Your Winter Date Outfits Sorted

By Annabel van Eijk | Styles | 06/02/20
Your Winter Date Outfits Sorted

Baby, It’s Cold Outside, but that’s not stopping us from being swept off our feet and putting together fabulous winter date outfits. Whether you’re cosying up by an imaginary fire (aka Netflix) or heading outside for a first kiss in the snow, read on for a little inspiration for what to wear. 

The Cosy Cup of Coffee Date

So, you two lovebirds are just getting to know each other and decided to go for a coffee. He orders a flat white with oat milk, which is such a coincidence because that’s also what you always order and BAM you fall in love in the comfort of armchairs. 

Now, in that scenario what would you be wearing? Since this date is all about comfort I’d suggest you dress the part and wear something that is chill but not too chill. Something that says "I just threw this on as I would for any casual Sunday brunch, but I might head to something a little fancier after."

Start by wearing your favourite, comfiest and most flattering jeans, you know the one. Flared jeans are super flattering and give you that 70s babe feel matched with a cool statement tee. Pick a T-shirt that has something cool printed on it as a conversation starter or one that just shows you have great taste in bands. Then throw over a knit or sweatshirt, whatever suits your style more or whichever you love the most. Then I’d go for some ankle boots that are comfy yet chic. This look works for a cosy cuppa coffee, but take off the jumper and you might just be ready for dinner and a drink after…

Winter Date Outfit

The Full-On Winter Wonderland Date

Yeah sure, picnics at the park are great but have you ever had a Winter Wonderland Date? Ice Skating, walking around town and ending in a snow fight or doing anything a little Christmas-y like visiting a Christmas market. You know, all your usual cheesy rom-com stuff. You're the star in this rom-com (move over Kate Hudson) and you look so “Winter” you might as well be a living Pinterest board. 

Go all out with typical winter accessories. A cute matching scarf and beanie will do the trick,  if you don’t mind splurging a little on a little luxury, then I’d suggest having a scroll through our selection of cashmere goods. Use your date nerves as an excuse to luxuriate in all that softness, I won’t judge you.

Yes, you’ll be outside so that means your main priority is to stay warm, but that doesn’t mean you have to show up in a ski suit and Moon Boots. You simply can’t go wrong with a sophisticated wrap coat, preferably in a chic camel shade. For more warmth and a wintery feel, wear a knitted turtleneck under. I’d go for a pair of wide-legged pants and some comfy white trainers (with extra warm socks) or you can wear a skirt or dress under your jumper with a pair of warm Heist tights. For shoes I'm thinking high boots that have a bit of a heel but are still good to walk in unless there’s snow out, then it’s probably a better idea just to go for a pair of flat boots. 

Winter Date Outfit

The Fancy Night Out Date

Oh oooookay you’re going to a fancy restaurant or bar for a sexy, splurge-worthy night out? Whether you’ve just started dating or it's been forever, once in a while a fancy date is just a really great excuse to look, damn, good. So don’t be afraid to go all out when it comes to this winter date outfit.

I'm personally an advocate for having at least one classic black jumpsuit in your closet, it’s a serious one-hit-wonder for lots of different occasions. For this special date, you can dress it up a little with heels that you’ll feel like a goddess in.  Jimmy Choo Heels are not exactly the most original of ideas in this blog, but they really do work. Throw in a clutch that you never wear because it’s totally unpractical, but you’re on a date night so you can make an exception. For a night like this, I like to throw in some unexpected details like big earrings, this will show a bit of your personality and less like a “date night uniform”. To continue on this note you want to look a little vavavoom, but that doesn't mean you have to conform to a Little Black Dress uniform - that's why I love a jumpsuit. 

To finish the look, throw over a really cool printed or coloured coat for that little stroll around the block after drinks, or hopefully that long romantic kiss in front of your doorstep.

Winter Date Outfit

At Home Snuggles Date

You've been through the works of drinks at a nice bar, a coffee date, etc. and now It’s snuggle time! Maybe he invites you over to cook for you (THE DREAM) or maybe you invite him over to watch a movie and hang out. I’m personally so here for the cosy snuggle part of dating, but after a few months with my boyfriend I have a stash of clothes in his closet that can be labelled “Comfy Clothes”. Because who the hell wants to sit and watch Netflix in the stuff you wore during the day? But when you’ve just started dating, it’s not very likely you’ve got that pile already at his place or if it’s at your place you might feel like a little bit of a mood killer to say “Brb now is the time I change into something comfortable.” So, in that case, you will have to think a little tactical on this winter date outfit.

Of course, you want to be super comfortable so that means no rigid jeans or tight pants that won’t let you laze into the comfort of a couch. I’d suggest going for a pair of comfy Heist tights (as a bonus they also have a shaping effect at the waist) and a flirty-but-not-in-an-obvious-way dress, this will feel just like you’re hanging out in your leggings! You can add some subtle jewellery and throw on a comfy sweatshirt and voila! Snuggle away, my friends. 

date night outfit

Hopefully, this will help take the nerves out of figuring out your winter date night outfit out a little. You'll have much more time worrying about other stuff! No, in all serious dating should be fun and you should dress in whatever makes you feel yourself and comfortable. Not a heels girl? Don't wear heels. Can't get yourself to wear something "chill" for a casual date. Wear whatever makes you feel confident! 

Love AnnabelAnnabel van Eijk
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