First impressions count, and one of the most important first impressions is a first date. Can what you wear on a first date make the difference between whether or not you secure a second?

Linda Prescott - Director of Ideal Introductions 1


Ideal Introductions’ Linda Prescott

Dating guru Linda Prescott thinks so. As a professional mach-maker and owner of dating service Ideal Introductions, Prescott is experienced in the area and says when it comes to what to wear on a first date, there are no second chances as to the impression you create on your potential new partner.

“It’s always better to be overdressed than underdressed,” says Prescott.

“People often confuse ‘good looking’ with ‘looking good’ and people are actually more attracted to people who look good as opposed to them being good looking, as this can be quite intimidating on a first date. It all comes down to making the most of what you have.”

Here’s a few key tips to get you started:


  1. For a daytime date, chinos and a short sleeve button up shirt always a smart look. If it’s more casual, choose a short sleeve button up shirt undone, with a nice plain white tee underneath. Match this with a pair of smart casual shoes and ankle socks – this is a great look for all ages. There’s also the option to wear a smart polo shirt if it’s a hot day.
  2. It is really important to try and look modern.  A lot of men keep things in their wardrobe for years and years. My advice is to de-clutter and purchase some new items which you can mix and match.
  3. Classics always work. Brands like Ralph Lauren and Country Road won’t date. In making a nice first impression, I always think plain colours or classic prints work better than busy patterns.
  4. If you’re going out for dinner, my suggestion is always a long sleeve button down shirt, dress pants or possibly a smart pair of denim jeans, depending on the venue.  Also match your belt with your shoes.  Women will always check out a guy’s shoes so make sure they are clean and on trend.
  5. No bracelets or necklaces, please. Women don’t really like jewellery on men except for a ring and watch.
  6. Never wear thongs or sneakers no matter how dressy or trendy they are! If women don’t think you can make an effort with how you dress on a first date, they will come to the conclusion you probably won’t make an effort with anything to do with the relationship. Hard to accept, but true!


  1. Men like feminine ladies.  That doesn’t mean you have to be a complete “girly girl”, but they want to feel like they are dating a lady and that you have made an effort to impress.
  2. Always wear make-up. Even if you prefer the natural, the rules are different on a first date and lip gloss foundation and mascara are a must. No exceptions!
  3. I’m of the belief women should always wear a dress on a first date, using the same rule which applies to men – classic prints, nothing too busy.   And always remember this – if you can see up it, down it or through it, it is definitely not appropriate.
  4. If you have a nice figure, show it off in something that is reasonably fitting.  But never wear lycra.
  5. Curvier ladies can look fantastic when they dress for their shape. Research which cuts suit your figure the best.  There are many great websites providing tips on styling, and if don’t have time to shop for yourself, employ a stylist to help you out!
  6. I believe in heels for an evening date, but not too high or difficult to walk! You don’t want to be falling on your face on the first date! For the day time, wear ballet flats or a cute pair of dress sandals. Once again no thongs – even if they are Havianas!


  • Always make sure your hair is freshly washed, cut and/or coloured.
  • Smell good! Aftershave or perfume a must – if nobody has ever commented on the one you usually wear, maybe it is time for a new one.  If you have no idea where to start ask your shop assistant and they will be able to guide you.