Men's Holiday Style Guide 2018: Essential Items and How to Make Them Work for You

Men’s Holiday Style Guide 2018: Essential Items and How to Make Them Work for You

Men’s Holiday Style Guide 2018: Essential Items and How to Make Them Work for You

So, you have your 1st holiday or getaway booked for this year, you have been bombarded with list upon list of things everyone else needs to go away (and seriously can’t leave the house without), you are full of requests to get money exchanged ensure passports are right and everything is packed, including the kitchen sink. You know if you take a big bag it will be filled with a load of your partners kit that ‘just wouldn’t fit in her case’ and don’t necessarily have the time or desire to trawl the shops or internet for loads of clothing, bags and accessories. Our Mens Holiday Style Guide 2018 is here to answer all your questions.

This guide aims to take the stress out of your packing so you can get to the airport or nearest motorway without going completely insane! It also mean’s you won’t look like a tramp on the beach or, even worse, a middle-aged bloke with a vest, budgie smugglers and a sandal/ sock combo!

Depending on what your trip consists of there are a few select pieces which can make you look good and be a staple for your wardrobe for the full summer.

To make sure you have the best information to give you the easiest life we have split this article into sections which help you pick out what works for you for each item.

The top essential items and how to make them work for you:

  • Shorts
  • T-shirts
  • Shoes
  • Flip-Flops/ Sandals
  • Sunnies
  • Hat’s
  • Watches
  • Underwear and Socks
  • Eveningwear

Men’s Holiday Style Guide 2018: Top Essential Items and How to Make Them Work for You


So, shorts are an easy pick, if you are a 6’3″ gym goer with muscles on your muscles. However, for the rest of us mere mortals, the selection of shorts can be an absolute bloody minefield. We’ve all seen the pasty white chicken legs in ill-fitting shorts or the absolute eye burning sacrilege of watching someone squeezed into a pair of old shorts that they just haven’t admitted don’t fit anymore!

Beach Shorts or Swim Shorts

Look, budgie smugglers are just not acceptable. Ever! Leave them in the 1970’s where they belong! So if you are looking for a good beach short or swim short then in 2018 shorts are getting longer again, not to the extent of late 90’s early 00’s big board shorts but they are getting longer again.

There is an easy rule of thumb to know though and it all depends on your legs. If you are very well toned with ‘footballer’s legs’ then go for a set of short shorts, if you have thigh’s worth showing off then go for it! If you find a good pair of swim shorts you can wear them throughout your day on the beach, both in and out of the water.

If you have legs that, well . . . you know, then a slightly longer short is advantageous. It give’s you a little more coverage and helps to avoid ‘chicken leg’ syndrome. It also helps to make a larger ‘dad bod’ belly look less prominent if you are going topless.

Dress / Evening Shorts

So, what do we do? Well, the 1st rule of thumb is ditch ANYTHING with more than two pockets. In 2018 if you want to wear a more ‘formal’ looking pair of trousers then something simple in a muted colour will work perfectly with the rest of your wardrobe and be a useful piece for the whole summer. Cheno Shorts are definitely in.

Just a thought on your legs!

Look, if you have had your legs tucked away over the winter for 6 months they are going to look terrible if the 1st time you get them out is on the beach. Let’s face it, no one wants to be seen rocking the anaemic ‘I’ve just got out of a full leg cast’ translucent look. So if you know you are going to be going away then make sure you get those legs out early and start hanging out in the garden on any day when the mercury reaches over 10°C.

If that’s not possible then there is always a light, gentle fake tan. Just make sure it goes on even or you will be able to hear the sniggers as you walk.


T-shirts fall into two main categories for men. Simple, understated and plain or wild patterned/ logoed and out there. However, I guess we should first concentrate on the one big ‘don’t’.

Just Don’t!

T-shirts are not a substitute for a sense of humour! We don’t care how much beer you think you can drink or what you want to do to some ‘lucky lady’ later. Seriously, if you think ANY comedy t-shirt is funny then just don’t. T-shirts of this ilk are never funny and are the beach/ holiday equivalent of the comedy tie at work. Seriously, try wearing one and look at how your colleagues automatically start to avoid you. Well, it’s the same with these t-shirts, they simply scream ‘knob head’ to everyone around you and cut the chances of meeting some random holiday friends to 0!

Now that’s out of the way let’s talk about what does work.

Plain and Simple

A plain, but bright, understated t-shirt will work for anyone, it doesn’t matter what age or body type a crisp plain look with project an effortless style while also being very easy to match up with other clothing and accessories you might wear. As long as it’s clean and ironed then you just can’t go wrong with a plain T.

However, a plain T-shirt doesn’t have to be boring, pocketed styles are becoming increasingly popular again and give a bit of a focal point to the top and also ‘shorter sleeve or roll up’ Tee’s are great if you have a decent set of arms, they can also help give you a bit of shape if you have decent muscle mass but aren’t exactly toned, a darker shade is really great for this but lighter colours work too.

