Heading out to your favorite bar or lounge is a great way to get out of the house and enjoy time with friends even when it’s cold outside.
The key is choosing an outfit that keeps you warm but also stylish.
After all, the bar scene is all about looking chic.
Why bundle up in a puffy coat and snow boots when you can rock a sleek jacket and heeled booties?
With some clever layering and the right accessories, you can look incredibly fashionable while staying cozy.
Many incorporate on-trend pieces but also timeless staples you’ll wear for seasons to come.
So check your calendar for the next girls’ night or date night, and get ready to bundle up in style.
Leather Leggings and Drapey Blouse
If you want to look edgy yet elegant for cocktails this winter, consider leather leggings paired with a drapey silky top.
Faux leather or vegan leather leggings have become a winter staple, ideal for nights when you want to show off your curves without freezing.
Choose a pair in a rich wine color or metallic for a luxe vibe.
On top, go for a silky blouse in a jewel tone like emerald green or sapphire blue. Look for one with billowy long sleeves, a loose fit through the body, and subtle sheen.
The fluid fabric is flattering and brings movement when you walk. For more coverage, you can add a lacy cami underneath.
Finish this outfit with pointy-toe ankle booties, a chained shoulder bag, and sparkling drop earrings. You’ll look sleek yet romantic for an intimate date night at a low-lit lounge.
A bold lip color like berry or burgundy ties the entire look together beautifully.
Faux Fur Jacket and Dark Jeans
For casual drinks with your crew, you want a outfit that’s laidback but still chic.
A cozy faux fur coat paired with dark skinny jeans is the perfect combination.
The fuzzy coat keeps you warm and adds a glam, retro vibe, while the jeans make it relaxed enough for a neighborhood bar.
Look for a faux fur coat in a hip length with a spread collar and front zip closure.
Neutral shades like cream, grey, or tan are endlessly versatile. Make sure to layer a chunky knit turtleneck underneath in a coordinating color.
On the bottom, go for black or dark blue skinny jeans – they elongate your legs and work for both day and night.
Tuck the jeans into knee-high slouch boots for extra style points. Accessorize with a beanie and circle crossbody bag to finish this casually cool winter outfit.
Plaid Button-Up and Skirt
For a flirty vibe, pair an oversized plaid button-up with a mini skirt and knee boots.
Start by choosing a long sleeve menswear-inspired button-up shirt in classic checkered plaid.
Look for one in soft flannel with relaxed arms and minimal shaping – it’ll add a tomboy feel while keeping you cozy.
Next, choose a skirt made of a thick textured fabric like tweed or textured wool to retain heat.
Consider a high-waisted A-line mini skirt for a leg-lengthening effect. Tuck in your plaid shirttail to show the waist.
Then, slip on a pair of flat or low block heel knee boots.
A utilitarian combat or slouchy suede style balances the femininity of the mini. Finish with a beanie and you have a cute, casual outfit perfect for a low-key neighborhood spot.
Fleece-Lined Tights and Wrap Dress
Stay warm while looking elegant in a wrap dress styled with fleece-lined tights and booties.
A wrap dress cinches at the waist to show off your shape in a subtly sexy way that’s ideal for cocktails. Look for one with long sleeves in a rich, wintry hue like crimson, emerald, or sapphire.
Since bare legs are out this time of year, layer in fleece-lined tights. The plush inner lining feels like you’re wearing leggings while maintaining the polish of tights.
Choose an opaque black pair that elongates your legs underneath your dress.
Finish the outfit with heeled booties that complement your dress color, like black suede. A metallic shoulder bag and sparkly drop earrings complete this fail-safe winter cocktail outfit.
You’ll look festive yet refined strolling into the bar.
Distressed Jeans and Ballet Flats
On evenings when you want to go casual without compromising style, consider teaming distressed boyfriend jeans with ballet flats and a moto jacket.
Light wash denim with intentional rips and fraying has a grungy feel that downplays the outfit for a dive bar or pub.
Pair it with soft black leather ballet flats, which are dressier than sneakers but still comfortable for all-night wear. Finish with a classic black leather moto jacket – it pulls together the edgy and feminine elements into one cohesive look.
Underneath, wear a vintage band tee to tap into the outfit’s rocker chic vibe.
A crossbody bag and beanie cap off the outfit with a laidback finishing touch.
It’s the perfect casual-cool ensemble for a pint and games like pool, darts, or shuffleboard.
Wide-Leg Jumpsuit and Heels
Make a dramatic entrance in a wide-leg jumpsuit and strappy heels.
Look for a sleeveless jumpsuit with flowing wide legs, like a halter or keyhole front style.
Solid black is universally flattering, but you could also try an on-trend deep berry or forest green hue.
Pair it with your boldest pair of strappy heels – think citron snake print, glittery gold, or neon pink.
The juxtaposition of the modem, wide-leg jumpsuit with attention-grabbing heels makes for a showstopping yet effortless outfit.
Layer in gold statement earrings, a black leather clutch, and a moto jacket draped over your shoulders.
Pull your hair up in a sleek high ponytail to showcase the neckline of the jumpsuit.
You’ll feel sexy and glamorous as you turn heads on the dance floor or sip martinis fireside.
Fuzzy Sweater Dress and Over-the-Knee Boots
Look darling and feel cozy by pairing an fuzzy sweater dress with suede over-the-knee boots.
A sweater dress made from soft chenille or boucle yarn makes you want to curl up with a cocktail by the fireplace.
Choose one with long sleeves in a neutral solid hue like ivory, gray, or black.
Then pull on buttery soft suede over-the-knee boots in black or tan.
