8 Winter Date Night Hairstyles
- Joao Nsita
- Oct 7
- 14 min read
Winter, with its crisp air and early, starlit evenings, possesses a romance all its own. It’s a season that invites intimacy, encouraging us to seek warmth and connection, often over a candlelit dinner or cozied up by a fireplace. A winter date night feels inherently special, a little pocket of warmth and glamour in the midst of the cold. And when it comes to crafting the perfect look for these occasions, your hairstyle is the ultimate finishing touch. It’s the element that can transform your outfit, elevate your confidence, and perfectly capture the magical, romantic spirit of the season.
As we look towards the winter 2025-2026 season, the trends emerging from the visual mood boards of Pinterest and TikTok are a beautiful celebration of effortless elegance. The era of stiff, overly complicated updos is over. In its place is a movement towards "soft glamour," a focus on touchable textures, romantic details, and hairstyles that look polished but never feel overworked. The "coquette" and "balletcore" aesthetics continue their reign, bringing with them a profusion of luxurious velvet ribbons, satin bows, and delicate pearls. The goal is to create a look that is both incredibly chic and comfortably wearable—a style that can withstand a beanie on the way to the restaurant and still look perfect when you arrive. This list is your definitive guide to the eight most romantic and on-trend winter date night hairstyles, presented in descending order.
We hope you find this article inspiring and helpful for your winter styling! If you enjoy our content, please consider supporting our work with a small donation or by sharing our articles with your friends and family. Your support helps us continue to create joyful and informative content.
8. The Embellished Headband Wave
The Vibe: Instantly glamorous, effortlessly chic, and perfect for a last-minute date night. This is the ultimate accessory-as-the-style hack.
Detailed Description: This look is a masterclass in the power of a single, show-stopping accessory. It takes a simple, classic hairstyle—soft, touchable waves—and instantly elevates it to a sophisticated, party-ready look with the addition of a beautiful, embellished headband. The trend for statement headbands is massive, and for a winter date night, they feel particularly special. Think plush, deep-toned velvet for a touch of cozy luxury, classic pearls for a timeless, elegant feel, or glittering crystals for a dose of festive glamour. It’s a versatile look that works on all hair lengths, from a chic bob to long, flowing locks, and it requires almost zero styling skill to execute beautifully.
How to Achieve the Look: The key to making this look feel modern and romantic is to create a soft, natural-looking wave, not a tight, perfect curl.
Create the Waves: Start by applying a heat protectant spray. Using a large-barrel curling iron or a wand, curl one- to two-inch sections of your hair, alternating the direction of each curl to create a more natural, less uniform look. For an even more "undone" feel, leave the last inch of your hair straight.
Soften the Look: Once your hair has cooled, gently run your fingers through the waves to break them up and soften them. You can add a spritz of light-hold hairspray or a texturizing spray to give the waves a bit of grit and staying power.
Add the Headband: Simply place your chosen statement headband on your head, positioning it about an inch or two back from your hairline. You can pull out a few soft, face-framing tendrils to complete the romantic, effortless vibe. This style is proof that you don’t need to spend hours on your hair to create a look that is both incredibly chic and perfectly appropriate for a romantic evening. The simple elegance of this look is timeless, a quality shared by some of the best holiday rom-coms.
You can find a stunning array of statement headbands, from simple velvet to intricate, beaded designs, on platforms like Etsy or at retailers like Anthropologie.
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7. The Sleek, High-Shine Ponytail with a Twist
The Vibe: Modern, powerful, and undeniably sexy. This is a look that is both incredibly chic and fiercely confident.
Detailed Description: This is not your everyday gym ponytail; this is a deliberate, polished, and perfectly executed statement style. The beauty of the sleek ponytail lies in its minimalist perfection—the ultra-smooth, glass-like finish of the hair and the clean, sharp lines. For a winter date night, you can elevate this classic look with a simple twist—literally. By wrapping a strand of your own hair or a beautiful piece of velvet or leather around the base of the ponytail, you transform it from a simple style into a sophisticated, high-fashion look. It’s a perfect choice for a night out in the city, a style that gets your hair off your neck to showcase a beautiful pair of earrings or the collar of a chic coat.
How to Achieve the Look:
The Foundation is Smoothness: This style requires a perfectly smooth base. Start by applying a heat protectant and a smoothing cream to damp hair. Blow-dry your hair straight, using a boar bristle brush to create tension and shine. Follow up with a flat iron, working in small sections to get the hair as sleek and straight as possible.
