25 + First Date Winter Outfits
Going on a first date is always a mix of excitement, a bit of nerves, and the hope of meeting someone special! And let’s be honest, making a great first impression!
That’s why choosing the right winter outfit can make all the difference!
The perfect winter outfit can boost your confidence, make you feel amazing, and help you shine on your next first date.
The last thing you want is to be uncomfortable & shivering from the cold. Wearing the wrong outfit can leave you feeling flustered and possibly even ruin the date (okay, maybe that’s a little dramatic, but you get the idea!).
So, what’s the secret to nailing a winter first date outfit?
The secret to finding the right outfit for a first date is something that’s not only cozy but also flirty and fun!
When you find the right winter date outfit, you don’t have to worry about feeling out of place or uncomfortable. You’ll be able to relax, be yourself, and radiate confidence all night long.
Winter in different locations
Winter looks different depending on where you live. Some places are freezing cold with snow and ice, while others are more mild and sunny with temperatures in the 60s.
This article will give you flirty and fun winter outfit ideas for a first date, no matter your location.
If you live somewhere colder, you can adapt the outfit with more layers, and if you’re in a warmer climate, you can skip the extra layers for a more casual look.
Simply add more layers to any of these looks if you need extra warmth, or remove a few if it’s on the warmer side.
For a dress, layer with fleece tights and boots. You can always throw on a vest over your sweater and another jacket on top. Don't forget winter accessories like gloves and scarves!
It's all about balancing good style and warmth. The outfit you want to wear on your next first date should keep you cozy, but also make a great first impression!
Even though it can feel a little daunting, don't worry- Ive got you covered. Below are some beautiful and effortless outfits ideas you can simply copy.
Let's dive into some cute outfit ideas perfect for a firsts date in winter
25+ First Date Winter Outfits
Floral dress with sherpa coat and knee high boots
Coat: This stylish and cozy Shrouded in Sherpa Coat is perfect for chilly days. It's crafted from a substantial sherpa fleece and has a collared neckline, dropped shoulder for a relaxed fit, and button flap side seam pockets for practical storage. The button front closure makes it easy to wear. Add a touch of warmth to your wardrobe whenever you need it!
Wear something red hot
Rock a unique and playful look with our I'll Never Forget Ribbed Dolman Sleeve Top. This red top features a ribbed knit with raw edge details, drop shoulder, and banded hemline for a comfy fit. Perfect for any casual date night, this top will make sure you're one to remember!
Get a little edgy in a cropped leather jacket
Get your 80's vintage vibe on with this 'Greece Lighting' inspired vegan leather crop jacket. This sleek jacket features a functional zipper and front pockets, a high collar and full lining. A Perfect jacket for a first date night - if an edgier playful look is your thing!
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Stay chic in a sweater Dress
A dreamy and cozy sweater dress is a perfect first date outfit for winter! It's cozy, chic and easy to dress up or down. Style a sweater dress with knee high boots and layer over a gorgeous coat for an unforgettable evening!
What to wear on a first date in winter?
Pick cozy layers that keep you warm and show your style.
Wear a long sleeve dress with fleece tights and boots. Add an extra layer with an overcoat, gloves and a scarf.
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Velvet Dress & Stilettos
How to dress seductive in winter?
Go for fitted pieces that show your shape under warm layers. A form-fitting sweater dress with tall boots can be sexy yet cozy.
I love a mini skirt with fleece leggings and a fitted sweater knit top. Something cozy and cute, yet easy to add extra layers over like a long jacket or blazer.
You can also try colors like deep reds or black. Wear lace or silky fabrics to feel extra flirty.
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Red maxi dress & booties
Perfect for a first date - Fall in love with this ruffle overlap V neck woven midi dress with a shirred waist and long elastic bubble sleeves. With a fit and flare design, wide ruffle hem and side pockets, prepare to look gorgeous in this festive maxi.
Is it ok to wear red on a first date?
Yes, red can be great for a first date!
It shows confidence and passion. Just don't overdo it. A red sweater or dress can make you stand out. Pair it with neutral colors to balance the look.
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Mini skirt with a chunky knit sweater
Nothing says flirty like a sweet mini skirt! And pairing a mini skirt with a chunky knit sweater keeps you cozy and flirty. Layer with a pair of fleece tights to stay warm and complete the look with Mary Jane flats! Add an overcoat to beat the winter chill!
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Jacquard Sweater dress wrapped in a waist belt & booties
Romantic and elegant, this dreamy Jacquard sweater dress is perfect for any first date in winter! Throw on some fleece tights and an overcoat and you are ready for an incredible time!
How do I dress romantic in winter?
Soft textures and feminine details create a romantic vibe. Try a skirt with a cozy sweater and tights. Add dainty jewelry and a long coat in a pretty color can also set a romantic mood.
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Be edgy and sweet in a knit top & mini skort
This look is flirty with a little bit of edge! Rock a gorgeous skort with a sweater knit top for a combo of cozy and flirty. Stay warm by layering black tights and a jacket.
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Be Feminine in a lace cardigan and a midi skirt
For a romantic and flirty look, go for a ribbon lace cardigan and pair it with a midi skirt. Complete your look with booties and sheer tights to stay warm on your next first date in winter.
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Wear a red babydoll with jeans and boots
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Wear a long sleeve plaid red dress
You will lovethis plaid elastic V neck flutter sleeve maxi featuring a flattering fit and flare design, ruffle long sleeves and smocking. Stylish and versatile, this holiday ready maxi with a back button clasp is perfect for all your festivities.
