The ultimate guide to dressing for a first date: Style do's and dont's

Dating can be really intimidating, especially when it comes to first dates. Will they like you? What if they leave early? How do you avoid awkward silences? What if you spill red wine all over him, or worse, yourself? There are a lot of things to worry about — which is why it’s important that our date outfit isn’t one of them.

If you’re still feeling anxious about that date you’re looking forward to, or if you’re in need to up your A-game, then look no further. Here, we’ve gathered some tips and tricks to ensure that whatever happens on your first date – an outfit disaster won’t be on the list!

Do...aim to make a first impression that lasts

Yes, we agree it’s not fair but yes, it is a fact that first impressions last a lifetime. What we wear is part and parcel of how we choose to present ourselves. Personality will always outshine aesthetics but no one knows your personality until they get to know you…whereas your outfit, hair and makeup is the first thing people see about who you are.

So, with all that in mind, when you’re on a first date he’ll have made some assumptions within the first 5 seconds of laying eyes on you.

To really nail it, you want to show him exactly who YOU are as a person, but also just the best version of you. Don’t try to source a new style that isn’t how you normally dress…just give your personal sense of style that extra kick for the date.

The aim is simple: make him go WOW in his head as soon as you walk through the door.

Milah Asymmetrical Bodysuit, $33.90, Love Bonito. Buy it here

Do...give off that ‘effortlessly cool’ vibe

Eh? How do you be effortlessly cool? Good question, we’re glad you asked. What we mean by this, is that you want to show him you’re naturally stylish and chic, but look as if you’ve just thought about it all last minute.  As if you throw on anything and look instantly appealing.

Certain items deliver such chilled but stylish attitude, such as loafers, oversized cardigans, double denim shirt and skirt combo, sandals and socks, ripped jeans layered over fishnet tights, crop top and ripped shorts or even just simple black skinny jeans and heeled boots. Throw on a hat and large sunglasses and you’re THAT girl everyone wants to be or be next to.

Asymmetric Wool Jumper, $119, H&M x Toga Archives. Buy it here

Do...make comfort a priority

Listen, it can be the most stunning and most beautiful dress in your whole wardrobe, but if it’s uncomfortable then you’re going to have a crap time. You’ll be too busy focusing on how you wish you wore that softer maxi dress and you’ll not be able to pay proper attention.

Your discomfort will be projected onto him too, even if you don’t realise it. It’s also more likely to make you ditch the date early rather than just going with the flow and seeing where it leads.

Yes, looking great can often be slightly uncomfortable, but you need to find a balance on a first date and if you have to choose, make comfort your priority.  You need to be physically relaxed to show him how awesome you really are.

Puffed Sleeve Mini Dress, $44.90, Pomelo. Buy it here

ALSO READ: 4 cute outfits for a weekend brunch date

Do...prepare for the unexpected

You need to be ready to go with the flow…if you have the best time and he does too, you both will want to hang out beyond the ‘planned’ date activity. So, always be prepared for the next adventure.

This means taking another layer should you get cold in the evenings, and packing a pair of flats that are handbag sized, so you can make a swift change if he wants to go off exploring post-dinner.

We’re not saying bring a bikini in case he decides to go swimming — you have your own boundaries. Besides, it’s the first date after all… the ‘first’ being the keyword here.  But do think about possibilities beyond just the one cocktail at the bar.

Grosgrain Snake Print Slide Sandals, $46.90, Charles & Keith. Buy it here

Do...rock jeans or leggings if you’re on a casual coffee date

Coffee dates are common and the nicer option for those who get panicky about a first date, because they take a lot of the pressure off.  A daytime coffee date doesn’t seem as scary as a dinner date where you’re forced to eat a 3-course meal opposite this stranger and you’re sure you’ve got herbs in your teeth but can’t go check as you just went to the loo five minutes ago.

For the coffee date, we say jeans or leggings are the basics of your outfit. This is because when you’re sitting down for a while, you won’t get the chair marks in the back of your legs upon standing up.  

