It doesn’t matter whether you’re taking your potential love interest out on a date for the first time, or whether you’ve been dating the same person for years, nailing stylish and fashion-forward date night style is essential.

Date night dressing is tricky, because you need to balance across the tightrope thin fine line between being too formal and too sloppy.

A full three-piece suit will look far too formal for a casual dinner or drinks in your favorite bar, whilst turning up in sportswear or your favourite sneakers will make it look like you don’t care enough to make an effort.

So what should you wear for that tricky first date? Here are our top tips and do’s and don’ts for date night style:

DO Keep Things Simple

The perfect date outfit will highlight your best features, whilst being fuss-free enough not to distract from your winning personality. Keep things simple but stylish, and pick just one key fashion-forward piece to show off your credentials as a future style icon.

Simple doesn’t have to be boring: simple simply means understated but effective. A plain blue button up shirt will highlight your killer blue eyes, and a fitted white tee will draw attention to the time you’ve spent in the gym this month. These low key pieces will make a much bigger impression on your date than wearing a loud Hawaiian shirt or clashing shades of neon; whilst these pieces might ensure you are remembered, you probably won’t be remembered for all the right reasons!

DON’T Wear Shorts 

Unless your date is taking place on the beach, or involves enjoying a vigorous exercise class together, you should never wear shorts on a date. Shorts look too informal, and create an air of indifference. When you wear shorts on a date you are showing the person you’re trying to impress that you have made minimal effort, and that you simply don’t care about your appearance.

That doesn’t mean that shorts can’t look good, and there’s certainly a time and place for wearing them. We particularly love the shorts and soft loafer combo demonstrated so admirably above. But the time and place for showing off your pins is certainly not on a date if you should be dressing to impress!

If the weather is too warm for full length pants, or you want to nod to the versatility of shorts in your outfit then why not consider opting for an ankle grazing chino or cigarette pant instead? These trousers are perfect for rolling up a little so that you can enjoy a romantic walk along the beach without getting sand in your cuffs, and they also nod to a more laid back and summery aesthetic whilst still looking date ready.

DO Choose a Leather Jacket

A great fitting jacket is a date essential, no matter what you’re doing. A blazer will look great, but a leather jacket will look even better. Nothing exudes understated masculinity, elegance and sex appeal quite like a leather jacket. The right leather jacket can make any man look like a bad boy, and this versatile piece can be worn anywhere and with anything.

For a casual or active date (such as drinks in your favourite bar or knocking down some pins at your local bowling alley) try teaming your jacket with a simple fitted tee and your favourite jeans, as demonstrated so admirably by David Beckham. For more formal dinner dates, throw your jacket on casually over a fitted button up shirt, tucked loosely into slim-legged chinos.

Choose a jacket that fits snugly across the shoulders and sits above your hip: looser and longer jackets look dated and old-fashioned. They also do nothing to show off your physique. If you’re looking to update or replace your leather jacket, then here are some of our favourite new season designs:

DON’T Wear a Suit

We know that you look great in your favourite fitted suit: everyone looks good in a suit! But a date where you’re trying to show off your natural and charming self is not the right time to bring your business face to the table.

This isn’t a job interview, or a convention, so leave your suit at home and opt for something more casual and full of your real personality instead.

If you are taking your date to a more formal event where suiting would be appropriate (an evening at the theatre perhaps) then opt for a navy blue or textured suit, to help differentiate between your more traditional black or grey business suit.

You should also wear a darker shirt and leave the tie at home, to create an evening look suitable for the occasion, that looks nothing like the suit you normally wear to the office.

DO Wear Your Best Watch

When it comes to accessorizing, the options for men are much more limited than they are for women. However the one thing that every man can wear with any outfit is a show stopping and attention grabbing watch.

A good watch shows that you are a detail oriented individual that cares about looking your best (and being on time) and is also a great way to show off your commitment to your favorite designer brands.

No matter what your personal style or how successful you are in your chosen path, there is the right watch for everyone.

By wearing your watch on your date you are offering a tantalizing glimpse into your life, and your personality and a watch is a great way to add interest and style to an otherwise straightforward outfit.

We love watches because they suit everybody: they are the accessory for the every man. Whether you choose a metal strap, leather strap, or even a sporty rubber strap, you should always choose a metal face with plenty of hardware to show off your credentials. Here are some of our favourite watches available right now:

DON’T be Too Flashy

There’s nothing wrong with a well-placed signet ring or a subtle bracelet or two. But when it comes to male jewellery, less is definitely more and a little will go a long way. This is particularly true of wearing jewellery on a date.

Too much jewellery can look flashy and be overpowering. Your date may be so distracted and dazzled by your bling that they forget to take the time to notice your dazzling personality as well!

Most people find someone who is flashy, or keen to show off their money a huge turn off (word of warning: the women not turned off by this are probably gold diggers!) So keep your flash tendencies in check, avoid wearing too much jewellery, and let your date get to know you for who you really are, not for how much stuff you have!

DO Have Great Hair

If you know that you have a hot date coming up then you have no excuse not to visit your regular barbers and have your hair trimmed so that you’re looking at your very best.

The best time to do this is two or three days before your date so that your hair has time to spring back and settle into its new shape.

On the morning of your date, wash your hair and then style it as usual: having a little product in your hair when you come to style it just before your date will give it texture and make it more manageable.

Hair with a little product in it also tends to look and feel thicker and will hold it’s shape much easier. This routine will work just as well whether your hair is short or long.

The fact is that, after your smile, your hair is one of the first things that a new date will notice. Taking a couple of minutes out of your day to ensure your hair is looking its best could be the difference between a bad date and a great one.


The most important thing that any man can do on a date is be himself. If you’re being true to who you are then your personality will shine through and sparks will start to fly regardless of what you’re wearing.

However initial attraction is a very important part of choosing whether or not to head out on a second date, and your fashion choices will be integral to this.

The key to great date style is to keep things simple, look like you’ve made an effort and dressed to impress without trying too hard, and ensuring that elements of your personality are still able to shine through.

Don’t overthink what you’re wearing, ensure that everything you put on is comfortable (the best way to do this is to ensure you’ve worn everything you wear on your date before) and above all else, go out and have fun!


recommended: Men’s Brunch Outfit Guide (For a Date or Meeting With Friends)

The post Do’s and Don’ts For Date Night Men’s Style appeared first on Royal Fashionist.


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