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Wear a tunic top with a vest and knee high boots
Indulge in comfort and style with our You're Too Kind Waffle Knit Top. The soft waffle knit fabric and scoop neckline provide ultimate comfort, while the exaggerated contrast sleeve cuff and asymmetrical hemline add a touch of quirkiness. Side slits allow for easy movement, making this top the perfect blend of fashion and function.
What to wear on a night out when it's so cold?
Layer a cute top under a chic vest and add a jacket. Pair it with jeans and knee high boots to stay warm.
Knee-high boots keep your legs toasty. Don't forget a stylish blanket scarf and gloves to stay cozy all night.
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Wear a silky blouse and kitten heels
Add a touch of playful elegance to your wardrobe with our Pretty in Pink Satin Puff Sleeve Blouse. Made of luxurious poly satin, this blouse features puff sleeves with banded sleeve cuffs for a unique and stylish look. The back button keyhole closure adds a touch of charm, making this blouse perfect for any first date.
How to wear jeans on a first date in winter?
Grab your favorite jeans and add warm layers on top. Go for a polished look by styling a chic sickly blouse or a cozy knit sweater.
Ankle boots or kitten heels work well with jeans. Add a statement coat to dress up the look and accessories with a pair of dainty sparkling earrings.
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Wear a V neck maxi dress
You will love this plaid elastic V neck flutter sleeve maxi featuring a flattering tiered ruffle hemline. Stylish and versatile, this stylish maxi is perfect for all your holiday festivities.
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Wear a red velvet dress
Perfect for catching second glances, this velvet red dress is perfect for a first date! Made with velvet fabric and side pockets, this dress offers multiple winter trends with a mock neck, smocked long bubble sleeves and a smocked waist. Simple elegance that can be worn for years to come!
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Wear a silky smooth maxi dress
For a walking date, wear a romantic maxi dress and pair it with your best pair of sneakers. Your feet will thank you later and you'll still feel flirty and sweet in a dress!
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Wear a mini velvet dress and black tights
Look and feel your best this season with our Tied In A Bow Velvet Dress! This luxurious velvet dress has a flattering mock neckline, sleeveless design, cased elastic waistband, and comes with a removable self-tie belt and ruffled hem for a chic, sophisticated look.
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Try a bodycon dress with a cozy cardigan
You will definitely fall in love with our Sure To Fall In Love Bodycon Dress! A stretchy, poly spandex blend hugs your curves in all the right places, shaping a round neckline with three quarter sleeves and a midi-length hem. Pair with a blazer and heels for a chic date night look!
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Wear a golden dress with heels
Look and feel your best in our Magnificent Muse Velvet Dress. Crafted from crushed velvet with a V-neck, long bishop sleeves, and a wide ruffled hemline, it will flatter your figure and make a statement.
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Be chic on a first date in blush and a blazer
Rock your individuality in our It's For the Aesthetic Ballon Sleeve Dress! Fashioned from a poly satin plisse material, this adorable frock boasts a cased elastic shoulder and waist, along with a fun scoop neckline and optional off-shoulder cut. The balloon sleeves and cased elastic cuffs give a touch of playful charm to this dress, while the lined skirt keeps you covered.
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Go Gorgeous in Green
Wearing green can make you seem down to earth, a perfect shade for a first date! Dress to impress in our Starlit Glow V-Neck Tiered Dress! Made from dot poly chiffon, it features a flattering v-neckline, playful balloon sleeves with cased elastic cuffs, and a surplice bodice. The tiered and ruffle details add a unique touch, while the lined skirt and bodice ensure comfort.
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Be comfy & Casual with a ribbed top and flares
Going on a casual first date? Like a walk around a park or a casual day out. Spice up your wardrobe with our Better Than Usual Floral Detail Top! Made of ribbed and jersey knit, this top offers high stretch for a comfortable fit. Complete with a round neckline, banded hemline, and exaggerated sleeve cuff, it's perfect for any occasion.
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Wear a red babydoll blouse and wide leg jeans
The flattering V-neckline is framed by playful flutter sleeves, adding a touch of whimsy to your look. The peplum silhouette creates a graceful, feminine shape, while the ruffle details provide a charming finishing touch. Perfect for both casual outings and more polished occasions, this top brings a blend of comfort and style to any wardrobe.
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Layer up in lovely lace
Elevate your layering game with our Lace Layering Top. This elegant piece combines the delicate allure of lace with the practicality of a versatile tank. Featuring a sophisticated boat neckline and a faux wrap design, it offers a chic, flattering silhouette. Perfect for layering under your favorite Tees or sleeveless tops, this top adds a hint of romance and refinement to any outfit. Whether dressing up or down, you'll never be sorry for choosing this timeless layering essential.
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Be stylish & flirty in tweed
The snappy Number Five Tweed Jacket is sure to be the life of the party! Its lightweight tweed and raw edge details provide a stylish look. Plus, its peplum style and faux pearl buttons add the perfect touch of chic. So, slip into this chic jacket and turn heads at your next outdoor gathering!
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Be luxe & lovely in a velveteen blouse
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Wear a little red dress
This Regal Radiance Velvet Dress is timeless elegance in soft velvet. With its V-neck and bubble sleeves, this dress is perfect for any special occasion. Let its luxurious texture take you from day to night looking effortlessly chic.
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Wear a fitted sweater
This Be Still V-Neck Striped Sweater effortlessly combines style and comfort. The slim fit flatters your figure, while the ribbed knit adds texture and warmth. The scalloped neckline and sleeves add a unique touch, perfect for any occasion. The classic stripe pattern adds a timeless, versatile look to your wardrobe.
Conclusion
Choose an outfit that makes you feel good. When you feel good in what you're wearing, it shows. Your date will be impressed by your style and your warm personality shining through.
Looking for more outfit ideas? Check out my boutique for the latest styles HERE
Written by Caroline Flowers
