Winter date night outfits: All the style solutions you need to know for 2023

Image courtesy of H&M

Kicking off Jan as you mean to go on with date nights in the diary, but no clue what to wear for going out in the depths of winter? We’ve found all the outfits to sort you out, from the best dresses to the new trousers and tops combos to know.

Lottie Franklin

5 January 2023

My New Year’s resolution is to go on more dates, but every time I look at my wardrobe, I’m bored with all the clothes I have and can’t decide what to wear. I don’t want to spend much money (I’m still recovering from December!) but could stretch to a couple of new things to give my winter date night outfits a lift. What are my options?
Claire, Chelmsford

We’re in the depths of cuffing season, so it’s no wonder the first week of January is the peak time of dating app downloads, stirred up by that New Year fever. With festivities out the way, January’s also a time notorious for looking after yourself, so for anyone partnered-up, winter date nights are a sure-fire way to beat those January blues.

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You’re also not alone if lots of new purchases aren’t on the agenda right now and, like us, you’re watching those purse strings after indulgent Decembers. But as Bianca talks about in her recent column, January is a good time for re-evaluating wardrobes and slowly adding in a few key pieces for the year ahead – pieces that are perfect for winter date night outfits when you want to feel at your best and completely yourself.

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According to Hinge, 75% of their global singles say going to get drinks is no longer their preferred first date activity, whereas meeting for coffee, doing something creative, seeing a show or exhibit, or simply going for a walk would be their ideal date instead. But what on earth do you wear for a first date outfit when it’s freezing and raining outside?

Whether you’re single or coupled up, we’ve got plenty of new ideas for winter date night outfits that you’ll feel comfy and confident wearing, whatever the New Year throws at you…

Scroll for winter date night outfits, from going-out winter dresses to luxe loungewear

If you are going out and dressing up for a winter date night, like it or not, you’ll be needing layers – you don’t have summer’s sun-kissed luxury of warm evenings and wearing no sleeves or jackets. But for date nights, layers feel, quite literally, stuffy. Where’s the fun and sexiness of a big jumper on a night out?

Dressy winter date night outfits

Let’s start simply with the classic little black dress. Yes, you want to wear clothes that keep you warm when it’s freezing outside, but you can still feel dressy – just look at this Reformation sculpting knitted dress, River Island’s knitted mini with long sleeves and Karen Millen’s slouchier midi that shows some cleavage, with a subtle slit up the leg.

Then layer one of these coats on top of your dress for the journey to your date spot.

As another option, you can add a luxe blazer or fur coat to a satin slip dress like this one from Reserved. Just read our guide on how to style winter slip dress outfits for the new season. I love this Sofia blazer from All Saints, which is massively discounted in their sale at the moment and comes in both velvet and satin.

Trousers and tops combos

More of a trousers gal? Invest in a satin pair for the new season. The Karen Millen trousers come in a matching suit set. Alternatively, look to my edit of the best leather trousers and how to wear them for winter.

You can also tuck a thin roll neck jumper into one of these statement skirts for a chic winter look. Just add tights or knee high boots.

Try a new satin top with your favourite jeans for a quick outfit revamp.

Or for a date night look they won’t forget, invest in a black lace top. If you need a coordinating bra just look at my edit of what to wear under sheer tops.

Bring out a diamante top for ultimate main character energy.

Add some glitz with a special going out bag.

Low-key date night looks

For date nights where you’re going somewhere local and low-key, reach for a new statement knit, shirt or winter dress.

I love this cute and cosy matching set from Mango which couldn’t be seen as either too smart or too casual.

These knitted tops are also a subtle and stress-free option for date nights – they’re smart enough to look like you’ve made an effort but not OTT.

Cosy nights-in clothes

These are the dresses that say, “oh, you’ve been working from home in this all day but still look sexy”. Knitted dresses aren’t going anywhere for 2023 and these are my favourites on the high street right now. I’ve picked out darker shades in case you’re staying in and cooking a meal for a cosy winter date night at home.

Planning a cosy night in (or for your winter date night to carry on all weekend), get yourself some luxe loungewear. You’ll never regret investing in some silky separates or snuggly co-ords, whether someone sees them or if they’re only for yourself.