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Date Night Dressing: How To Keep It Cool & Casual

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The Gentlemen’s Curb

It’s The Gentlemen’s Curb a lifestyle blog where fashion meets fitness in a BIG way. Our blog is centered around men of size, big and tall men, but there is something here for everyone. We are back to doing our best to share some information with you.

Date Night Dressing: How To Keep It Cool & Casual

First dates are always stressful. There’s never going to be a time when first dates aren’t stressful. Even if you’ve known the person who you’re going on a date with for a while, it’s still going to be a little stressful. The truth is that first dates are all about making a good impression, which is what makes them such a stressful process. When it comes to preparing for a first date, often the most difficult part of the process is choosing what to wear. Naturally, you want to look (and feel) your best, which is why knowing what to wear is so crucial. Today, the key to fashion success on a first date is simple: dress to look cool and casual without looking sloppy. While that advice might seem simple and straightforward, choosing what to wear is not always as easy. Bearing that in mind, below are some fashion tips for making it easier to select what to wear on a first date.

Avoid ‘smart’ trousers

Today, the dating world has changed significantly. Dinner dates used to mean wearing a suit complete with a tie, but today that’s rarely the case. Unless you’re taking your date to somewhere exceedingly posh, you can probably forget the suit and tie and the smart trousers too. It’s far better to opt for a more casual trouser, such as a smartly cut skinny jean (rip-free, of course) or some Kahkis trousers – Bills Kahkis have a wide range of suitable designs to choose from – and pair your trousers of choice with a smarter top.

Keep your shoes casual

Don’t make the mistake of pairing casual trousers with smart shoes, it really doesn’t work. Instead, opt for semi-smart shoes or trainers that are clean and well-designed. Choose a shoe that works perfectly when teamed with your outfit; what you don’t want is a shoe that makes your outfit look too casual. You want to opt for a shoe that is the perfect balance of cool and casual without looking sloppy or making your outfit look sloppy.

Get your top half right

There are ranges of options for your top half. You could opt to team a polo neck top with an oversized blazer – this look works well with black skinny jeans – or you could pick out a simple t-shirt – a polo shirt is probably best though as it is casual with a smart edge to it. In colder weathers, wearing a cable knit sweater could also work well. For a smarter look, you could top this off with an oversized blazer with rolled sleeves.

Coat or no coat?

Depending on the weather, you may want to wear a coat. If you don’t, ensure that your outfit looks chic without it. If you do, make sure to choose a coat that compliments your look and enhances it further. Never wear an overly smart coat with a more casual outfit as it can end up creating the illusion that your outfit is sloppy and you haven’t put time into choosing what to wear, which translates to – ‘I have made no effort and don’t care’. Always pick a coat that works perfectly with the outfit that you have picked out.

There you have it, a guide to date night dressing and keeping your look perfectly cool and casual.




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