I met a couple of my closest girlfriends on an evening last week - a dinner at Chiltern and then off to our favourite Marylebone spot for a cosmopolitan (or 5) - and we got to discussing our dating lives; shock, horror. Is it really a night out with your single friends if you don't mention your love life at least once? After an unsurprisingly brief round up of recent developments, we simultaneously reached the natural conclusion that it was time to dive back in to the deep end of the dating pool, after dipping our toes in a rather blasé manner for the better part of a year - another caveat of being single with your friends is have so much 'single fun' that you keep each other from seriously dating, even subconsciously.
At a late coffee catchup the next morning we got to it, setting each other up with friends of friends, finding the seemingly perfect match and planning dates with potential suitors to take place this week - on a Tuesday. We figured that we could make all the plans on the same day and all reconnect on Wednesday evening over a drink. Of course, being different people, we all like to date differently: I opted for an early dinner with the pilates instructor I have been flirting with for 4 months, while my best friend set up a coffee and walk around Richmond Park with a friend of mine who works out there, and one of us agreed to see Tom Holland in Romeo + Juliet, followed by drinks with a finance guy who's been pining after her for far too long. The point I'm trying to make is: first dates - and subsequent dating - come in all shapes and sizes (how liberal).
Tuesday came, the group chat starting pinging at 10:00am - naturally, the pre-date jitters had begun, we were all flexing unused muscles of course - but the first text was as follows 'HELP, what on earth am I supposed to wear?!!'. I gave my typical day to day style tips and wished her luck, thinking nothing of it. It wasn't until the evening rolled around and I had received almost the same exact message from 5 of 7 girls in our little circle. I had a moment of realisation, styling outfits when dating is it's own competitive sport! So many unspoken rules, so many new circumstances, so many questions... What will my date be wearing?? Do I plan for comfort?? Should I be dressing to impress?? How do I make sure I look like myself?? Essentially, you build up the confidence begin dating, and then are hit with the first of many hurdles.
So, I decided to put together a comprehensive list - perhaps more of a crash course - of what to wear, the unspoken rules, dos and dont's, my tips and tricks, for every type of date, from coffee, to the opera and everything in between (with curated contributions from the most stylish among my previously mentioned circle, thanks for the inspiration).
Before we get specific, I thought it was only right to begin with some general tips. Things that apply to any location or time, regardless of whether it's date no.1 or 10:
Dress for yourself first: when you're dating, it's easy to lose track of ourselves in the endeavour to present the person we want to be, or that we think our date wants us to be. Enough of that. Make sure that the way you dress is a truly honest and unapologetic representation of yourself.
Live in a signature scent: my top style tip for everyone, dating or not, is to find your signature scent and really stick to it. Personally, I have been wearing the same single scent since I was 15 and I receive as many compliments on it today as I did all those years ago. What's more, everyone I have ever dated has told me they associate that specific scent with me and whenever they smell it, they can't get me out of their mind; this might be a slightly dark tactic, so proceed with caution, but if used correctly you can add another incredible layer to not only your outfits but your entire presence.
Keep track of your closet: now this one may be a little trivial, but I care about these sorts of things (at least I do when I start dating someone new). Keep in mind which outfits - or even just statement pieces - you have worn on previous dates and which outfits you plan on wearing in the near future with the same date, as you (or at least I) don't want to get caught wearing the exact same thing, even by chance.
Ensure your outfit is appropriate: perhaps this is the most important of all. You must take into account many factors when getting dressed for a date, as anything such as your comfort, the weather or just the type of date/event can play a huge role in what you wear, and consequently whether you have a great time on this date or not. More specifics to come later but think... something longer for evenings, appropriate footwear if you are walking, not too much - or at least waterproof - makeup if it's sunny.
And as promised, here is what I would wear and take into account when dressing for each kind of date...
First Date
This one is tricky, it's either you first time ever meeting someone new, or if it's someone you know, you are seeing them - and they you - in a completely new context. You want to dress up and look your best but not be overdressed. Make sure you look and feel your most confident self, but more importantly, dress to communicate your most authentic self as it will help you present the true you and stick to your own morals, opinions and values for the whole date and potentially relationship. The first date always feels so monumental, but I like to remind myself that it's never that serious. Make it fun, throw on a statement piece that brings you a lot of joy, this will also double as a topic of conversation later that will allow you to talk about something you care about - passion is sexy - and create a connection with your date, all from a piece of clothing! So, regardless of the type of date, stick to your true style and opt for statement piece that represents you.
