I still remember the first winter I moved to the snowy Midwest from sunny California.
I stepped outside in my usual jeans and light sweater, only to be met with a blast of frigid wind!
That’s when I realized I needed to overhaul my winter wardrobe.
After some trial and error, I’ve found go-to outfits that keep me warm and stylish all season long.
The key to staying cozy and looking cute is layering pieces that provide warmth while allowing you to mix and match.
Investing in a few versatile cold weather staples allows you to create multiple outfits from just a few items.
Oversized Wool Coat
An oversized wool coat instantly polishes any outfit while keeping your core toasty.
Look for one that hits at least mid-thigh for maximum cold blocking abilities.
I love pairing mine with skinny jeans and boots for an effortlessly chic vibe.
Pro tip: SIZE UP for room to layer underneath.
Go for a neutral color like black, gray, or camel that pairs well with everything in your closet.
Look for a wool blend fabric with at least 20% wool for warmth without crazy itchiness.
My favorite brands for oversized wool coats are Everlane, Aritzia, and J.
Crew – the quality is amazing for the price.
If you invest in one during end of season sales, you can often score deals under $200.
For extra warmth, look for a quilted or faux fur lined style.
I layer mine over hoodies, chunky knits, even lightweight down puffers when it’s super frigid out.
An oversized silhouette balances out all your bulkier layers.
Cinch the waist with a belt for a more tailored chic vibe.
I get so many compliments whenever I wear my black mid-thigh wool coat.
Chunky Knit Sweater
A chunky sweater is a winter wardrobe essential.
Cozy and insulating while still stylish, it pairs perfectly over a long sleeve tee or under a denim jacket.
For extra warmth, go for a turtleneck style.
I like to throw mine on with leggings and booties for a cute weekend errand look.
Stick to natural fibers like wool, alpaca, cashmere blends for best warmth.
Fast fashion acrylic sweaters may look cute but don’t provide much insulation.
Go for a relaxed, oversized fit to allow for layers underneath.
I love wearing mine under leather and denim jackets when I need an extra layer of coziness.
neutrals like black, gray, camel, and white match everything and are so chic.
Cable knit, ribbed textures and cowl neck styles balance out the oversized fit.
Pair with skinny jeans, leggings or boots for an effortless weekend look.
I pretty much live in my oversized gray chunky pullover once the weather dips below 60 degrees.
Faux Fur Vest
Elevate any outfit with a faux fur vest.
Great for layering over hoodies, sweaters, or jackets, it adds a stylish touch while helping contain body heat.
I love rocking mine over a thermal henley with black jeans and Chelsea boots for a model-off-duty vibe.
Go for a cropped style that hits at the waist or hips for a universally flattering silhouette.
I like to throw mine on over chunky knits and thermals when I need extra core warmth but don’t want to rock a full jacket.
It instantly dresses up any casual outfit and makes you look pulled together.
The plush faux fur traps heat in to keep your core, back and shoulders toasty.
A black or camel vest matches everything and transitions so nicely from day to night.
I get so many compliments whenever I style my black faux fur vest over jeans and a thermal long sleeve.
It’s my styling secret for looking polished even when I’m freezing!
Puffer Coat
When temps really dip, you need serious insulation.
Enter the puffer coat, aka your new cold weather BFF.
Belted styles are super flattering and cinch the waist.
Go for a longer length for maximum coverage.
I always get compliments when I wear my black puffer over skinny jeans with a beanie and scarf.
Look for a mid-thigh to knee length silhouette for the most warmth.
Quilted styles with down or synthetic down fill provide lightweight, packable insulation.
I save my long black Hooded puffer for when temps dip into the 20s and below – it’s like wearing a sleeping bag!
Oversized puffers are totally on trend and balance out your winter layers beautifully.
Cinch in the waist with a belt or faux fur pom pom pullstrings for a more flattering silhouette.
Toss it on over leggings and a turtleneck sweater dress for instant warmth and style.
My go-to brands for quality puffer coats are Patagonia, The North Face, and Aritzia.
Sherpa Lined Jean Jacket
For a slightly more polished look than a puffer, try a sherpa lined jean or leather jacket.
The cozy fleece lining keeps you so toasty without adding bulk.
I throw on my classic Levi’s denim version over hoodies on super cold days.
It never fails to keep me warm and stylish.
The sherpa lining instantly turns your denim jacket into a wearable blanket – genius!
