Winter date night outfits to make you irresistible on your next date

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

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

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 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.

Karen Millen military jacket – Chelsea28 cuffed midi dress – DREAM PAIRS thigh high boots – Zadig & Voltaire suede clutch – Karine 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.

Nordstrom wool & cashmere double face coat – Karen Kane faux wrap dress – DREAM PAIRS thigh high boots – ALDO clutch – Silvershake teardrop earrings – Acotavie silk scarf

blazer with jeans and long boots

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.

Eliza J velvet blazer – Halogen cross front satin top – Reformation skinny jeans – DREAM PAIRS thigh high boots – Zadig & Voltaire suede clutch – Nordstrom 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.

Ted Baker London wool coat – M.M.LaFleur off the shoulder sweater – Ted Baker London handkerchief hem skirt – DREAM PAIRS thigh high boots – ALDO clutch – Nordstrom oval earrings – Maybelline 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.

Ted Baker London longline jacquard knit cardigan – Boden silk shirt – Karen Millen leather dipped trousers – DREAM PAIRS pump – Zadig & Voltaire suede clutch – Canvas 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.

Karen Millen wool cashmere belted maxi coat – Ted Baker London printed shirt dress – IDIFU ankle boot – No Nonsense opaque control-top tights – Zadig & Voltaire suede clutch – Karine Sultan pendant ear jackets

Turtleneck dress to keep your neck warm

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.

Karen Millen notch neck coat – Nordstrom pleat shift dress – Nine West pump – The Drop small tote – Silvershake 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.

Caracilia faux fur stole – Black Halo jumpsuit – DREAM PAIRS pump – Zadig & Voltaire suede clutch – Canvas 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.

Karen Millen wool cashmere belted maxi coat – Karen Millen zip front pencil dress – IDIFU ankle boot – Natori tights – The Drop small tote – Silvershake 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!

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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Feature image by Angela @angelamashelle

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