Dating Advice

What To Wear On A First Date


Styling Tips for What To Wear On A First Date to Guarantee a Second

What creates a positive first impression on a date?

So, you’ve been doing a string of first dates but find getting to a second, harder than mastering a Rubix cube? You could speak to a dating professional, to help tweak your dating experience. Small changes, however, to your wardrobe selection may help deciding what to wear on a first date.

Our greatest advice is… don’t take dating fashion tips from a bestie, unless your bestie happens to be a male fashionista and dating mastermind. We asked men about what they thought looked great on women and what creates a positive first impression on a date. Their responses differed significantly from those of women’s.

Why Styling for Dating is Different

So, you know your style and you have heaps of it! You dress appropriately for your age, body shape and even surprise yourself with the classy bootie you come home with on your budget. You were born to shop and are in the gold class of fashionable bargain hunters. You read fashion blogs and subscribe to fashion Youtubers, and have even thought about doing (or already do) your own channel on your styling prowess.

It doesn’t matter if you are a vintage shopper extraordinaire or Donatella Versace in the making, dressing for dating is a different art. Eric Wargo of the Association for Psychological Science warns that there are no second chances when it comes to making a first impression. In the past we thought we had around 60 seconds to create an impression, however new research reveals that it may take as little as a tenth of a second to make an impression, and longer exposure doesn’t significantly alter this impression.


What Men Wanted:

Fitted Clothing versus Flowing (non-fitted styling) – Answer: Definitely Fitted

Most men thought that fitted clothes were more appealing. They felt being able to see a woman’s figure attracted them more. This could be down to being unsure about a woman’s size under baggier garments. Of course, ‘fitted’ doesn’t mean lycra-tight and dressing inappropriately for your size and body shape. It means selecting thicker fabrics that hide imperfections and keeping the dress shape more slimline rather than slowing A-shape.


Our dating fashion tips are:

Particular times of the day or month may mean the difference between our favourite cream dress looking amazing or making us look like we’re just about to bloat right out of it. Follow the other styling tips for dating but still keep in mind that we need to choose an outfit that compliments how our body is looking on that particular day. I’ve often asked myself, why do I look thinner in the morning than I do at night. The very same outfit that I could look great in on a morning date may be a fashion serial killer that evening.

Dress for what suits your body type. Be selective and creative. Although we’ve just said ‘fitted’ is preferable, you can always have your sleeves fitted for example, and still have the torso part of the outfit a little more flowing (giving the impression that the outfit is fitted) or, ensure that the outfit is fitted looking in the bust area but flowing around the thighs to cover weak spots. Be cleaver and work with what you have as we’re not all born like Kate Moss but we can still work with what we have to our advantage.

Plain Fabrics versus Pattern – Answer: Plain

To increase your chances of a second date, men saw plain fabrics as being sexier than patterns, although this may depend on the pattern. Harsh patterns (bold coloured dots, like black and white and bold coloured stripes) were considered overpowering and floral prints may also be risky.


Our fashion tip around what men want:

If you are comfortable with non-print, plain fabrics, go for those – they may be a safer option particularly for those men who have more conservative taste. If you love prints, and don’t want to wear anything else on a date then go for something simple, like pale coloured prints or do prints in the skirt matched with a plain top etc.

Short versus Long Dresses – Answer: Short (but not too short)

In our survey, mostly the responses indicated that above knee length was good but no underwear-peeping-short. Just above the knee was seen as elegant as long as it was more ‘hugging’ and once again, not flowing resembling a nylon tent.

Our fashion tip to dating says that:

It largely depends, of course, on the type of date. If you’re going to the markets on a Sunday morning, then that would require something shorter and/or more casual looking, pants or a shorter skirt but only if you have the body shape to match, (please don’t otherwise). It all depends on the type of function and where you are going on the date. Laura Jerpi of The Art Institutes cautions that if you are unsure about the venue or dress code, contact your date for clarification or research for yourself where you are going, as there are seven different types of dress codes for all different occasions.

Dark Colours versus Pastels – Answer: Pastels

Black and other dark colours were seen as more unfeminine. If your date wears corporate garb all week, then he may be just a little over strong colours like black, French blue, brown and navy, maybe even other strong colours such as red. Wearing pale colours isn’t likely to remind your date of the stress of the work week or next week’s pending board meeting.

Our fashion tip to dating men is:

If you must wear a dark colour because you can’t contemplate anything else, then of course wear it. Depending on your man’s taste it may very well work for you. We simply talk here about hedging your bets and optimising your chances of making a positive first impression. So, if you don’t feel giving up your first-born child to don dark colours, then don’t. If you want to maximise your fashion choices for dating, then ditch the dark and enter the light.

Expensive Designer versus Off the Rack Cheap – Answer: doesn’t matter

Provided the outfit looks stylish and in good condition.

Our dress-for-dating-tip agrees. It doesn’t matter if you choose couture or made-on-a-home-sewing-machine masterpiece. As long as it matches with all the other criteria listed here, fits well and is pieced together masterfully.


Short versus Long Hair – Answer: Long

Long hair was definitely seen as hotter than short. Who knows … could be a cave man thing.

Our tips to dating:

Unless your hair grows like Rapunzel, you’re not really going to be able to do anything about this one at the last minute, however, it may be something you can think about for future dating.

Hair colour is also our other consideration. This will largely depend on your personality type. Conservative, natural hair colour is not for everyone. We suggest you have a firm idea of the type of person you are wanting to attract and match your colour choice to that particular person’s character. (ie conservative banker versus circus performer)

Less Makeup versus More – Answer: Less

Particularly for a day date, less turned out to be more. In addition, men assumed women wearing more makeup would take longer to get ready (irritating). Men liked women to appear naturally beautiful. Less makeup is more likely to show men you aren’t hiding your looks behind a heavy face of makeup.

Glenn Yeffeth, publisher of Benbella Books, recently quoted in Shape Magazine article: ‘What Men Really Think About Your Makeup’, “I think a lot of makeup actually makes women look worse”. Out of the 15 guys interviewed, the general consensus was ‘less is more’.

Our dating tip for what men want:

Unless you’re a Geisha go lightly on the palette. Men like to feel that their ideal partner is naturally beautiful and won’t scare the pants off them if you both end up on an episode of Survivor and your makeup bag is nowhere to be seen. So, go as natural as possible given the time of day and the event you are attending.

Cleavage versus More Conservative – Answer: Conservative 

A small amount of cleavage was OK provided it still looked conservative and tasteful. Cleavage and short length dress together were seen by men as someone you would take home and perhaps date but not necessarily marry. Food for thought.

Our tip for dating:

Be careful with showing too much cleavage until you know the person well enough. Some men love partner’s showing cleavage but others strongly feel that cleavage-Clair is not who they will want to take home to meet Mum and Dad.

Right for your Body Shape and Personality

Responses aside, the single most important tip for dating styling is to accommodate your own body shape and personality. If your legs aren’t your best feature, go long or you have a camel-nose cleavage, perhaps leave it under cover. Critically analyse both your worst and best features and plan your wardrobe around these. Fashion says a lot about who we are and therefore should be matched to that. We need to ultimately feel comfortable in how we present ourselves. This impacts heavily on how we will ultimately act during the date which could turn out to be Cameron Diaz chic or Amy Farrah Fowler dreary.


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