Create the Ponytail: Using a boar bristle brush to eliminate any bumps, brush your hair back into a tight ponytail. You can position it high on the head for a dramatic, face-lifting effect, or low at the nape of your neck for a more subdued, elegant feel. Secure it with a strong hair tie.
The Twist: Take a small, half-inch section of hair from the underside of the ponytail. Wrap this section tightly around the hair tie to conceal it, and secure the end by tucking it into the hair tie or using a bobby pin.
The Finishing Touch: Finish the entire style with a generous spritz of a high-shine spray to achieve that coveted "liquid hair" look. This is a look that commands attention, much like the iconic characters from the best TV comedies of the 2010s.
External Link: For tutorials on how to achieve the perfect sleek ponytail and other celebrity-inspired looks, celebrity hairstylist Chris Appleton's Instagram is a fantastic resource.
We hope you found this style inspiring! If you enjoy our content, please consider supporting our work with a small donation or by sharing our articles with your friends and family. Your support helps us continue to create joyful and informative content.
6. The "Balletcore" Braided Bun
The Vibe: Elegant, polished, and incredibly romantic. The "Balletcore" aesthetic, with its celebration of the graceful style of ballet dancers, is a massive trend, and this hairstyle is its perfect, sophisticated expression.
Detailed Description: This is the ultimate elegant updo for a formal winter date night, like a trip to the ballet or a fancy holiday party. It takes the classic, sleek chignon and adds a beautiful, intricate detail with the addition of a simple braid. It’s a style that is incredibly secure and will stay perfectly in place all night long. It keeps your hair completely off your neck, making it ideal for wearing with high-collared dresses, turtlenecks, or statement jewelry. It’s a look that is pure, understated elegance, a testament to the idea that sometimes the most beautiful styles are the most classic.
How to Achieve the Look:
Start with a Sleek Ponytail: For a polished look, start by brushing your hair back into a smooth, tight ponytail. A low ponytail at the nape of the neck is classic and elegant, while a high ponytail will give you a more dramatic, top-knot effect.
Braid and Wrap: Braid the ponytail into a simple, three-strand braid and secure the end with a small, clear elastic. Then, gently wrap the braid around the base of the ponytail to form a bun.
Secure It: Tuck the end of the braid underneath the bun and secure it tightly with bobby pins. For extra hold, you can spritz the bun with a firm-hold hairspray. For an even softer, more romantic look, you can gently pull on the edges of the braided bun to loosen it slightly and pull out a few delicate, face-framing tendrils. This kind of timeless elegance is a quality shared by some of the greatest HBO dramas of all time.
External Link: You can find beautiful, minimalist hair accessories, like elegant pins to adorn your bun, at retailers like J.Crew.
We hope you found this style inspiring! If you enjoy our content, please consider supporting our work with a small donation or by sharing our articles with your friends and family. Your support helps us continue to create joyful and informative content.
5. The Romantic "Coquette" Half-Up Bow
The Vibe: Feminine, dreamy, and perfectly on-trend. The "coquette" aesthetic is all about embracing a soft, romantic, and slightly vintage femininity, and the bow is its ultimate symbol.
Detailed Description: The half-up, half-down hairstyle is a date night staple for a reason: it’s the perfect balance of polished and relaxed. It keeps the hair out of your face while still showing off your length. The 2025 version of this classic style is all about the accessory. A simple, beautiful bow, tied around the half-ponytail, instantly transforms the look from everyday-pretty to special-occasion-romantic. It’s a sweet, charming, and incredibly stylish look that is both incredibly easy to achieve and perfectly on-trend.
How to Achieve the Look:
Create a Soft Base: This style looks best with a bit of texture in the hair. Start by creating soft, loose waves with a curling iron or by enhancing your natural texture with a curl cream.
The Half-Up: Section off the top half of your hair, from your temples to your crown. You can use a brush for a more polished look, or just use your fingers for a more relaxed, undone feel. Gather this section into a small ponytail at the back of your head and secure it with a clear elastic.
The Bow: This is where the magic happens. Take a length of your chosen ribbon and simply tie it in a bow over the elastic. For a winter date night, a plush velvet ribbon in a deep jewel tone like burgundy or emerald green is a stunning choice. A classic silk or satin ribbon in black or ivory is also incredibly chic. You can leave the tails of the bow long for a more dramatic, romantic effect. This is a look that feels both sweet and sophisticated, a perfect match for a romantic evening. For more on creating romantic moments, check out these 10 fall romances set in pumpkin patches & cafés.
