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What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy

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When it’s super cold outside but you’d want to go on a date, you might be caught up in a style rut. If you’re wondering what to wear on a winter date, we share cozy date night outfits for winter to look feminine.

While there are plenty of date night outfits you can wear all year round, you can’t take fashion risks during winter or autumn, whether it’s your first date or not.

During such a cold season, layering clothes is your biggest style tip. Having a classy jacket, trench coat or a denim jacket, and more pants including a pair of jeans for a date night is a must.

If your date setting is a fancy restaurant, consider dressing in a pair of trousers or going for a polished dress.

What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
Courtesy: Victoria Fox

Going outside in the winter means donning more chunky sweaters and long coats and lamenting the fact that we can no longer all frolic in the sun. There will be no more summer dates! But that’s fine. It’s not all horrible, though.

Even if you’re outside, winter dates can be entertaining, and most importantly, you can still look chic during your winter dates.

What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
Courtesy: Mia Mia Mine

Whether you’re gearing up for a chilly restaurant date, headed for holiday shopping, going for a wine tasting, or a hot chocolate party, there are night outfits you can wear to look feminine yet cozy in the winter.

Before we share them, here are a few tips to keep in mind when dressing up for a winter date.

Winter Dressing Tips for a Winter Date

When it comes to your winter wardrobe, your priority should be to keep yourself warm. But that doesn’t mean you can’t have fun with your winter style.

Consider these fashion ideas for staying chic while looking great on your winter date:

1. Layer like a Pro!

What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
Courtesy: Rita Tesla

Layering is always on-trend in the winter because this practical way allows you to dress up when it’s really cold. So, don’t be afraid to pile on the layers. However, the key to avoiding ruining your look is to wear three layers.

Silk underwear, a merino wool turtleneck, and leggings that could help keep you warm without making you sweat could be your base layer.

For warmth, a heavier jacket can be used as your middle layer. and the outer layer, such as a winter coat or parka, acts as a wind and rain barrier.

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2. Wear Body-fitting Clothing

What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
Courtesy: Olga Mashko

Wearing body-fitting clothing will help prevent wind chill so swap your wide-leg pants for skinny jeans, which also help visually balance out oversize knit sweaters and chunky boots.

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    Fleece-lined tights or leggings under mini skirts and dresses will also help keep your legs warm.

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    3. Wear Long Coats

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Rita Tesla

    If your aim is to stay warm during your winter date, you need to keep your entire torso covered. Skip the cropped jackets and make sure you have at least one long chunky sweater and coat for the coldest days.

    Style Tips…

    For cold winters, invest in wool. The moisture-wicking wool keeps you warm and dry all day and if you find wool itchy, consider merino (a lightweight wool that’s great as a base layer) and cashmere (a soft wool that will keep you cozy).

    You also want to avoid cotton in the winter. While it is an amazing, and breathable material, it holds a lot of water, making it less ideal for the winter weather.

    So save your plaid flannel shirts, corduroy pants, and sweaters for the fall and spring seasons. Wear wool pants instead of denim if you have them.

    Another tip is to ensure that your clothing is weatherproofed. Before winter, have your favorite winter boots reheeled and weatherized. Also, spray weather-proofing spray on your rain jackets if needed.

    4. Treat your Hat, Gloves, and Scarves as Accessories

    Scarves, hats, and gloves are the best way to keep your whole body warm. A boldly colored cashmere beanie can brighten up a dull winter outfit while adding a hat is also a simple style hack to keep your entire body warm.

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    5. Rock a Good Pair of Boots

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Mia Mia Mine

    A good pair of boots is the key to a great winter style, even for dates.

    Have a great pair of over-the-knee boots? Pair them with a short dress and cute tights to show them off. You can also rock a pair of fantastic ankle boots with a thick knit and skinny jeans.

    If you live in a place with snow, choose shoes with treads to avoid slipping on ice. You can wear them over thick wool socks to prevent frostbite.

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    6. Repurpose Warm-Weather Favorites

    Summer wardrobes are always date-ready! If you don’t like the idea of keeping your summer date night outfits away, repurpose them for your winter dates.

    Here’s how: layer a jacket over your favorite summer dresses or rock a turtleneck underneath, and finish the look with ankle boots for a cute, date-ready winter outfit idea.

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Varlesca.pl

    Flowing skirts and short-sleeve T-shirts aren’t off-limits, as long as you have a solid base layer underneath or atop.

    Style Tip…

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Dilara

    Remember to play with texture and colors. Winter fashion doesn’t have to be boring. Incorporate texture into your look with leather pants, ribbed and cable-knit cardigans, faux fur coats, shearling coats, and quilted puffer coats.

    Also, mix shades of colors to create beautiful monochromatic looks that you can wear on a winter date.

    You May Also Like: How To Wear Monochromatic Outfits & Look Elegant

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy

    Now you’re ready to dress up for your winter date! Try these outfits when you’re looking for what to wear on a winter date:

    1. Rock Oversized Sweater Dresses & Long Boots

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: XPaulinee

    If you’re searching for a chic but also absolutely stylish look to wear on a winter date, opt for an oversized sweater and bring an instant sultry vibe to this ensemble by rocking a pair of dark brown leather boots.

    Mid-calf and long boots pair effortlessly with oversized sweaters as they provide more coverage. And if it’s too cold, don’t hesitate to wear a comfy pair of stockings underneath.

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Mia Mia Mine

    You can also layer a long coat atop for extra warmth, and add a fedora.

    You May Also Like: How To Look Good In Slouchy Over-The-Knee Boots

    2. Leather Pants & Chunky Sweaters

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Lucy Grassso

    If you’re hunting for a comfortable yet absolutely stylish look, wear a chunky sweater and leather leggings. Feel free to layer an oversized blazer or coat atop.

