5 Style Solutions For Awkward Date Scenarios

Well, with Valentine’s Day on the horizon, we’d be wrong not to address the two little buzzwords that have women’s websites all aflutter in these dreary February days: Date Night.

After all, looking Cute And Comfy™ is nothing less than a sartorial science. Especially when it’s 30 degrees out and you’re still rocking the Christmas food baby (and haven’t the heart to diet because hello, it’s freezing and there’s too much good stuff on Netflix at the moment).

Never fear, darlings. Whether you’re stoking the flames of a drawn-out Tinder flirtation or getting out of the house with your long-term manfriend, it really doesn’t have to be intimi-dating (NO SHAME). And whether it’s Dominoes for two or fine dining on the menu, we’ve got you covered. Here’s our quick and easy dress-up manual.

The Outdoorsy Date

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Okay, okay, so we all know the first Golden Rule of Date-Dressing: make sure you feel comfortable. But actually, this really applies. Don’t be the girl wearing heels on a romantic country walk, or a tiny body-con dress on a picnic (in February… well, it must be possible somewhere). Not that you would be, if you’re sane and living in the Northern hemisphere at this time of year, but still. Instead, listen to your heart: wear flats, layer up, and still look pretty. Because yes, you can indeed have it all.

The key piece: a super-cosy coat will keep you warm on winter walks. Normally your coat would be the first thing you’d remove, but if you’re outdoors, it’ll be the most important thing you’re wearing. Try faux fur touches; think of a traditional parka with a stylish twist, or a neat little biker jacket like this one from Zara. Pair with comfy boots and skinny jeans, silky hair and a big smile.

The Coffee Date

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If you were celebrating Galentine’s Day with your BFF, there’d be little reason to wear anything more than leggings and your old Ugg boots (because she loves you just the way you are). And so does your date, of course, but you want to show up looking a little prettified. Three initial golden rules: Make it a good hair day, first of all. Wear make-up, but go easy on them smoky eyes. And it’s probably best to keep your accessories minimal, because no-one in their right mind would need the Cosmo-approved statement necklace just to sip a latte at 11am.

The key piece: a plaid shirt is not the sole reserve of lumbersexuals; your all-time favorite wardrobe item remains the perfect versatile go-to piece. Make it stand out in your favor with skinny jeans, Chelsea boots, and your lucky earrings.

The Dinner Date

So your potential/actual beloved taking you to your local Mexican restaurant on a Saturday night: kudos to them, they know what you like. There’s no reason to get super dressy to chow down on nachos and beer, and you don’t want to look out of place, but you want to get, like, a little done up. Because it’s a date, after all.

The key piece: think Audrey Hepburn and her laid-back brand of chic with a great pair of cropped cigarette trousers. It’s not so much occasion to raid the fancy-dress box, after all, but you don’t exactly want to rock up in jeans, so find the best of both worlds. Add ballet flats, your favorite silky blouse (or cropped top, if your pants have a high waist), a bit of lipstick and some nice earrings … girl, you’re hitting the perfect balancing act.

The Expensive Dinner Date

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Well, you lucky lady, you. Mr./Ms Moneybags is obviously pretty into you! So, naturally, you want to look like the classiest version of yourself tonight, no? Forget the strappy heels and mini-dress thing: you’re not going to the club and, if I hadn’t stressed this enough already, it’s freakin’ February. And 2015.

The key piece: a ladylike midi skirt checks all the boxes. You’ll look feminine and pretty, nipped in at the waist, and on top of your style game (always a bonus). For girls who already like to be dressy, this trend is the bomb.com, but if you’re normally more laid-back, don’t be intimidated—find a relaxed style, pair with your comfiest heels or ballet flats, and let your hair down loosely.

 The Netflix-y Night In

The biggest struggle of all. Because there is a fine, almost imperceptible line between too much effort and … well, leggings and your Alma Mater T-shirt. Whether it’s a new-ish relationship, or you’ve both been off making sweet green all week and this is the first chance you’ve had to actually gaze into each other’s eyes for more than two seconds, then by all means there is a way to strike that perfect balance.

The key piece: beautiful lingerie. By no means do you need to go full-on Fifty Shades (unless you’re inclined that way, in which case, power to you). But a glorious new Victoria’s Secret set doesn’t need to stay secret for too long, and will make you feel primped and pretty despite your familiar surroundings. And if you’re dead set on actually, um, wearing clothes: Go for a silky shirt with leggings and bare feet, and freshly washed hair. Whether it’s a blossoming romance or you’ve been with Prince Charming for years, it’ll hit the spot. Wink wink.


What’s your perfect date night outfit? Let us know @litdarling! 

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