External Link: For an incredible selection of high-quality, beautiful ribbons in every colour and texture imaginable, the website May Arts Ribbon is a fantastic resource for crafters and stylists.
We hope you found this style inspiring! If you enjoy our content, please consider supporting our work with a small donation or by sharing our articles with your friends and family. Your support helps us continue to create joyful and informative content.
4. The Hollywood Wave Side Sweep
The Vibe: Pure, unadulterated, red-carpet glamour. This is a timeless, show-stopping look for a truly special occasion.
Detailed Description: The classic Hollywood wave is the epitome of vintage glamour. It’s a highly polished and structured style where all the hair is set in a uniform, S-shaped wave pattern. The deep side part and the way the hair is swept over one shoulder create a look that is both incredibly romantic and powerfully glamorous. While the traditional, pin-set version is very time-consuming, a modern, more achievable version can be created at home with a curling iron and the right technique. It’s a look that is guaranteed to make you feel like a movie star.
How to Achieve the Look:
The Deep Side Part: Start by creating a clean, deep side part.
The Curl: This is the most crucial step. Using a 1- to 1.5-inch curling iron, curl one- to two-inch sections of your hair all in the same direction. This is what will create the uniform wave pattern. After you release each curl, you can either clip it up to cool to create a stronger set, or gently let it fall.
The Brush-Out: Once all of your hair is curled and has completely cooled, this is where the magic happens. Take a boar bristle brush and gently begin to brush through your curls. Don't be afraid! The curls will start to relax and meld together, forming that classic, cohesive wave shape.
The Sweep: Use a light-hold hairspray to tame any flyaways and to help the waves hold their shape. Gently sweep all of your hair over one shoulder and secure it at the back of your neck with a few bobby pins if needed. This is a look of pure, timeless elegance, a quality shared by the best Eddie Murphy movies.
3. The "Fluffy" 90s Updo
The Vibe: A perfect blend of polished and effortlessly undone, inspired by the iconic supermodel updos of the 90s.
Detailed Description: The "fluffy" updo has become the go-to "cool girl" hairstyle of the 2020s, and it’s a perfect choice for a winter date night. It’s a softer, more romantic take on the classic top knot or chignon. The key to the look is its airy, voluminous texture and the two face-framing tendrils that are left out at the front. This gives the style a relaxed, slightly nostalgic, and incredibly flattering feel. It’s a look that says, "I just effortlessly threw my hair up," even though the result is incredibly chic and intentional.
How to Achieve the Look:
Create Texture: This style works best on hair that has a bit of grit and texture. Start by spritzing your hair with a texturizing spray or a dry shampoo.
Section Out the Tendrils: Before you pull your hair up, use a comb to section out two thin, face-framing pieces at the front.
The Fluffy Bun: Gather the rest of your hair into a ponytail at your desired height (a mid-height ponytail at the back of the head is classic for this look). On the final pull-through of your elastic, only pull the hair halfway through to create a looped bun, leaving the ends out. Then, take the looped bun and the loose ends and arrange them into a soft, voluminous shape, using bobby pins to secure it. The key is to not make it too perfect; pull and tug at the bun to create that "fluffy," airy texture.
Finish the Tendrils: Use a small curling iron or a flat iron to add a gentle, face-framing bend to your two tendrils. This 90s-inspired look is pure nostalgia, a feeling we also get from these 20 Of The Best Songs From Oasis.
2. The Braided Headband Updo
The Vibe: Romantic, bohemian, and beautifully intricate-looking (but secretly easy!).
Detailed Description: This is a stunning updo that creates the illusion of a braided headband using your own hair. It’s a beautiful and practical style that keeps all of your hair up and out of the way, making it perfect for a cozy dinner or a night of dancing. The braided detail at the front adds a touch of romantic, fairytale-like elegance, and it’s a style that works beautifully on a variety of hair lengths.
How to Achieve the Look:
Create Two Braids: Part your hair where you normally would. Take a two-inch section of hair from right behind your ear on one side and create a simple, three-strand braid, securing the end with a small, clear elastic. Repeat on the other side.
The Headband: Take one of the braids, bring it up and over the top of your head like a headband, and secure it behind the opposite ear with a bobby pin. Do the same with the other braid, laying it just behind the first one.
The Updo: Now you have two options. For a simple half-up look, you can leave the rest of your hair down. For a full updo, gather the remaining hair at the back of your head and twist it into a loose, messy bun, securing it with bobby pins. This is a beautiful and versatile style, a perfect choice for one of these dreamy winter wedding themes.
External Link: The beauty publication Byrdie has many fantastic tutorials and visual guides for braided updos like this one.