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Lucy Grassso

    For something more on the smart side to complement this outfit, introduce black stilettos to the equation. But if the ground is too wet to wear stilettos, then ankle boots will suffice!

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    3. Long Sweater Dresses & Ankle Boots

    For an outfit that’s super simple but can be modified in a variety of different ways, opt for a midi sweater dress and add a pair of brown or black ankle boots to the mix et voila, the outfit is complete.

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    4. Summer Dresses & Long Boots

    Ladies, you can try your favorite summer dress in the winter then pair it with boots for an ensemble that is super effortless.

    The secret is to layer up and down so you can stay warm- think turtleneck tops underneath or jackets and coats atop.  

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Soitalian.pl
    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Soitalian.pl

    Another useful styling tip to wear your summer dresses in the winter is to finish them with over-the-knee boots. These long boots make your look sophisticated.

    Don’t let the boots overshadow the rest of your outfit, hence no vibrant colors, shiny details, and other unnecessary details for your boots.

    5. Mini Skirts & Long Boots

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: XPaulinee
    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Lucy Grassso

    Don’t overlook the possibility of wearing a miniskirt in winter. This wardrobe staple can be worn with almost anything in your closet and since it reveals much of your skin, it seems hard to style in the winter when it’s cold out.

    However, by adding a few layers to keep yourself warm, you can rock your mini skirt any time of the year to look and feel great.

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: XPaulinee

    Pair with a warm blouse, throw on a blazer or coat before finishing your look with long boots and stockings (optional). Perfect look for a winter date night!

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    Style Tip…

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Dress in Heels

    Before the ground gets too wet in the winter, you can wear your stilettos- black ones should suffice. Kep your legs warmly covered by wearing stockings. This is a great way to continue wearing your minis in the cold months.

    6. Denim Jeans & Layers

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: XPaulinee
    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Lucy Grassso
    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Mia Mia Mine
    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Katerina Themis
    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Katerina Themis

    If you would like to take your casual look in denim jeans to a new level so you can wear this ensemble on a winter date night, marry an oversized blazer, long cardigan, or long coat with skinny jeans.

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Charlie Kamale

    If you’re not sure how to finish off, a pair of pointed-toe booties, whether ankle or knee-high, is a safe option.

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    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Dilara

    For an outfit that’s very straightforward but can be manipulated in a myriad of different ways, pair a tan knit oversized sweater with skinny jeans. Avoid looking too casual by finishing off with a pair of black leather mid-calf boots and a gorgeous bag.

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    7. Long Ribbed Dresses

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Luba
    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Amara.nsl
    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Victoria Fox
    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Rita Tesla

    Long ribbed dresses are perfect for winter date nights. You can wear these dresses and be stylish even in the cold. Master the effortlessly stylish look by opting for a sweater dress and pair this outfit with a matching overcoat and pointed-toe boots.

    If you like, you can wear it with heels too.

    Style Tip…

    Sweater dresses offer an effortless kind of polish but sometimes, you need an edgier winter date night look. That’s where your white evening dress comes in.

    Just remember to bring along a warm fur coat when it gets too cold at night.

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    8. Shorts & Fur Coats

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Alena Alena

    This pairing of a fur coat and leather shorts is indisputable proof that a pared-down casual getup can be worn for a winter date night. A pair of ankle boots instantly steps up the style factor of any ensemble.

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    9. Long Blazers & Midi Skirts

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Twota
    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Twota
    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Twota

    When the date night situation calls for a classy yet cool look, you can opt for a classy blouse and a slip or pleated midi skirt. Now, try teaming a long or oversized blazer with this look.

    As for footwear, complete your outfit with leather ankle boots or black leather heeled sandals to pull the look together.

    10. Jumpsuits & Trench Coats

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Signed Blake

    Breathe personality into your winter date wardrobe with a jumpsuit in your preferred color choice.

    Reach for a long trench coat to achieve a current winter date outfit. Add a dash of sultry refinement to this getup with leather heeled sandals.

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Luba

    Jumpsuits are winter-perfect but you can also go for a two-piece pants set. And if you want to effortlessly dial up this look, why not add a long white winter coat and pointed-toe leather boots to the equation?

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    11. Blazer Dresses & Boots

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Amara.nsl

    Make a blazer dress your outfit choice to put together an interesting and modern-looking winter date outfit. A pair of long black leather boots instantly rev up the glamour factor of this look.

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    12. Dressy Pants & Long Coats

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Victoria Fox
    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Victoria Fox
    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Victoria Fox
    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Victoria Fox
    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Victoria Fox

    Putting together a long winter coat and dress pants is a fail-safe way to inject your day-to-day styling collection with some glamour.

    If you need to easily dress up this look so it’s winter-date-ready, add bold accessories like beret hats, leather bags, and jewelry to the equation.

    The secret is to wear a monochromatic ensemble or color block with solid outfit colors to ensure your look is not just cosy enough but also cohesive and interesting.

    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Victoria Fox
    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Rita Tesla
    What To Wear On A Winter Date: Night Outfits To Look Feminine Yet Cozy
    Courtesy: Mia Mia Mine
    Try These Casual Date Outfits For Fall To Look Chic
    Courtesy: Gabrielegz
    Try These Casual Date Outfits For Fall To Look Chic
    Courtesy: Lucy Grassso

    Now, finish with a pair of stilettos or booties, and head on to your date!

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    Never be caught up in a style rut wondering what to wear on a winter date! Try these night outfit ideas to look feminine yet super cozy!

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