If you’re heading out on a date night with your other half or a new date, or for an evening out with friends, you want to make sure you look good.

You’ll want to plan your date night out to make sure that you look good, feel good and make the most impact. But, it can be tricky to combine just the right amount of va-va-voom and showing a bit of skin with the practicalities of wrapping up against the elements. That’s why we will give you ideas for the best winter date night outfits that are both warm and stylish.

What to consider when putting together your winter date night outfits

It might actually be easier than during summer

The first thing to do is to embrace winter dressing. It is easier to cover up the parts of your body you aren’t so keen on and show off what you do like. For example, you’re more likely to wear sleeves to cover up upper arms, long flattering layers or black, leg-slimming tights when the weather is cooler.

Don’t forgo comfort

Winter date night outfits - Julie in a wrap dress and boots | 40plusstyle.com

If you feel cold and uncomfortable, you aren’t going to enjoy your date. So, keep your legs warm in a pair of opaque tights, and make sure you incorporate layers that you can wear indoors.

Julie above (read her style interview here) wears a wrap dress with a pair of booties. If you think you’ll be chilly, you can add a pair of tights or leggings.

Recreate her outfit with this similar wrap dress, boots, bag, earrings and sunglasses.

Wear a heel

Winter date night outfits - Boma in heels and leather pants | 40plusstyle.com

If you love the look of heels but find them uncomfortable, date night could be the perfect time to wear them, if you’re heading out for a meal and will be sitting for most of the evening.

Boma @mrs.gaf above wears heeled pumps with her leather pants.

Check out this similar peplum top, coat, leather pants, pumps, handbag and sunglasses.

Opt for sumptuous fabrics for your winter date night outfits

Winter date night outfits - Nikki in a silk shirt and jeans | 40plusstyle.com

Winter is a great time to think about the fabric you’re wearing and ensure it is tactile for date night. Think about silks, satins, velvet or faux fur.

Nikki @40notfrumpy above opts for a silk shirt with her jeans and boots.

Steal her look for your winter day night outfits with this similar silk shirt, wide leg jeans, boots, bag and necklace.

Winter date night outfits ideas

Now, let’s take a look at some winter date night outfits incorporating some of the clothes you’re likely to have in your closet.

midi dress and a jacket

Midi dresses are particularly on trend right now. Add a pair of tights and wear with tall boots to ensure you look fabulous and stay warm.

Midi dress and jacket outfit | 40plusstyle.com

Karen Millen military jacketChelsea28 cuffed midi dressDREAM PAIRS thigh high bootsZadig & Voltaire suede clutchKarine Sultan pendant ear jackets

a figure flattering dress and warm coat

A ruched dress will always be figure flattering. Look out for a coat that sits below the hemline of your dress.

Ruched dress and long coat | 40plusstyle.com

Nordstrom wool & cashmere double face coatKaren Kane faux wrap dressDREAM PAIRS thigh high bootsALDO clutchSilvershake teardrop earringsAcotavie silk scarf

blazer with jeans and long boots

Winter date night outfits to make sure you look good and stay warm | 40plusstyle.com

It’s a good idea to ensure that you can comfortably leave your outerwear on if you want to when you get indoors, so a blazer is a great option.

Angela @angelamashelle above keeps her look neutral and wears her blazer over her shoulders.

Get her look with this similar top, blazer, jeans, over the knee boots, handbag and earrings.

Blazer and jeans | 40plusstyle.com

Eliza J velvet blazerHalogen cross front satin topReformation skinny jeansDREAM PAIRS thigh high bootsZadig & Voltaire suede clutchNordstrom oval earrings

A skirt and sweater and a pop of red lipstick

Wearing a formal skirt with a cozy sweater has been a trend for a few seasons, and definitely isn’t going anywhere this winter. Opt for an off-the-shoulder style for some subtle sex appeal, and wear a long coat so you stay warm getting to your date venue.

Sweater and skirt outfit | 40plusstyle.com

Ted Baker London wool coatM.M.LaFleur off the shoulder sweaterTed Baker London handkerchief hem skirtDREAM PAIRS thigh high bootsALDO clutchNordstrom oval earringsMaybelline New York Color Sensational Made for All lipstick

A long cozy cardigan 

A long cardigan can be perfect for adding warmth and for creating long, lean lines which can have a slimming effect. The bold red, white and black of the outfit below will definitely make a statement.

Long cardigan and leather pants | 40plusstyle.com

Ted Baker London longline jacquard knit cardiganBoden silk shirtKaren Millen leather dipped trousersDREAM PAIRS pumpZadig & Voltaire suede clutchCanvas Jewelry layered necklace

A print dress and neutral accessories 

You don’t have to opt for a bold color when it comes to your winter date night. You could choose an eye-catching print instead and choose a neutral coat, shoes and accessories.

Printed dress and cream coat | 40plusstyle.com

Karen Millen wool cashmere belted maxi coatTed Baker London printed shirt dressIDIFU ankle bootNo Nonsense opaque control-top tightsZadig & Voltaire suede clutchKarine Sultan pendant ear jackets

Turtleneck dress to keep your neck warm

Winter date night outfits - Beth in a sweater dress | 40plusstyle.com

A turtleneck style is an ideal option for winter to ensure you stay cozy.

Beth @styleatacertainage above (read her style interview here) opts for a sweater dress and a long coat.

Check out this similar turtleneck dress, long cardigan, tights, boots, handbag, long necklace and sunglasses.

Turtle neck dress outfit | 40plusstyle.com

Karen Millen notch neck coatNordstrom pleat shift dressNine West pumpThe Drop small toteSilvershake teardrop earring

faux Fur and wide leg pants/jumpsuit

Rather than a dress, if you prefer to wear pants, you could choose a jumpsuit. To keep your shoulders warm and add extra glamour, look out for a cozy wrap.

Jumpsuit and faux fur wrap | 40plusstyle.com

Caracilia faux fur stoleBlack Halo jumpsuitDREAM PAIRS pumpZadig & Voltaire suede clutchCanvas Jewelry layered necklace

Statement hosiery and your favorite little black dress

Of course, black opaque tights go with everything. But, what are particularly on-trend right now are patterned tights. Wear your new tights with your favorite black dress.

Statement tights and black dress | 40plusstyle.com

Karen Millen wool cashmere belted maxi coatKaren Millen zip front pencil dressIDIFU ankle bootNatori tightsThe Drop small toteSilvershake teardrop earring

Your winter date night outfits in one capsule

Below, you can see all the looks together in one capsule. You can see you can mix and match many of the items to create different looks. For example, you could wear the sweater with any of the bottoms, the red coat with any of the dresses or the red blouse with the red pants.

That way you turn every night into a date night if you wish!

Winter date night outfits | 40plusstyle.com

shop the winter date night outfits below:

Which of these winter date night outfits is your favorite? Let me know in the comments below!

Continue reading:

  1. How To Look Fashionable In Winter – Which Of These 11 Ways Do You Use?
  2. The Best Winter Coats For Women This Season And How To Choose A Coat
  3. How To Choose The Perfect Little Black Dress For Your Body Type

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Winter date night outfits to make sure you look good and stay warm | 40plusstyle.com

Feature image by Angela @angelamashelle


Sylvia is 40+style’s editor-in-chief and has been helping women find their unique style since 2011. She is devoted to empowering women of any age to look and feel their best. Read more about Sylvia and 40+style on this page.

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