How To Dress For A First Date

They say first impressions are vital when it comes to meeting someone for the first time, and first impressions are often made upon how you look.

Therefore in today’s guide, we want to make it easy for you, breaking down some key looks you can wear for a variety of first date occasions.

Before we dive in though, looking good is just one part to a successful date. Therefore we’ve got some additional tips at the end of this article for you to consider…

The Bar

The typical first date is often in a bar for some casual drinks; with alcohol flowing it’s often a date that turns awkward silences into intoxicated personal conversations pretty quick.

The location and dress codes of the bar play a huge part in what you should wear, so do your research before turning up. If you don’t know, it’s better to overdress than underdress.

Keep a balance between smart and casual, as to formal could leave your date feeling undressed and it can also make it look like you’ve just come from the office.

dressing 1

Add individual touches through the use of accessories to add detailing to your look, and accessories can also become conversation starters… (“I like your watch, where’s it from?”)

borg collarhaig jumpercanali button shirts

cotton poplinejack purcelldaniel wellington

The High End Restaurant

This is where you need to dress to impress. If you’re treating someone to a high end, expensive restaurant then they’re going to be spending time on how they look… you need to do the same.

A suit is your friend in this situation, but don’t go for a too ‘corporate’ look. Add in some effortless elegance, such as losing the tie or wearing separates over a full suit.

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Trying to hard can leave you looking like this way of dressing is out of your comfort zone. You need to look good, but feel comfortable.

martin blazerscurved shirts

hounds trousersbrown ellery

The Cinema

A classic choice, but something we don’t recommend. How can you get to know someone when you have to sit in silence watching a film neither of you probably wanted to see in the first place? Leave the cinema for a couple of dates…

Keep your attire casual, but wear at least two formal items.

Choose from the following:

  1. A Formal Pair of Shoes or Boots (Brogues, Monk Straps, Leather Chelsea Boots, Oxfords)
  2. A Tailored Pair of Trousers
  3. A Buttoned Down Shirt
  4. A Tailored Overcoat

Just choose two of the above, or you could be left look overdressed. Here’s an example…

edge nylon jacketfrost marl jumper

tight long jeansloake boots

Again, you need to feel confident with what you’re wearing. Be comfortable, and you want to mirror the effortless elegance of James Dean.

dressing 3

The Summer Date

If the sun is shining, a suit probably isn’t your best option. Sweating isn’t attractive, and wearing a suit to a first date on the beach isn’t recommended.

So dress it down, but don’t be scared to layer. If you opt for lightweight fabrics you’ll avoid overheating and by doing so you get to wear more to impress.

dressing 4

We’ve kept it simple with this look, pulling together some summer staples alongside a lightweight jumper in case your date gets cold in the evening.

extra fine sweaterpolo gucci shirt

wicker shortsbermuda shoes

Lunch (or a Coffee)

Same principles apply to the cinema date, keep it casual but add in some touches of formality.

dressing 5

The leather jacket is a staple which screams masculinity, and when worn with the right attire can have a massive impact.

porter bikersfrost marl tee

redford jeansred wing moc boots


In this video, we give you more inspiration as we break down some more key looks for first date scenarios.

How To Act

Lastly, the way you dress and look has a huge impact on how successful the date is. But looking good is just a small part to getting a second date.

Here are some things to consider.

Smile – Research shows that smiling makes you more attractive. It also makes you more appealing and easy to open up too. Remember to smile when you first meet your date, and also as the date goes on. Don’t fake it though… you’ll look like a creep

Eye Contact – Making eye contact is hugely important. When you talk to your date and make eye contact, it shows you’re confident, but when you make eye contact while they’re speaking it shows you’re interested. Too much eye contact is creepy though… so every now and then look down at your drink/food and around you slightly.

Concealing – Being mysterious will lead your date wanting to find out more about you. Let them do most of the talking, while you pull back them lugholes and listen. When it’s your chance to talk, show authority in what you say but don’t give everything away. Talk about yourself, and then shift the conversation back to them. This leads to your date being intrigued, wanting to know more…

Confidence – We recently made a video about ‘What Women Like In Men’ and the number one thing that came up was confidence. Take control of the date, and showcase confidence and authority. There’s a thin line between being confident and arrogant though, so tread carefully.

dressing 10

Take Control At The End – Pay the bill, and take control of the outcome. Did the date go well? You push forward with what’s going to happen next. Arrange a second date, invite them back to yours, head to another venue… you initiating the next step to shows authority and confidence.

So there we have it, your ultimate guide to what to wear on a first date. In fact, we’ve got you covered for what to wear for the first few dates if you get lucky…

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