Go wild

We all love a patterned or branded t-shirt, they are a great way of showing the type of person you are or what you might be in to in a very stylish way. However, over the last year or so, big patterns and wild multicoloured looks have also come in with a vengeance, and this year is no different.

If you keep the rest of your outfit quite ‘block coloured’ then that wild or patterned t-shirt can make a great statement piece for your outfits.

However, one note of caution. If you are a ‘bigger’ gentleman then a very strong pattern may make you look a little rounder than usual so if you want to introduce pattern and colour then a good branded t-shirt will be a far better option.



The shoes you take away with you are probably the most difficult things to plan for. They are such a bulky and relatively heavy part of your packing making sure you get the right shoes which can work as evening wear, as well as day wear, is key to keeping your bag weight down while having a style of shoe which works in every situation.

With this in mind, there is only one real solution. A soft pair of plain ‘tennis shoes’ can be worn with your shorts during the day but will also not look out of place under trousers while out for the evening.

Flip-Flops / Sandals

Your flip-flop choice is probably one of the biggest decisions of your holiday, if not your life. Well, maybe not but I do love my flip-flops so maybe it is for me. There is one fundamental decision to make when choosing your flip-flops, and it’s all about what you need them for.

If your main need is for something to pop on and off whilst getting in and out of the water and for keeping the sand off your feet for short walks between your hotel and the beach then go for a flip-flop with a ‘slider’ upper or rubber based toe strap. These will ensure ease of use and something which will dry quickly and easily around your wet feet. However, the compromise here is that if you are out all day walking around they can become a little uncomfortable.

If you want to be out and about all day, walking around and taking in the local scenery and culture, yet want to have the joys of the cool breeze at your feet and a comfortable flip-flop then looking for something with a textile toe strap and an ergonomically designed footbed is essential.


Choosing your sunglasses has everything to do with the shape of your face and what suits that shape. You can then choose which type you like based on which styles suit you best.

For more information on this check out our full sunglasses guide here:



So, the hat you choose to wear on holiday is a very personal decision. To be honest, unless you are out in the full heat of the midday sun, like mad dogs and Englishmen like to do or are going a little thin on top then hat’s aren’t really a ‘holiday essential’.

If you do decide to take a hat then a fedora is a little dated, floppy cloth hats, Panama’s and straw hats shout be approached with extreme wariness, but are not out of the question. It really depends on your age or how ‘hipster’ you are.

Far better to keep it simple, a good flat cap or baseball cap gives you the sun protection you need without looking too ‘scruffy’ or ‘try hard’.


When it comes to a holiday watch, any sensible traveller, unless they are away on a business trip, need to follow these two simple rules.

  1. Don’t take something too expensive, the whole point of a holiday is to relax so what’s the point of having some £2k watch which makes you terrified of scratching it or even worse, losing it in some way. You are far better to take something which looks good but is designed to be worn outside and can take the abuse that jumping in and out of the water will cause.
  2. Wear a strap which isn’t going to open up at the worst possible moment. A good quality ‘action strap’ is something which is often overlooked. If you are going to be in and out of the water or doing sporty activities then a suitable, waterproof and strong strap will make sure your fun days don’t end in searching for a lost watch you will never find.

Underwear and Socks

The 1st rule of looking good on holiday is ‘never wear sandals and socks’. The 2nd rule of looking good on holiday is ‘NEVER WEAR SANDALS AND SOCKS’! Seriously, what do these people think, who is telling them it’s acceptable? Are these people locked in a box for the rest of the year with no contact with the outside world and just wheeled out for everyone else to laugh at whilst on holiday? I just don’t understand!

When it comes to underwear, during the day its one of the few times in your life it’s acceptable to ‘go commando, that’s wearing no underwear to anyone who hasn’t heard the phrase. This does, however, have a caveat. This is that it’s only acceptable if you are wearing beach or swim shorts if you are wearing a dress short or evening trousers a good pair of clean and comfortable boxer briefs will be both comfortable and keep you cool and dry.

When it comes to socks there is only one option, if you are wearing a soft shoe or trainer then a set of low cut ‘invisible’ trainer socks. Not only will they help you keep cool on a warm evening but they will also make sure you don’t look crazy with a big pair of socks hanging under your dress shorts or trousers. The only time a pair of shorts is acceptable to wear with long white socks is if you are going for the ‘Cholo’ look, however, that’s a pretty hard look to pull off unless you have a bald head and lot’s of gang tattoos to go with it.


When it comes to eveningwear then the keyword is ‘relaxed’, that still doesn’t mean you can start wearing linen suits, but it is definitely a philosophy which holds true.

For more information check out our ‘Streetwear’ section on the blog below:


Well, there you go. Our comprehensive guide to getting your style right while on holiday in 2018. All you need to do now is book your flights and get going! If you would like to know more or have any advice or comments of your own then don’t hesitate to get in touch with us through the comments section below. Happy holidays!





Ian Hughes

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