The thigh-high silhouette lengthens your legs while keeping you warm. Finish with a colorful circle scarf loosely wrapped around your neck. It adds a fun pop of color like fuchsia or cobalt blue.
Stash your essentials in a small wristlet or crossbody bag you can easily grab for quick trips to refresh your drink. With this outfit, you’ll be stylish, snug, and ready for a chilly winter night out.
The boots easily transition the sweater dress from day to evening.
Roll Neck Sweater and Slip Skirt
For trendy vintage appeal, pair an oversized roll neck sweater with a satin slip skirt and loafers.
A slouchy ribbed roll neck sweater billows for a chic baggy silhouette. Opt for one reaching mid-thigh in a neutral like ivory, black, or heather gray.
On bottom, contrast the oversized top with a sleek straight slip skirt that hits just below the knees.
Look for satiny fabrics with an adjustable spaghetti strap.
A solid black is classic, but don’t be afraid to try an emerald green jewel tone.
Ground the look with menswear-inspired loafers in black leather.
Tiny gold hoops and a chain strap shoulder bag finish this ensemble with scholarly panache. It’s perfect for relaxing fireside while debating the latest bestseller – or gossiping over Manhattans.
Cashmere Turtleneck and Pleated Skirt
Exude elegance in a cashmere turtleneck tucked into a pleated midi skirt.
Soft cashmere feels decadent against bare skin – making it ideal for a top you’ll keep on all night long at the bar.
Opt for an off-white ribbed version in a slim fit.
Pair it with a deep charcoal pleated midi skirt in a heat-retaining wool blend. Make sure the skirt includes belt loops you can slide a slim leather belt through to clinch the waist.
This creates a flattering hourglass shape.
Complete the outfit with leather riding boots, a matching wool peacoat, and oversized circle scarf. The monochromatic palette looks rich and puts all the focus on luxurious textures.
Stop by the bar’s charcuterie board on your way to the table – you’ll fit right in!
Tweed Blazer, Button-Up, and Cigarette Pants
Channel 60s mod vibes in a tweed blazer, button-up top, and cigarette pants.
A collared button-up shirt tucked into high-waisted pants is a flattering, vintage-inspired pairing.
Choose a light blue or pink oxford cloth button-up with a point collar.
Layer a tailored boxy tweed blazer on top. In black and white herringbone or menswear plaids, it adds retro flair.
Tuck the button-up into black or camel skinny ankle cigarette pants.
Finish with minimalist loafers or ankle strap flats and a top handle satchel.
A red lip and cat eye sunglasses optional for the full Twiggy effect.
This chic outfit gives you old Hollywood charm for an evening mingling at your favorite speakeasy-style watering hole.
Velvet Blazer, Lace Cami, and Leather Pants
Feel festive and flirty in a velvet blazer, lace cami, and leather pants.
Few fabrics scream holiday spirit like jewel-toned velvet. Look for a single-breasted blazer in a rich shade like emerald, burgundy, or cobalt.
Pair it with a delicate black lace racerback camisole or bustier.
The romantic lace offers beautiful contrast and allows you to show some skin without baring arms. Make sure the cami has adjustable straps for the perfect fit.
On bottom, balance the femininity with matte black leather leggings.
They’ll not only hold in heat but also polish the look. Finish with pointy-toe ankle booties with a block heel for all-night comfort.
No accessories needed for this outfit beyond a black leather clutch.
The textures and colors make a major style statement. Grab a glass of red wine and cozy up in a corner nook to catch up with friends.
Sweater Cape, High-Waisted Jeans, and Ankle Boots
Make a dramatic statement in a hooded sweater cape worn over high-waisted jeans and ankle boots.
Sweater capes are having a major moment, bringing cozy drama to any cold weather outfit. Choose one that hits mid-thigh in a warm neutral like camel, gray, or ivory.
Layer it over black high-waisted skinny jeans – the waist accentuates your curves while the skinny cut elongates your legs.
Pair with black leather ankle boots with a chunky heel for all-night comfort and stability on slick surfaces.
Finish with a circle crossbody bag in a coordinating neutral tone.
You can skip the coat since the cape keeps your torso and arms covered. Just bring mittens along in your bag.
Keep accessories minimal with simple gold hoops, a couple dainty necklaces, and a stack of thin bangle bracelets. Let the sweater cape be the star of the show. Its effortless chic vibe is perfect for grabbing a glass of Malbec at a modern lounge.
You’ll stay toasty while serving up serious style!
Fisherman Sweater and Paperbag Pants
Stay snuggly while looking put-together in a chunky fisherman sweater and paperbag waist pants.
Aran knit fisherman sweaters with Nordic patterns instantly feel warm and rustic – ideal for a log cabin bar vibe.
Go for one in ivory or tan to complement your skin tone.
Pair it with black paperbag pants that nip in at the waist and billow through the legs.
The cropped leg also helps give you a long, lean silhouette. Make sure to add belt loops and pick a thin leather belt in brown or black to match your boots.
Complete the outfit with over-the-knee riding boots and a printed silk scarf.
You’ll be cozy and stylish sipping your old fashioned by the fire or grabbing a game of pool with friends.
The colder months are all about layering luxe textures, warming hues, and strategically baring skin while keeping covered.
Have fun mixing and matching elements to create looks that reflect your personal style.
And don’t forget the finishing accessories like jewelry, handbags, and footwear to pull your outfit together into a chic winter ensemble.
Now you’re ready to head out into the crisp, cold air and cozy up fireside at your favorite local watering hole.
Stay warm and embrace hygge by donning winter outfits that are as fashionable as they are functional.