It’s also because they give more of the ‘casual’ feel over skirts or dresses – shorts are also okay too. You want to dress similar to how you would go for coffee with your best girl — just with an extra spruce up!

WOMEN Skinny High Rise Ankle Jeans, $69.90, Uniqlo. Buy it here

Do...hug your curves

Femininity plays a huge role in first dates. Men are attracted to our femininity as the antithesis of their masculinity — it’s all down to basic genetics. We don’t want to put ourselves completely on show, but we do want to flaunt our curves.  So, think about your outfits in a way that will emphasise and flatter your silhouette.

Think — waist belts, pencil skirts and tops, sweetheart necklines, tailored dresses and jeans. Anything that makes your body type shine and works for you.

Checkered Halter Keyhole Dress, $44, Pomelo. Buy it here

Do...scope out the date venue beforehand

This is an absolute must in order to nail your outfit.  No one, we repeat no one, wants to waddle through Botanic Gardens in thigh high heels boots. Nor do we want to sit at The Mandarin Hotel bar in our last season floaty maxi dress and flip flops.

Work out what the venue is before you go on the date to ensure you can dress appropriately and actually enjoy yourself.

If you’re stuck or have no clue on what or where you’re going, play it safe with some leggings, ankle boots and then a long tee or dress layered over the top, complete with a blazer. This means you’ll fit into most scenarios and if the beach beckons, you can roll up the leggings and get splashing.

Faux stretch-leather leggings, $147, Commando. Buy it here

ALSO READ: 8 best Taobao clothing stores for all your fashion needs

Do...nod towards one key trend

While some men would often say that they try to avoid high maintenance girls, they also do like women who take care of themselves and follow fashion.

We advise that, whilst you should express yourself however you see fit, including a nod to a fashion trend will give off the ‘I am so together’ vibe.  It can even be just the colours chosen or a small accessory for extra fashion points — take, for instance, the mini bags that are bang on trend this season.

Mini Saddle Bag, $4,600, Dior. Available at the Christian Dior boutique at ION Orchard

Don’t...wear inappropriate date activity attire

This is why we say, you have to check out the date venue beforehand! There’s nothing worse than rocking up in your best LBD and new Louboutins only to realise he’s standing there in shorts, flip flops and a picnic basket.

Dressing to match the occasion is a surefire way you’ll feel most comfortable and at your best. If it’s beach-themed, go with flip flops and shorts. Dinner date? Dress and heels. Cinema? Jeans, boots and a cami tee with a cardi for when it gets chilly.

If he insists on a ‘surprise’ date then you can at least just ask him for outfit guidance. If he still refuses…then he can wear your heels through the sandy beach at 9 pm at night.

Marlo Asymmetrical Column Dres, $59.90, Love, Bonito. Buy it here

Don’t...wear an outfit that requires constant adjustment

There is nothing more off-putting than watching someone constantly shifting in their ensemble, pulling down sleeves or pulling up straps or pulling down skirts. Sure, the occasional adjustment is possibly needed but when it is non-stop, it is very annoying.

Plus, it can give you that air of ‘nervousness’, even if you’re not. On first dates, we want to be approachable, chilled and confident, not shifty and nervous.

Do: Try opting for comfortable silhouettes that are easy to pair with, and are super versatile just like this dress.

Catching Daylight Midi Tiered Dress, $139, Klarra. Buy it here

ALSO READ: White tees so chic you'll want to wear them on repeat

Don’t...slap on the makeup

Whilst this isn’t technically fashion related, it’s too much of a poignant tip for us not to include. Men will always prefer naturally attractive women — just as we prefer naturally attractive men. Call it human nature. When you pile on so much makeup – even if it is just a lot of base makeup, believe it or not, they can tell. They’re not silly!

Wearing too much makeup sends off the signal that you’re unhappy with how you look naturally, or you’re in need of all that slap, and it also gives a ‘she’ll take forever every day to get ready’ vibe.

Do: Instead, try opting for a natural look. Take, for instance, replacing your heavy coverage foundation for a lighter base and a soft palette for your eyes.