Coffee Date
This is at the top of the list for the most casual types of date, so let yourself present as such. It's the time to lean into your street style, play around with layering, do something more comfortable and casual. It's a great chance to go for some funky sneakers and opt for a cosy knit. Although you want to dress it down a little and aim for comfort, I find it helpful to consider a few things, just for some direction (as you still want to feel and look stylish): 1. focus on a minimal colour palette - perhaps sandy neutrals or earthy tones - 2. think about balancing different patterns - block colour on the bottom and stripes on top - 3. find an interesting piece you want to wear and build your date outfit around it - find materials that clash but in similar colours, or even pull ideas for each item of the outfit from all the different colours in one statement sweater?
My point is, dressing more casually doesn't automatically mean you can't be intentional.
Movie Date
Time for Ultimate Comfort Mode. Comfort is super important in the movie theatre so remember to lean into it, because regardless of how hot your date, how incredible the movie or how perfect those movie snacks are, you will leave feeling like you had the worst time if you are uncomfortable. But wait! I have to remind you to never do JUST a movie date, this should always be accompanied by dinner, or drinks or at LEAST a coffee, so when planning your outfit for the date, keep in mind the context of the entire date. We love to be comfortable in the theatre, but if you are going to dinner after... you better ensure that you are looking 10/10 after sitting in a plush seat for 2 hours. In terms of actual styling ideas, maybe play into the style of the lead actor/actress of the film you are going to see, maybe just in theme with the movie itself.
Rather than a fitted jean, opt for a flowy pant like a wide leg or palazzo (but be aware of creasing and stains (perhaps just keep that popcorn grease away entirely). I am a huge advocate of a jumper tied over your shoulders, not only does it add some level of detail and intrigue to an outfit by layering, but it's so incredibly functional for evenings like these, where it's nice to have a comfy layer to snuggle up in (and use as a stain protector) but still be able to have a lovely evening dinner outfit underneath.
Lunch Restaurant Date
First things first, you have to take into account the type of restaurant you are going to, ensure that whether it's a quick and easy street food joint, a mid range meal or a classy high end establishment, you are dressing for the occasion. Generally speaking, lunch is just a more casual version of dinner (dress code and even etiquette wise). Rather than a jacket for men, you'll get away with a good shirt, for women, you can play around with a dress that is slightly shorter or just ditch the dress and wear a set, or a nice pant/top combo. Evening pants can become jeans, jewellery can be bigger, more funky, more loud. Wear your hair completely naturally. Essentially, lunch dates are your chance to makes some bolder, louder choices. Opt for a more 'risque' neckline, you are able to get away with a little more shoulder.
Evening Restaurant/Dinner Party Date
This is the more formal version of lunch, with a side of sexy. Wear a more deep, dark, sensual scent, add a bold lip or smoky eye, simplify the outfit to 1-3 pieces, choose a higher heel, pull back the hair and add some product. Keep it classy, don't get your entire body out but by all means let a single shoulder slip slightly out, maybe let your hair fall over one shoulder to reveal your neck. Opt for a bold lip that you wouldn't typically reach for. Men (if you are actually reading this), it is still the best choice to throw on a jacket, but please don't call it a night there. There are more choices out there than just the stiff, ill-fitted blue/white shirt you wear more than twice a week to your desk job. It's summer, you can pull off a perfect white tee with a sweater vest for that artsy vibe, you can choose a relaxed linen shirt and unbutton it one more than you ought to. Ditch that jean and find something a bit more formal, even a flowy linen pant or a perfect fit chino.
Whatever you do, DO NOT show up to a first date in CARGO PANTS!!!!!!!! That's all.