Levi’s, Topshop, and Madewell all make quality versions that last for years.
Styling a sherpa jean jacket over a thermal tee and leggings creates the coziest weekend look.
For extra warmth, size up to accommodate layers underneath.
I love the contrast of the rugged denim exterior with the plush sherpa lining.
It’s my favorite transitional piece from fall into deep winter – so versatile!
Fleece Lined Leggings
If your legs always feel cold, it’s time to invest in some fleece lined leggings.
They provide an extra layer of insulation under pants or sweater dresses.
I love wearing mine under ripped skinny jeans with booties and an oversized cardigan for a winter weekend look.
The plush fleece lining instantly adds warmth without sacrificing a polished look.
They don’t add extra bulk under trousers like regular leggings.
My favorite fleece lined leggings are from Spanx – they come in great basic colors.
Layer them under skirts, dresses or jeans when cold weather strikes for instant insulation.
They also make a great base layer for snow pants and winter gear when braving the elements.
I pretty much live in my black fleece lined leggings from November through March!
Thermal Base Layers
Don’t underestimate the power of base layers!
A thermal henley, long sleeve tee, or leggings underneath your outfit provides insulation without adding bulk.
I always wear a thin thermal top under sweaters or flannels for an extra boost of warmth.
You can even throw a thermal under jeans for legs that won’t freeze.
Look for lightweight, moisture-wicking styles so you don’t overheat indoors.
Brands like Patagonia, Under Armour and Uniqlo make ultra-soft thermals in versatile solids.
Layer them under button downs, sweaters, flannels for added insulation.
Thermal leggings under pants provide an extra layer of warmth for your legs.
I love wearing a black thermal tee under chunky sweaters or jean jackets when temps dip.
It keeps me so toasty without adding a ton of extra bulk.
Oversized Blazer
An oversized blazer polishes up any outfit while adding a layer of warmth.
Throw it on over sweaters, flannel button downs, or hoodies.
I love wearing mine over skinny jeans with a turtleneck sweater underneath.
The slouchy silhouette keeps the look casual and cozy.
Go for a thick textured fabric like wool, tweed or textured knit for warmth.
Blazers with shoulder pads balance proportions and cinch the waist.
Boyfriend and oversized styles allow room for layers without looking bulky.
I love rocking an oversized gray plaid blazer over jeans and a hoodie when I want to elevate a casual look.
It keeps me so warm while still looking polished and stylish.
Corduroy Pants
Corduroy pants provide warmth and texture to any winter outfit.
They look chic with chunky knits, fleece pullovers, and turtlenecks.
I’m currently loving wide leg corduroy pants paired with a cropped sweater and Chelsea boots.
The 70s vibe keeps me feeling stylish as the cords keep my legs toasty.
Look for a mid to high waisted cut – it’s the most flattering for every body type.
I love rocking black, camel and olive green cords – they match everything!
The thick corduroy fabric is perfect for trapping heat close to your legs.
Pair with boots, loafers or white sneakers depending on the occasion.
I pretty much live in cords and sweaters when temps start dropping.
Sweater Dress
For an effortlessly chic cold weather look, you can’t go wrong with a sweater dress.
Pair with tights or leggings and knee high boots for easy elegance.
I like to add a faux fur vest on top on really frigid days.
The sweater dress keeps my core warm while the vest traps in body heat.
Go for soft, cozy fabrics like wool, cashmere or angora blend.
Mock neck, turtleneck or cowl neck styles provide additional neck warmth.
Look for thicker knits rather than lightweight material for better insulation.
Midi lengths provide more coverage while mini sweater dresses pair perfectly with warm tights.
I love rocking an oatmeal colored turtleneck sweater dress with black tights and tall boots on cold winter days.
Over the Knee Boots
A pair of over the knee boots instantly dresses up any outfit.
Just add leggings or skinny jeans tucked in.
Not only do they elongate your legs, they also keep your lower legs extra warm and toasty.
I love the model off duty vibe I get by pairing mine with an oversized sweater and puffer vest.
Look for a pointed or rounded toe – they are the most universally flattering.
Black, brown, and tan over the knee boots will match everything in your closet.
The extra tall shaft provides coverage and warmth to your lower legs.
Pair with cropped jeans or sweater dresses to show off the sexy shaft height.
I feel like a supermodel whenever I style mine with an all black look of skinny pants, turtleneck and blazer.
Fleece Lined Tights
If regular tights just don’t provide enough warmth, it’s time to try fleece lined.
