What to wear on a first date – Dating Expert Advice

Many dating coaching clients are unsure about what to wear on a first date. Good first impressions on a date are crucial if you want the best start possible. Turning up to a dinner wearing trainers or slipping on your most glam LBD and stilettos for the cinema can make for an awkward beginning, so dressing for the occasion is the first important step.

The majority of first dates happen over dinner or drinks, normally a more upmarket restaurant/bar in a nicer part of town (hopefully!), so something smart/casual is ideal.

Advice for Men

If you are a guy, it’s simple; a non fussy, IRONED shirt and smart dark jeans work well as a general guide.You need to keep to block colours. Hawaiian, paisley and bold eccentric prints should never be an option for a first date. When she gets to know you more you can start bringing out the show-stoppers.

Woman will mostly notice and make judgement on footwear so choose a wise match for your outfit. If your shoes are scuffed after 30 drunken nights out on the town, they are a no-go. If you are in love with your new bright red Doc Martins, those too are a no-go, at least for a first date. Simple boots or casual shoes are perfect in a neutral tone which compliments your clothing.


To wear a tie or not to wear a tie? Indeed that is a good question. Some would say yes, I say no only because it can seem like you are trying too hard. You want to make a great first impression but it has to look cool and natural, like you haven’t tried at all; you just happen to look great all the time! Keep ties for the boardroom, unless it is a formal affair. The only accessory you need is a nice watch and belt.

Advice for Women

For women, it’s much more complex when it comes to choosing what to wear on a first date. There are just so many more options. I have female dating coaching clients who have spent the majority of their day deciding what to wear and how to do their hair, among booking manicures, waxes and keeping an hour aside for make up alone. One even went as far as to cancel a date because she didn’t feel her outfit was right.

I’m going to break it down to simple do’s and don’ts  of what to wear on a first date : 

First off the leg/boob rule:

If your going to show one you CANNOT show the other. This is vital if you want to be taken seriously. The saying “if you got it flaunt it” is true to an extent but choose one area and cover up the rest. You want to feel confident so show off your best asset.


Skirts VS trousers: In general men definitely prefer more feminine outfits. A tight but non-revealing dress is perfect if you have a good silhouette. V-necks and scoop necks work well on longer dresses and high necks on shorter. A soft, shear blouse is also nice tucked into a mid-length skirt teamed with sexy heels. If you’re more of a trousers girl go for a tailored, bum friendly pair or dark tight jeans teamed with heels or boots.

If you’re less booby, a small low cut top and oversized blazer looks great with jeans.

As for hair and accessories, keep it very simple: less is definitely more. A nice pair of gold hoops, a stylish watch and hair warn out and effortless is enough to make a statement.

On the whole, my main advice I would give to both sexes is to be yourself but keep it safe. You want your winning personality to be the main focus on the date, not a bad choice of outfit.

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