Don’t...dress as if you’re on business

Whilst after-work dates are common and so much fun, if you have to dress extremely cooperate for your role, we’d say do not head straight to the date in the same ensemble.  This is because office or uniform wear can often give off that ‘unapproachable’ quality that we’re trying to avoid at all costs.

Do: Being a career girl is epic but you need to show that you can unwind and have fun beyond the office too.  If it’s completely unavoidable, simply ditch the blazer and swap the starched shirt of a softer top, and pair of trousers or a flowy skirt, like this number, with a pair of sexy heels.

Slip Skirt in Sand, $69, Klarra. Buy it here

Don’t...wear something too tight

This comes hand in hand with the ‘don’t put it all on show’ tip, as too tight can make you seem like you’re up for it again.  However, it also means you’ll often get caught up with unsightly lumps and bumps because of your ill-fitting garments.

Whilst figure-hugging items are great for displaying your best assets, if you go too far the other way, they can actually make you look larger than you are. Oh and lest we not forget how impractical it is especially if you’re on a dinner date — you need room for that chocolate dessert!

Do: Alternatively, you can opt for flattering silhouettes that are not too figure hugging, just like this cute piece from Zara.

Short floral print dress, $69.90, Zara. Buy it here

Don’t...stroll up in jogging bottoms, trainers and a cap

Okay, so this isn’t quite the hard and fast rule because if you’re both heading on a skateboard or rollerblading the first date, then casual sports attire is fine.  But generally, don’t turn up looking like you’ve just rolled off your sofa and made no effort at all.

If you look like you’ve made zero effort and put no energy into your attire, it shows him that you don’t really care enough about the date, or him. It also shows him that this is the ‘best version of you, meaning it won’t get much better than that.

Unless he’s extra sporty, he’ll probably be put off with the ‘I couldn’t be bothered to try’ too-casual ensemble. It works the other way round too.

Don’t...be overly ambitious with your outfit

Yes, making a good first impression is key, but don’t go over-the-top with your outfit as you’ll probably end up getting it all so wrong.  The ‘less is more’ statement applies, in that you need to look like you made less effort but still got the top-notch end result.

Men seem to swerve away (far far away) from girls that come across as high maintenance and hard work. If you dress with too much effort, whilst you have good intentions it does tend to be a bit ‘try hard’ or as if you’re going to constantly dress this way.

Let him see the real you, but just the best version.

ALSO READ: 12 cute cardigans you’ll want to wear to the office & after

Don’t...scrape your hair back tight

The sweltering heat can make hairstyling a huge chore. Your hair won’t stay up in a bun, it won’t stay straight, and it won’t stay curly — it’s just an ongoing nightmare.  So, we understand if your default hairstyle is to scrape all your hair back into a tight ponytail and have done with it. Sorted.

Yes, sorted for a Friday at the office, but not so for a first date.  You see, there is something about scraping your hair back tight that gives off the ‘unapproachable’ vibe. At times, it comes off as a little too serious.

Do: Instead, roll with loose playful hairstyles that make you look cute and more ‘girl next door’.

Don’t...reveal everything all at once

We can’t express this enough — no man wants everything on a plate in front of him and if he does, he ain’t no man you want around! The aim of a first date is to ensure he wants, nay needs to see you again. If you wear next to nothing, he’s seen it all from the get-go and will thus not need to repeat.

When you wear something super revealing, it portrays a certain ‘girl’ that you do not want to be. In laymen terms, up for it. You look like you’re there for a good time, not a long time.

Don’t...apply too much or too dark lipstick

Dark lipstick, along with tight ponytails and business suits, will be a ‘stay away’ warning sign to a man. Whilst dark lipsticks are so fierce and a staple for our weekend plans, we say leave them at home on first dates.

Aside from the ‘ferocious’ feel to a dark red or purple, they’re also a huge huge kiss-ruiner. As is any shade where you’ve layered it on and on — even nude lipstick can be a kiss-ruiner if you’ve got five layers to contend with.

First dates and first kisses are magical, so don’t let the darkness ruin it!

This article was first published in Her World Online.