A Gentleman’s Guide for Men's "Night Out" Looks

Updated: Jul 14

Whether you’re going “out-out” for a session with the lads or a civilised cocktail or two with a special acquaintance, we’ve assembled some top style tips to ensure you look your very best.

So we’ve given you style tips on what to wear to a wedding and an interview. But now it’s time to think about a night out on the town.

Before you can down a few cheeky Jägerbombs or slowly enjoy a freshly poured cold pint, it’s important to get your outfit selection right.

And when your mind is firmly set on a fun night with your friends or loved ones, picking out clothes can often feel trivial.

That’s why we thought we’d put together a few considerations and top tips to prep you ahead of your next outing.

So let's get going on those men's night out looks, shall we?

Why your look is so important

When considering an outfit for a function or works do, you are under a lot of pressure from peers and partners to make sure you are appropriate for the event, as well as outwardly portraying yourself in a way that is fashionable and fitting to your character.

There is often a difficult boundary between making the right impression and overstepping the delicate line.

To make sure this balance is kept, keep in mind the following:

  • Don't be overambitious and buy a completely new outfit - you often haven't done a test run in this new look before and it might not be as flattering, comfortable, or fashionable as you think - instead purchase one or two new items which already compliment a staple piece from your own wardrobe.

  • Shape your outfit around one or two statement makers - small touches can lift an entire look a bold tie/bowtie, braces, pocket-watch, or shoes can add just enough extravagance to make an impression without overdoing it.

  • Make sure you are classic - It's always great to step outside of your comfort zone when it comes to fashion but remaining with classic cuts and styles will never go out of fashion. Some functions demand a fashion leader, not a trendsetter!

  • Be careful with prints - A printed shirt can really elevate a look, but make sure that if you are using prints to not over-do-it, it's important not to combine a print with loads of other bits and bobs, as it can come across as fussy and messy - keep everything surrounding the print clean and classy.

  • Finally - dress from the feet up! A lot more focus than you realize can fall on your footwear with women stating "you can tell a lot about a man by the shoes he wears" and bosses having admitted "If the shoes are scruffy and cheap, it lowers credibility and can give off a bad impression of a lack of care"

Location, location, location

Before you rummage through your wardrobe or head to the shops for a fresh tee, you should always think about the location of your night out and cater to that night's outlook accordingly.

For instance, wearing a t-shirt, ripped jeans and pumps just won’t cut it if you’re heading to Mayfair in London, while a blazer and smart shirt might look a little overkill if you’re just heading to your local beer garden.

A quick and dirty tip is to check out the website of a bar or club. If it’s littered with offers and themed nights, casual clothing is perfectly acceptable.

However, if the menu contains expensive cocktails or doesn’t have ‘ding-ding’ food on the menu (aka microwave food), a blazer/smart shirt and shoes are ideal.

Do what the ladies do! If you are lacking some crucial information about the event, speak to others in attendance, try and find out what their take on it all is - if you have a fashion-savvy friend, hit them up for some free advice on what would be appropriate.

These boots are made for walking

One of the main things to consider before a night out is your choice of footwear. Just think, you could potentially be on your feet all night. Whether that’s flagging a taxi, walking home, stumbling to the kebab shop, throwing a few shapes on the dance floor, or frustratingly waiting to be served at the bar.

For starters, here’s a rundown on shoes and their practicalities:

  • Loafers – a summery choice and easy to slip on when drunk. Suited to fancy clubs and cocktail bars. Avoid wearing them to bars or clubs with sticky floors, or you could end up walking around shoeless. Even though loafers have become popular recently it doesn't mean they are tailored to every outfit - a loafer is still perceived mostly as a casual shoe, but should you be pairing them with a rolled trouser they draw more attention to your footwear choice.

  • Trainers – ideal for casual looks to the pub, late night clubs and chain bars. However, if you’re going for a white pair, remember drink spillage could be catastrophic. Although trainers have been elevated recently to a more fashion-forward choice and their comfort has a lot to do with that; a trainer is still a sporting choice and can let down an entire outfit if paired incorrectly with a smart/casual look.

  • Chelsea boots – suited to every venue, minus the pub. The best part about Chelsea boots is that you can simply wipe away any muck picked up after a night out. The variants available for Chelsea boots are vast ranging from casual to formal, however, a boot is only worn with a suit if the wearer is extremely confident with their overall demeanor and is a rather ambitious choice.

  • Oxford shoes – the number one choice for any gentleman. These should only be worn for cocktail/restaurant nights and high-end clubs. They’re probably not the best if you plan on walking miles. Conventionally for smarter occasions, an Oxford or Brogue will give a gentlemanly and dapper appearance, make sure your location fits with these classic choices.

  • Chukka boots – the perfect cross between smart and casual, therefore making them useful for any occasion. But if they are made out of suede, be very aware of stray drink spillages and heavy rain. Chukka's trend to be simple in design and construction, if you are looking for something more "statement-making" I'd steer clear of a Chukka.

Looking to impress? Find out what shoes women find most attractive on men in our previous post.

Think ahead

We all have spontaneous nights where one casual drink down the local ends up with you trying to flag down a taxi outside a club at 6 am.

But if you can, and that’s a big but, try to think about what kind of night you are planning on having and especially if you will be moving on after your function.

Every city or town will have different types of places to have a night out in. From sophisticated cocktail joints to dingy clubs to rave in.

Here’s a quick guide on what to wear in every scenario:

  • Fancy club (think Mahiki in Mayfair) – chukka boots or Oxford shoes, blazer and/or tailored shirt, smart jeans, and a silver watch.

  • Standard club (think Popworld or standard chain club) – Chelsea boots or block colour trainers, ripped jeans, and checked/flowery shirt.

  • Rave (think Rainbow in Birmingham or late night club where you stick to the floor and have a banging headache the following day) – loose-fitting t-shirt, comfortable shoes (like trainers) and stretch slim jeans (so it’s easy to jump around).

  • Pub (think Weatherspoons or generic ‘Dog & Duck’ style pub) – a bomber jacket, pumps, jeans, and simple t-shirt will suffice.

  • Dinner out (think Turtle Bay/restaurant turned cocktail bar) – chinos, shirt, and boots will keep you looking smart for food, but give you the option to go rouge afterward if you want.

Whatever you do, for a perfect men's night out look - just remember to think location, shoes, and type of night. Once you establish this, you’ll be able to put an outfit together in a matter of minutes – which means more drinking or socialising time (woo!).

For more fashion and style tips, take a look at the rest of our blog here. Or access our full range of Men's footwear.

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