1. The Velvet Ribbon-Tied Low Ponytail (Reprise at #1)
The Vibe: Timeless, minimalist, and the epitome of understated romance. Taking the top spot on our list is a style that is both the simplest and, arguably, the most chic.
Detailed Description: The velvet ribbon-tied low ponytail is the perfect embodiment of the "soft glamour" and "coquette" trends. It takes the most simple, classic hairstyle—a low ponytail—and transforms it into a high-fashion statement with the addition of a single, beautiful piece of velvet ribbon. The plush, luxurious texture of the velvet instantly adds a festive, wintry feel, while the simple, clean lines of the ponytail keep the look modern and sophisticated. It is a look of pure, effortless elegance.
How to Achieve the Look:
The Perfect Ponytail: The key to this look is to start with healthy, shiny hair. You can wear your hair straight and sleek for a more modern feel, or with soft, brushed-out waves for a more romantic look. Gather your hair into a low ponytail at the nape of your neck and secure it with a clear or hair-coloured elastic.
The Ribbon: This is where the magic happens. Take a long, thick velvet ribbon and simply tie it in a beautiful, classic bow over the elastic, allowing the ends to hang down. The quality of the ribbon is what makes this look so special. For a holiday date night, a deep, jewel-toned velvet—like burgundy, emerald, or sapphire—is absolutely stunning. A classic black velvet ribbon is also incredibly chic and versatile. It’s a five-second style upgrade that makes a simple hairstyle look incredibly intentional, sophisticated, and deeply romantic. It is proof that sometimes, the most beautiful statements are the quietest ones. This simple, elegant style is as timeless as a classic Gilmore Girls episode.
External Link: You can find beautiful, high-quality velvet ribbons in a huge array of colors on Etsy, which is perfect for supporting small businesses.
Conclusion
A winter date night is an opportunity to embrace the romance and the magic of the season. The eight hairstyles on this list are a testament to the power of effortless elegance, proof that you don’t need to be a professional stylist to create a look that is beautiful, festive, and completely you. Whether you choose a simple, ribbon-adorned ponytail or a glamorous Hollywood wave, the most important element of any hairstyle is the confidence it gives you. So, this winter, have fun with your hair, embrace the cozy glamour of the season, and create a look that makes you feel as special as the night ahead.
We hope you found this article inspiring and helpful! If you enjoy our content, please consider supporting our work with a small donation or by sharing our articles with your friends and family. Your support helps us continue to create joyful and informative content.
For more on finding the perfect look for any occasion, check out these other articles from That Love Podcast:
FAQs
What's the best way to make my hairstyle last all night? The key is in the prep. Start with a good foundation, like a texturizing spray or a mousse, to give your hair some grip. After you've styled your hair, finish with a light but firm-hold hairspray. For updos, use high-quality bobby pins that match your hair color.
I have very fine hair. How can I add volume to these styles? Start by using a volumizing mousse at your roots before you blow-dry. Dry shampoo is also a fantastic tool for adding grit and volume to fine hair, even when it's clean. For styles like the fluffy bun, gently backcombing the ponytail before you create the bun can add a lot of extra fullness.
I'm not very good at styling my hair. Which of these looks is the absolute easiest? The Embellished Headband Wave and the Velvet Ribbon-Tied Low Ponytail are the two easiest styles. They rely on a beautiful accessory to do all the heavy lifting and require very minimal styling skills.
What are "face-framing tendrils"? These are the two thin sections of hair that are intentionally left out at the front of an updo to soften the look and frame the face. This was a massive trend in the 90s and has made a huge comeback.
How do I choose the right holiday hair accessory? Think about your outfit. If your dress is very sparkly and ornate, you might want to choose a simpler accessory, like a classic velvet bow. If your outfit is more minimalist, you can go for a bold, statement-making accessory, like a crystal-embellished headband.
Can these styles be done on curly hair? Absolutely! Many of these styles are beautiful on natural curls. The half-up style with a bow looks stunning with voluminous curls, and a sleek, high-shine ponytail (using a good gel and brush) can be a beautiful way to showcase the texture of your hair.
What's the best way to get a "high-shine" finish? Start with a shine-enhancing shampoo and conditioner. Use a smoothing serum before you style, and finish with a lightweight shine spray or a glossing mist.
How do I prevent my hair from getting static in the winter? Winter air is very dry, which causes static. Using a moisturizing hair mask once a week can help. You can also keep a small bottle of leave-in conditioner or a dryer sheet in your bag to quickly tame static on the go.
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