Walk/Casual Date
It's always the best way to get to know someone, have no plan, no agenda, just start walking and see where the world wants to take you. It's a little casual, a little playful, and you NEED to think about your shoes. The worst thing (similar to the movie date) that can happen on a casual, walk date is that you are in the middle of the best conversation, having fun and getting to know someone incredibly well, but then having to cut it short because your feet hurt or your outfit is just falling to bits, or you are way too cold, or hot. Make sure you think ahead and layer/style in a way that your clothes won't get it the way of you moving, but so that they can also transition from hot to cold or vice versa depending on the length of this date or weather or time of day. Always go for a reliable sneaker and a pant that won't drag on the floor or get caught up in the dirt/gravel you inevitably kick up. Don't layer up in the thickest knit you own because you'll catch yourself dripping 5 minutes in, and not for the right reasons ;) We're aiming for glow, not grease.
Sport/Workout Date
Now this is a fun one. Make sure - if you are playing a sport - that you are on theme for such, without acting like it is a dress up, costume thing. If playing tennis, stick on some Ralph Lauren, a trusty pair of fitted shorts and some ON sneakers, don't go nuts with head bands, wrists bands, dramatic poofy 'tennis' skirts. Function over fashion is always going to be more stylish and authentic, believe me you'll look a lot more stupid trying to hold your tacky cap on your head than you would just wearing a simple, functional outfit and getting into the game. As for working out, black is the way to go, you can't deny that at a workout class - especially with a date - your body is exposed and don't lie, you are looking at your date too - and everyone looks good in black, find something that is form fitting, shapes you in all the right places and fits like a glove, but most importantly, something that you feel safe and comfortable in so that you can actually enjoy the workout, you want to feel and look good, not spend an entire 45 minute spin class sucking in for the approval your hot date.
Theatre Date
Now this is where it gets good. This is another chance for a little method dressing, wear something that's more appropriate for the story of the performance you are going to see, something from the era it is set in, something a little more literal that a character might wear (as long as it suits you and is something you genuinely would wear) once again refraining from becoming a caricature. Think the Dinner Date allure, mixed with the movie date comfort, because I will die on the hill that NO THEATRE SEAT ANYWHERE is comfortable to sit in for almost 3 hours. My theatre rule for myself is no jeans, both for comfort and just as a bare minimum level of 'dress-up'. If you are going to a musical, it's a little more fun - choose a bright coloured statement piece or something funky accessories. If you're heading to a deep, thought-provoking new work or Shakespeare, perhaps lean into a little more refined, subtle, artsy vibe with a duller/darker/neutral colour palette or less dramatic accessorising.
Opera/Ballet Date
My favourite of all, a black tie affair. If it's opening or closing night, or even a gala performance, men in full black suits. Anything else is as follows, opening night or not, women should be wearing something absolutely modest, and either ankle length or floor length. Think practicality, you need to dress up but this is not about you, so don't wear a huge poofy tutu skirt because you think it's cute for the ballet, don't stick a fucking tiara on your head and definitely don't wear a dress with a train!!! Opt for darker, neutral colours and simple (ideally block colour) designs. This is not the time or place for a high slit, it's not the time for trainers nor is it time for chunky platform shoes. Opt for a nice classic high heel or kitten slingback. Show your date how stunning and sexy you can look without revealing everything to the world. Men please just have faith in a classic, elegant suit, you can choose anything from a cool grey-blue, to a deep - DARK - jewel tone. Try a velvet texture, or a linen (please steam it) and make sure your footwear is in-keeping with the opulence of the evening, perhaps an Italian leather Chelsea boot or Loafer.
Bar/Drinks Date
Now this one is hard... Personally I love a drinks date (not in a crowded corner pub at 6pm on a Friday, more like a nightcap in a hidden jazz club on a Wednesday) but I really don't think it's ever the right option for a first date, regardless of whether this is a friend you already know but want to date romantically or if it's a complete stranger, casual drinks are never the appropriate context for the first date. However, from date 2 onwards I think you just can't go wrong. Girls, this is the time for something sexy, sneaky and fun: try a maximalist oversized fur jacket over a mini-mini dress, try a sky high stiletto paired with a short short, try a print or pattern that would get a gasp in a nice restaurant.
Those are my beginner friendly, simple styling tips for dating. I hope that something has stuck with you or given you a little inspiration to try out something new, or even go on a date... So now, ladies (and gentlemen, if there are any left) please go out, look fabulous and never split the bill.
Catch you next time
XOXO
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