize fashionista, you want to stay warm and cozy all winter long while still looking cute and put together.
The key is finding the right balance of texture, color, and accessories to create an outfit that is both functional and fashionable.
Slouchy Sweater + Skirt
My midsize winter outfit idea pairs a slouchy sweater with a button-up skirt.
Choose an oversized sweater in a chunky rib or cable knit.
Opt for a slouchy silhouette that hits at mid-thigh in tan, gray, cream or white.
Next, layer a button-up denim, corduroy, or wool skirt underneath. The wrap style creates a flattering A-line silhouette.
Pair with leather boots or booties to tie the outfit together.
Finish with a colorful beanie, circle scarf, and saddle bag for a casual weekend vibe. This tomboy chic outfit works well for running errands or meeting up with friends.
You’ll stay nice and cozy with the oversized sweater while the button-up skirt lends polish and shape.
It’s the perfect easy, winter-ready outfit for weekends and beyond!
Turtleneck + Wide Leg Pants
For a bit more polish, style a fitted turtleneck bodysuit with wide leg trousers. Look for a ribbed turtleneck in a bold hue like emerald green or cobalt blue to make a statement.
Pair with high-waisted, wide leg pants in a complementary solid color. The voluminous legs on the pants will balance your hips while cinching the waist.
Keep the rest of the look minimal with simple gold hoops, a watch, and heels or boots. Finish with a wool coat in camel or gray tailored to your figure.
The monochromatic color scheme makes this outfit look luxe and expensive for any occasion from the office to dinner out. The stretch bodysuit and flowy pants combination is comfortable for all-day wear.
Textured Sweater + Paperbag Pants
For the ultimate in comfort and style, try pairing a textured sweater with paper bag pants. Look for a sweater in an on-trend waffle or honeycomb knit fabric for cozy texture.
Tuck it into high-waisted paperbag waist trousers for a pulled-together casual chic vibe. The paperbag waist is designed to cinch in at the narrowest part of your waist for a flattering silhouette.
Choose a pair with adjustable ties or belts at the waist to customize the fit.
A cropped wide-leg cut is most flattering for a medium frame. Ground the look with suede ankle booties and add a baker boy cap for a modern finish. Carry a tote bag big enough for an extra sweater or all your daily essentials.
This outfit works for weekend coffee dates or running errands in comfort and style.
Sweater Dress + Tall Boots
For the easiest outfit ever, just throw on a sweater dress and boots!
Look for a sweater dress that hits right at the knee in a super soft wool or cashmere blend. Go for a neutral camel or grey to pair with everything.
Then simply add tall boots.
Over-the-knee styles elongate the legs, while a low block heel gives you lift without discomfort. A pair in black or brown leather boots grounds the look.
Finish with a colorful circle scarf and crossbody bag. You’ll be cozy and chic in this monochromatic outfit that takes minutes to put together.
It’s perfect for a low-key brunch or running around doing errands. Dress it up with a long coat and heels for a dinner date night.
Corduroy Pants + Mock Neck
Corduroy pants are back in a big way for winter!
The retro fabric adds cozy texture to any outfit.
Go for a high-waisted, wide-leg pair in a camel or forest green hue. Pair with a fitted mock neck sweater in a coordinating color or white.
Tuck just the front of the sweater in to define your shape while keeping the rest out for comfort and style. Finish with ankle booties or slip-on loafers and a crossbody bag.
Add a fuzzy teddy coat in a bright color like fuchsia or cobalt for a fun pop. This 70’s inspired outfit is both comfortable and chic for running errands or meeting up with friends. The mock neck adds warmth and the corduroy makes a retro statement.
Cozy Midi Dress + Tall Boots
My favorite outfit formula for winter is a cozy midi dress paired with tall boots. Look for a sweater dress made from a chunky ribbed knit or brushed fabric that hits right below or at the knee.
Neutral hues like camel, gray, or black make the dress versatile to pair with different boots and coats. Speaking of boots, go for either a slouchy or fitted leather style.
Over-the-knee boots add drama while a chunky lug sole or low block heel is comfortable enough for all-day wear. Finish with an oversized scarf wrapped with carefree elegance and a saddle bag.
You’ll be cozy and polished from coffee dates to running errands. A midi dress and boots outfit is my winter go-to for comfort and style.
Cozy Knits + Paperbag Pants
An oversized sweater paired with paper bag pants creates the perfect slouchy weekend look.
Choose an oversized sweater in merino wool or a chunky knit that hits at mid-thigh. Tuck just the front into a pair of high-waisted paper bag pants for a bit of shape.
The billowy legs of the paper bag silhouette will balance your lower half. Stick to neutral earth tones like cream, tan, grey, and brown for a calming palette.