They add an extra insulating layer under dresses, skirts and shirts when it’s super chilly out.
I wear mine with sweater dresses and miniskirts in the winter to keep my legs from freezing.
They provide warmth while still looking polished.
The plush fleece lining makes it feel like you’re wearing sweatpants under your outfit!
Look for control top styles to smooth your shape under clingy knits and dresses.
I love rocking black fleece lined tights under mini skater dresses and skirts in the winter.
They allow me to wear my favorite cold shoulder or short sleeve dresses all season long without freezing.
Fleece lined tights are a winter styling essential for comfort and warmth!
Ponte Knit Pants
Ponte knit pants have become my new winter wardrobe staple.
The thick stretchy fabric is smoothing while providing warmth that regular trousers just don’t have.
Pair them with sweaters, blouses or bodysuits to stay toasty in style.
I love wearing ankle ponte pants with over the knee boots and a turtleneck for a foolproof cold weather outfit.
Look for styles with a touch of stretch for comfort – they shouldn’t feel restrictive.
A classic black ponte pant matches everything and transitions beautifully from day to night.
The thick pont knit fabric smooths and slims your shape while keeping you cozy.
Dress them up with heels and blazers or down with sneakers and sweaters.
I pretty much live in ponte pants paired with tall boots and chunky sweaters once winter hits!
Plaid Flannel
A cozy flannel shirt instantly feels like a warm hug.
Layer one over a thermal or tee for extra insulation.
To avoid looking overly lumberjack-ish, choose fitted styles and pair with feminine pieces like skinny jeans or a mini skirt.
I always get compliments when I wear my red buffalo check flannel over a thermal tee and leggings.
Look for soft cotton blends – they get even cozier the more you wash them.
Oversized styles allow room for layers underneath.
Pair with jeans, leggings, thermal tops and boots for an effortless weekend look.
Rolling the sleeves and leaving it unbuttoned keeps the vibe casual and cool.
My go-to way to wear flannel is over a thermal henley and jeans with ankle booties.
Puffer Vest
For stylish warmth, you can’t beat a puffer vest.
It provides core insulation without adding as much bulk as a jacket.
I wear mine over hoodies, chunky sweaters and thermals nearly every day once it gets really frigid out.
It adds a sporty-chic element while containing precious body heat to keep me toasty.
Go for a longer length that hits at least at your hips for the most coverage.
Down or synthetic down fill provides lightweight warmth that you can layer or wear alone.
Oversized puffer vests balance proportions and create that cool model off duty vibe.
I love rocking my black hooded puffer vest over jeans and a turtleneck when I want to look stylish and stay warm.
It’s my winter wardrobe MVP for sure!
Faux Shearling Coat
When temps get Arctic, nothing keeps you as warm as shearling.
Faux versions are a stylish way to get the teddy bear look without the price tag.
The plush lining instantly heats up your core.
Topping a sweater dress with a shearling coat creates a cute winter silhouette.
Stay so cozy while looking totally on trend.
Look for a midi length shearling coat – it provides maximum warmth and coverage.
The fluffy texture and oversized fit create such stylish drama.
Tonal brown or tan shearling coats complement everything in your wardrobe.
Cinch in the waist with a belt if the oversized silhouette is overwhelming.
I love dressing up casual outfits like joggers and hoodies with my tan faux shearling coat.
It instantly takes my look from drab to fab!
Oversized Button Down
An oversized button down provides extra warmth when worn layered over a sweater or thermal top.
Choose a thick flannel or wool style for maximum coziness.
I love wearing mine untucked over leggings with knee high boots.
The menswear vibe always looks effortlessly chic while the oversized fit traps in body heat.
Look for soft brushed cottons, thick flannels and wool blends.
Plaids, buffalo check and preppy stripes create fun visual interest.
Size up at least one size, even two for an intentionally roomy borrowed-from-the-boys fit.
I always style mine with leggings or skinny jeans to balance the oversized proportions.
My go-to fall/winter look is a red buffalo check button down over a black thermal henley, black jeans and boots.
It’s cozy meets cool vibes all day!
With the right staple pieces, you can stay toasty while still looking cute all winter long.
Invest in some key cold weather layers in styles you can mix and match for multiple outfits.
With a little creativity, you can bundle up in style without sacrificing your personal aesthetic.
Now if you’ll excuse me, I need to dig my shearling coat out of storage!
