Style Tips

What to Wear on a First Date

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Customer Happiness Team

February 3, 2018

When it comes to first dates, the question that everyone seems to ask is ‘does it really matter what we wear?’ The answer to that question is simple. Yes, it really and truly does. Although that may sound incredibly vein, chances are if you had a job interview for your dream job you probably wouldn’t even think twice about it. The reason being is that you would want to put the best version of yourself on display in order to give yourself the best opportunity at scoring that dream job!


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Although it may seem a bit far-fetched and whether we like to admit it or not, first dates are usually a lot like a job interview or can end up seeming that way. You’re undoubtedly nervous answering a 100 or so questions and desperately trying to sell yourself in a bid to potentially meet Mr. Right, even if that means having to meet a few Mr. Wrongs along the way.

The thought of a date failing may seem daunting, but it’s actually not. It should, in my opinion, be seen as an adventure and as a beckon of opportunity for the young and fashionably enthusiastic single girl. Dating means the pleasant curating of many fabulous outfits, which of course can only make a girl feel better.

So now that we have identified that you should dress your best on a first date (no brainer there), we really need to take a deeper look at what you should be wearing and how to dress on a first date.

Good news is we’re about to make it super quick and easy with our simple 7 step checklist guaranteed to help you capture the perfect first date look.

Easily navigate through our list of fail proof Do’s and Don’ts below and you’ll be head over heels in love in a matter of minutes.


Seven step switch: A mindset switch on the rules of date night fashion.

1. Do plan out what you are going to wear

The reality is sometimes people just need a plan! Some people just operate better when they are organised and ready to go. So as over the top as this may seem, it’s probably going to help some ladies out there ease their pre-nerve date jitters. My only piece of advice to those of you who want to plan ahead is three words ‘keep it simple’. Once you have picked out an outfit, just move on! Don’t dwell over your decision, just roll with it and let your personality do the rest! See above OUTFIT PLAN EXAMPLE (Always have a backup option just in case but only choose one).

2. Don’t try new trends, stick to your personal style

While most of us females are suckers for a hot new fashion trend, most of us are also well aware of the fact that it’s not always going to work out the way we envisioned it in our heads. The sad truth is that more than likely we have not been inheritably gifted with the qualities of a 6 foot supermodel. We therefore risk the consequence of becoming what is commonly coined in the fashion industry as ‘fashion roadkill’. Not to discourage the enthusiastic fashionista out there who swears by the pages of vogue, but you may want to tone it down a bit. Guys are generally not that fussed over high fashion. As far as they are concerned some fashion looks like their grandmothers doily teapot cover. So as a rule of thumb always keep it real and keep it you!

Read Also Bad Romance – The Perfect “Anti-Valentine’s” Valentine’s Day Look

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3. Do wear a colour that suits your skin tone

By the time most of us start entering the dating game, we have long ago discovered that there is a colour palette outside the realms of baby pink and blue. It’s safe to say that as a young adult we have had countless experience in playing dress ups and should be well aware of the colours that suit and don’t suit our skin tone. Our skin colour is a part of our genetics and makes us who we are. It can also however determine what colour tones best work with our skin. That’s not to say that we can’t all for instance wear the colour yellow if we want to, it just might not work to the best of its potential on all of us. Always try picking a colour that you know suits your skin tone to guarantee feeling as radiant as ever. Know what works for you!

4. Don’t wear anything you can’t walk, breathe or eat in

This my friends, is probably the most important point mentioned here today. Don’t ever, and I mean ever, think its ok to wear a dress two sizes too small or stilettos so steep that your Achilles’ heel might just snap. Your intention might be to look super sultry and womanly for your date, but the reality is you can never put a price on a women when she is feeling comfortable and confident. So please ladies, don’t opt for smaller clothing options to make you feel thin, because you won’t and chances are you will only end up feeling more exposed and vulnerable. A great tip I personally like to live by is when in doubt get the bigger size and alter it to fit your body. Nowadays most outfits are mass produced and sizing has become skewed. This clearly does not work as all females have different body types and shapes. Pick comfort over sizing and feel like an all-round winner.

5. Do stick to what works best for your body type

We all know what silhouettes and shapes work best for our body type. If you have an hourglass figure you probably opt for form or figure hugging dresses to complement and accentuate your curves and waist. Whereas if you are of an athletic build you perhaps will steer clear of outfits that may draw attention to your broader upper body and instead focus on accentuating your body with draped styles featuring a cinched waist. Don’t wear something you know is going to look unflattering on your body type, know what works best for you and stick with it. Just because it’s a date night and you’re expected to look more feminine than usual doesn’t mean you have to go out of your depth and opt for a fancy floral fitted number if this is not your style. Just stick to your signature style!

Read Also What Shoes To Wear With Jumpsuits

6. Don’t wear anything too revealing

Try and balance the line between looking overly va-va-voom or stick-in-the-mud conservative. Aim for a sultry siren meets girl next door vibe as this will give you the perfect amount of sugar and spice for that first date look. Don’t get me wrong, it’s great to show some skin, after all it’s a date. However try to limit how much you expose and keep it proportionally balanced. For example, if you’re going to go with an exposed side split you may want to ease off a deep V plunging neckline. Like a lot of my other pointers, this is a case where you want to think about the notion of less is more! Choose wisely what you expose as you may end up getting more than you bargained for when your date spends more time looking at your chest area while you’re speaking than your face.

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7. Don’t Buy A New Outfit, recycle an old one or better yet rent one!

The thing about first dates is you’re not always going to be guaranteed a second or even third date. It’s highly possible that the spark may sizzle out much sooner than you expected leaving you stranded with a one-time wear outfit. Let’s be honest, you probably will now have to shove it to the back of your closet where at some point in the future you will annoyingly rediscover it and be reminded of that guy that broke your heart. No need for me to go on any further, you get my point.Don’t buy it, rent it instead!Both your bank account and closet will love you for it.


  1. Don’t overdo it on the accessories. Try the‘less is more’ approach for a flawless end result. Sometimes all you need is a smile!
  2. Wear something that makes you feel good. We react better when we feel comfortable within our surrounding habitat. Two words ‘light and loose’.
  3. Be sexy without giving it all away. Appear more seductive than you may think by leaving more to the imagination. Show less and seduce more!
  4. Keep makeup fresh faced. Wear the appropriate makeup. Think natural look for daytime and slightly darker makeup for an edgy night time look.
  5. Dress for you. When you feel your best, you are your best. Make sure you are ultimately pleasing yourself first with your overall fashion look!

For more tips on how to style yourself date pretty read our Date Night Makeup Ideas blog post.


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