Finish with ankle booties and a circle crossbody bag. Don’t be afraid to play with textures and proportions. An exaggerated slouchy outfit is actually very chic with refined winter layers.
Throw on a wool coat and scarf to finish. You’ll be stylish and comfy all day long.
Turtleneck Bodysuit + Faux Leather Leggings
Faux leather leggings are a wardrobe staple that instantly polish any outfit.
For a sleek silhouette, pair them with a fitted turtleneck bodysuit. Look for one with long sleeves and a thong bottom in black, white, or navy.
The stretchy ribbed fabric hugs your curves in all the right places for a flattering foundation. Next, pull on high-waisted faux leather leggings for an edgy touch.
They look just like real leather but are comfortable with a bit of stretch. Accentuate your shape by tucking just the front of the bodysuit into the waistband.
Then add pointed toe ankle booties, a watch, and rectangular sunglasses. Bring a top handle bag like a mini duffle to carry essentials. You’ll look chic and feel amazing in this easy yet sexy outfit.
Cream Teddy Coat + Knit Dress
Make a statement by pairing a cream teddy coat with a knit dress.
Start with a fuzzy textured teddy coat in a rich cream hue. The plush fabric instantly makes any outfit look luxurious.
Underneath, wear a midi sweater dress made from a ribbed knit.
Turtleneck and long sleeve styles will keep you extra cozy.
Form-fitting silhouettes accentuate your waist. For contrast, go for a dress in classic black, charcoal grey, or forest green.
On your feet, add suede knee boots and matching leather gloves. Carry a hobo bag big enough for all your daily essentials. Walk out the door looking polished without sacrificing comfort in this outfit that makes a luxe statement.
Oversized Blazer + Joggers
Give your casual wear an upgrade by pairing joggers with a tailored oversized blazer. Start with joggers or harem style sweatpants in black, grey, or navy.
Look for tapered legs and a drawstring waist for comfort. On top, layer an oversized blazer in plaid, houndstooth, or a bright color like fuchsia.
Leave it unbuttoned and slightly long for that cool, carefree vibe. Next add a graphic tee or cropped hoodie underneath. Finish with white sneakers or ankle booties and a circular crossbody bag.
This athleisure chic outfit works for a coffee date or running errands. You’ll look put-together but feel as comfy as you would in sweats.
Ponte Pants + Turtleneck
For a polished everyday look, you can’t go wrong with ponte pants and a turtleneck. Ponte knit pants have a bit of stretch for comfort and hold you in while smoothing any lumps or bumps.
Pair them with a fitted long sleeve turtleneck bodysuit for a streamlined silhouette. Tuck the bodysuit into the pants to accentuate your waist.
Monochromatic colors like olive green, navy, or burgundy work well. Finish with Chelsea boots or block heels and a hobo or saddle bag. Add a longline wool coat for warmth and elegance.
This outfit works for the office, running errands, or dinner with minimal effort. The turtleneck and ponte pants combination is equal parts cozy and chic.
Cowl Neck Sweater + Faux Leather Leggings
For an outfit that’s equal parts cozy and chic, pair a cowl neck sweater with faux leather leggings.
Choose a cowl neck sweater that is fitted through the shoulders and arms to balance the draped neckline.
Tuck just the front into high-waisted faux leather leggings for a little extra polish.
The super sleek leggings create contrast with the soft sweater fabric. Finish the look with ankle booties or Chelsea boots. Accessorize with a fedora style hat for extra flair.
Grab a structured top handle bag big enough for all your daily essentials. Stay warm and stylish running errands or when meeting friends in this effortlessly cool winter outfit.
The mix of textures gives visual interest while the neutral color scheme makes it easy to wear again and again.
Western Boots + Printed Midi Dress
Leaning into the western boot trend this winter?
Then pair them with a printed midi dress for a feminine-meets-rugged vibe. Look for a midi dress with long sleeves, a defined waist, and a skirt that hits at or below the knee.
A floral, paisley, or gingham print adds visual interest. Pair with slouchy or fitted cowboy boots. Knee high styles balance a shorter frame.
Then layer on a shearling or fuzzy coat in camel or taupe. Finish with a crossbody bag with a long strap you can wear across your body.
Walk out the door looking sweet and rugged in one easy step. You’ll be ready for anything from coffee dates to holiday parties in this pretty yet practical outfit.
With the right blend of comfy fabrics, versatile silhouettes, and stylish accessories you can stay warm while looking amazing.
Just add your favorite winter coat and you’re ready to take on anything while staying true to your cute and cozy style. What outfit combo are you most excited to try?
Get ready to beat the winter style blues and embrace the cold in fashionable comfort!
