A beach holiday? What will you pack?

That Dapper Chap looks forward to his holiday in the sun and tells us what we should consider packing in our cases.

So, you’ve waited all year. The vacation was booked months ago, you’d kind of forgotten what the place looks like, but now its only a month away and your excitement is renewed. But what are you going to take? Is it still okay to wear espadrilles? Will that Hawaiian shirt be okay to wear to the beach bar at night?  Well, I’m not going to dictate what you should and shouldn’t wear as we’re all individuals and can wear what the hell we want to but I can tell you what I’ll be packing and will hopefully keep it smart and dapper, even on the beach!

Classic white trousers and a pale blue blazer

It’s tempting to think “I’m on vacation, who cares what I look like” and throw a bunch of shorts and sleeveless T-shirts into a case along with a pair of tatty old sun shoes and to hell with it. But what about your reputation as a dapper gent? I’ll still be posting pictures to Instagram while I’m sunning myself on my much needed fortnight in the sun! So, pay a little attention to what goes in your case this year and with some careful planning you won’t need to cram in your entire wardrobe.


The first thing I’ll be packing are shorts. Chino shorts are great as they are light weight and look smart. You can roll up the legs and sun bath in them topless but still looking stylish in your sunglasses and straw hat or you can roll them down for night time, pop on a cool white linen shirt and a belt and a pair of smart brogues, ready for that tequila sunrise at the beach bar.

River Island beige chino shorts £25

A beige pair of chino shorts are classic and will look great with almost anything. I would wear these with a white polo shirt, a long sleeved patterned shirt for the evening or even a T-shirt for day time sight seeing. Add a pair of white canvas pumps during the day or leather flip flips and dress them up at night with brogues.

River Island printed shorts £30

I’m taking a few pairs of shorts in various colours and patterns, all classic looking with a tailored look like the ones below.

River Island pink shorts £30

Of course you’ll need some shorts to swim in. I’d recommend some in a plain colour or a floral print such as hibiscus or tropical print. Make sure they are short and are well above the knee. These look so much classier than the calf length versions and will make you look taller and leaner.

River Island £22.00

River Island £20.00

I usually take 3 or 4 pairs of swim shorts. If you’re on a beach or pool holiday it’s likely that you’ll be in them a lot as you’ll be in and out of the sea/pool a lot so take enough to be able to rotate them so you look fresh each day. Don’t forget to wash them out every night.


The other essentials are shirts and T-Shirts. I personally only wear plain T-shirts as I think these look classier than ones emblazoned with logos, football teams or pictures. Let people see you and not the T-Shirt. A plain T-Shirt never offended anyone but I’ve seen plenty of horrible printed T-Shirts that offend me!

For the evening and day drips when you want to possibly be covered up from the sun I’ll be packing a collection of long sleeved and short sleeved shirts in both plain and patterned lightweight cotton or linen.

New Look tropical print shirt £15.00
New Look cream linen shirt £18.00

Zara Bird print shirt £25.99

Image 2 of ELEPHANT PRINT SHIRT from Zara
Zara Elephant Print Shirt £25.99

A plain white shirt and chino shorts

What about long trousers?

I will also take a couple of pairs of long trousers just in case I need to protect my legs from the sun or go somewhere which dictates that flesh must be covered. I have a pair of loose navy linen trousers which I team up with a white linen shirt, white pumps and a straw hat. I’ll also take a lighter colour pair, maybe beige or white.

A classic look

Add a linen jacket for evenings to keep off the sea air


You will of course need foot wear. You’ll need something to potter around the pool in that you can simply kick off in a second flat, something casual but more protective and something for the evening.

For pool time I’m taking flip flops. Now, I am not a fan, but they are functional. Please make sure yours are leather and not foam and rubber as they will get hot and sticky and plus they just look plain nasty.

Men's Leather Flip-Flops - Old Navy - Shoes - Men's Shoes
Old Navy leather flip flops $20.00

For the evening I will take 2 pairs of shoes, a classic brogue and a boat shoe, these can work with the long trousers or shorts (both without socks or with invisible socks as I will wear)

As a ‘go between’ for day or evening I will take a white pump like a low rise Converse. Again great with shorts during the day or more dressed up for the evening.

A classic brown leather brogue by Grenson £195.00
River Island Boat Shoes £45.00 
Marks and Spencer white pump £25.00

A great vacation look


I will not be seen dead in a baseball cap outside of my running (and that is only to keep the sun and the rain out of my eyes) Go for a straw hat, these are freely available and come in a range of styles and colours. 

New Look £9.00

New Look £9.00

BooHoo Man £10.00


Of course you will need sunglasses! I’m going for a classic Tortoiseshell and also a dark grey pair of the same shape. I will also take some mirror aviators simply because they are cool!

These three will mix and match with your different outfits and offer a cohesive look to the various elements that you put together. Plus if someone steals a pair while you’re in the pool sipping your Tequila Sunrise you’ll have another 2 pairs to wear!

Mirror Aviators by Storm at Debenhams £35.00

ASOS Wayfarer Sunglasses £20.00
Next Tortoiseshell effect wayfarer sunglasses £14.00

You’ll also need a bag. Something to keep your iPhone and iPod in while you’re swimming or getting drinks from the bar and to carry your beach towel, money, sun cream and that Dan Brown novel.  Its a good idea to choose something with long handles so that they can be tied to your sun bed so you can throw all of your valuables in it and keep them safe. A thief isn’t going to risk being caught trying to untie your bag when other people stupidly leave their valuables laying on their sunbeds!

Vintage tan sailcloth dufflebag – Not On The Highstreet £60.00

Fabric Tote – Cafe Press £10.00

Gant Canvass Tote £150.00

I’m also going to take a light scarf and my Daniel Wellington watch. The watch comes with a nato band that can be changed to match any outfit and the scarf will simply be to add a touch of elegance and dapper to an otherwise plain look and also to keep off any cool night breezes.

Linen scarves – Not On The Highstreet £35.00

Daniel Wellington 


Here are a few looks that I’ve put together based on what I’ll be wearing on my two weeks in the sun!

A casual beach or pool look

For pool or beach sun bathing

A trip into town

An evening at the bar

A day trip

From day to evening

A romantic beach side meal

A look to take you from day to evening

Beach combing

A smarter evening look

So whatever you decide to pack in your case make sure its dapper, avoid loud prints, avoid denim, avoid baseball caps and whatever you do, don’t drink pints and pints of free beer and make a total arse of yourself while turning bright red in the sun as you’ve fallen asleep in your intoxicated state. 

If you want to show your fellow holiday makers that you are a classy gentleman, sip a Gin & Tonic and make sure you thank and tip the waiter while tipping your hat. And please post a picture to Instagram and #thatdapperchap



Leave a Reply

Your email address will not be published. Required fields are marked *