How to Look Effortlessly Cool on Your First Date

Master the art of effortless cool with Amanda's guide on what to wear on your first date.


So you’ve got a hot date and you want to make a great first impression. One of the first things your date is going to notice about you are your clothes, and striking that delicate balance between ‘I couldn’t care less’ and ‘I put way too much effort into getting ready’ is a fine art.

If you’re dating a younger woman, the look you want to go for is ‘effortless cool’. This is a surprisingly easy look to pull off; all you need to do is take your existing style and make a few minor adjustments. Follow this guide and you’ll have no trouble figuring out what to wear on your first date.

Dark Denim Does it Best

Jeans are the single most versatile piece of clothing that we have today. With many designer jeans going for hundreds of dollars a piece, it’s safe to say that denim jeans have established a firm foothold in smart casual style.

Go for a basic, dark shade of jeans and avoid stone washed or torn jeans on your first date. Find a slim cut that suits you and wear them in at least a week before the date. It’s easily to tell which guys are trying on skinny jeans for the first time and believe me, wearing jeans that restrict your circulation is a very bad idea if you’re looking to make a good first date impression.

Don’t even consider wearing khakis unless you’re over 50 and your date’s at the local country club.

Think Shades, Not Colours

Once you’ve decided on the colour of your jeans, consider a lighter shade of that same colour for your shirt. You can’t go wrong with a neutral shade like dark grey or white. Remember, the fitter you are, the lighter the shirt you’re going to want to wear. Darker colours help to hide love handles and make fit guys look smaller.

If you’re looking to dress it up a little, buy a fitted shirt that you can leave tucked out. If you find that you look a bit too formal, unbutton the cuffs and roll your sleeves up.

If you’re going for something a bit more casual, try a snug crew neck or v-neck t-shirt to go with your dark denim jeans. The simpler the better – avoid t-shirts with loud designs and stay away from primary colours unless you want to look like a little boy.

Don’t Be Afraid to Accessorise

Accessories like shoes, belts, watches and cuff links are a great way to add character and personality to your outfit. Spend the money on a nice pair of shoes and make sure your wardrobe has at least two belts; one brown and one black.

Accessories are also a great conversation piece, so don’t be afraid to wear something unique that you can tell a story about.

Make it Your Own

I hope this guide has given you some ideas on what you wear on your first date. Remember, style should be something personal. Looking like something lifted straight out of a fashion magazine might sound like a good idea in theory, but chance are that you’ll end up looking just like the guy who came before and the guy who’s likely to come after.


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