Packing for a City Break

Booking a nice cheap flight for a weekend away is great. But paying extra to take a case with you is not. Nobody likes taking out the tape measure to see if your carry-on bag is within limits, or ‘the cram’ job followed by the messy unpack at the security scanners. 

Here we're going to look at how we can get the most out of your bag with putting the least in. And how to avoid all of the stressful moments, from closing the zip to getting through security without making a mess.

Having a great look and everything you need when you reach your destination means packing the right things, and packing them in the right way.

Nobody wants to pay extra for hold luggage... 

Get great looks and great outfits into your carry on bag, avoiding the extra charge.

It doesn’t involve taking a lot of things, but good folding and packing technique can give you that little extra room and keep wrinkling to a minimum. 

You don’t need a big or a heavy bag to get what you want...

Here's the deal:

Let's say you've got a long weekend booked, so that's 3 nights and 4 days. Of which you'll be travelling on 2 of those days at some point.

Obviously the time of year and the destination will affect what you're going to take. But the principles are exactly the same for both.

Actually realising that helps to avoid the situation when you're kneeling over your case looking around your room thinking 'what else will I need?'


What should you take?

Let’s start with the bag... 

The two best to choose from are the tote bag and the small carry on suitcase. 

Tote Bag

A tote bag is a staple for your collection, they are a holdall [with no dividers that take up valuable room], they have a large zip opening so you can get all your items in, and they look good. 

Unless of course you decide to use the single strap over the shoulder in which case it looks naff and they bang against your leg. 

But we’re wise to that and carry it as we’re supposed to: with the handles. 

If not a tote bag then a small carry on suitcase is the one. 

The benefit of these is mainly that they are rigid and offer more protection to your belongings, plus you can wheel it around. Function and fashion. Easy. These are primarily better for taking a suit. What you lose in style you gain in function with these, which is why they’re not to first go to.

No compromise here...

Toiletries. This is an area that you won’t really compromise on. So simply put, take what you need. You’re not going all that way to not look and feel your best. 

You want to look sharp 

Don’t feel guilty about packing for all your grooming needs. 

Tip: Where necessary, to negotiate the airline restrictions, you can buy yourself small 100ml containers and decant some of your product into it, but if you’re a frequent city hopper then it might be worth buying yourself a travel size version of your products. 

Keep in mind you can always avail yourself of a treat from duty free. 

Smells good...

When choosing your cologne, choose something that will work for both daytime and evening, your ‘go to’ scent will do nicely here. 

Tip: You may already be aware that as the cabin pressure changes your aftershave will vapourise, which means you’ll lose some to the inside of your bag. So it is better to minimise those effects by taking only one bottle. 

If you are torn between one with a lid and one without, go with the lid. The lid should help minimise the losses. 

Started from the bottom...

Shoes. By far the heaviest and bulkiest things to go into the bag, which is why they don’t go into your bag, they go on your feet. You’ll wear them not pack them. 

You will only need one pair of shoes. You may think that a pair for ‘this’ or a pair for ‘that’, but it can be almost guaranteed that you will not regret taking only one pair. 

If you want to take 2 pairs, make sure you're wearing the heavier ones.


So which pair? 

Winter kicks

Brown leather brogue boots. They will offer you support and comfort while walking around the city, seeing the sites and will also look great with any outfit, both formal and casual. They’ll go with your suit and they’ll go with your jeans. 

If you don’t like boots then go for the brown leather shoes. The tone of brown is completely your preference. Brown is versatile and good at covering up the inevitable scuffs and marks you’ll pick up along the way. 

Or for a casual look, go for a white trainer, which will look sharp and go with almost anything. Just make sure they’re clean!

Summer slips

For the summer opt for a driving shoe, boat shoe or just a plain old loafer. The leather will allow your feet to breathe, good ones will give you good support and comfort and they’ll go well with everything. 

Again, your white trainers will do well here as they can be dressed up with a cropped trouser, or they get be worn with jeans no problem. 

On the plane 

Keep comfort in mind -  feel good and look good at 30,000ft

It’s important to maintain good circulation as well as the ability to actually fold yourself into a comfortable position on the plane; being restricted is never nice. 

On you legs...

What you’ll want to put with your boots is a nice pair of dark slacks or chinos. With your loafers you can go for shorts or show a bit of ankle in your trousers.


A looser fit allows that comfort and give a more casual look, and this trouser type will have a little more give than denim whilst looking a bit sharper. 

On top...

A chambray or oxford shirt 

These more casual weaves are a bit lighter than the more formal weaves so you’ll stay a little cooler, they also look good with the sleeves rolled up. 

Tip: The coarser weaves will wear the inevitable wrinkles and travel better than any others. 

If you’re taking a jumper/cardigan, take a knitted one, they go well with everything. 

You can have it on under your jacket or under your coat or even on its own. 

Tip: Chunky knits do it best and they make a great pillow on the plane. 

Tip: If you’re taking a coat/jacket, then it can go in the overhead slung over your bag, you’re allowed to take a coat on board so save the space in the bag and have it over you bag between the straps. 

It’s worth keeping in mind that the free upgrades are likely to go to those looking the sharpest.

So what actually goes in the bag? 

Your underpants and your socks to name the obvious. 

Be sure to pack your dress socks as they’ll go with any look - if you want additional support for walking around and exploring hiking socks are recommended - just make sure they’re not white. 

Pack your jacket/blazer as this will take the least room between it and your knitwear. 

Your jacket is a must for the evening scene, it’ll look great with your knit or your shirt and when you find yourself in a restaurant or bar it won’t make you too hot and it will be nice to have on your walk to and from your hotel. 

Shirts Shirts Shirts 

Stick with the chambray and oxford weaves 

White or blue are the most versatile, you cannot go wrong with these, but go with your preference. Denim is also a good shout. 

They’ll  go well with all looks, they can be dressed up and dressed down so you can actually have the same shirt for two different events. Clever packing. 

Tip: These weaves also travel well, and by that we mean that they won’t hold a crease as much as a softer weave, but if it does it actually won’t affect the overall look. The rugged nature of the coarser weaves means that they actually pull off a few creases well, much better than twill for example. 

Tip: Their coarseness has other benefits as well, after wearing they won’t lose their shape and rigidity as much as the softer weaves, especially around the collar. 

Tip: They are also less spongy in nature so they’ll absorb less sweat which means you can get a bonus wear out of it; just make sure you air it out for a few hours after wearing it and hang it in the bathroom for a nice steaming. Fabric fresheners will come in very handy here.

Always have a spare...

Pack another pair of trousers, whether they’re jeans or something more on the formal side is really up to you, and depends on what you’ll be doing on your trip. 

Jeans are rugged and versatile and go with everything, but they can be a little taxing on long days of exploring and walking around. Chinos or trousers will offer you a little more comfort but are more susceptible to creasing and won’t hide any blemishes as well as jeans. 

It’s probably best to take one of each. 

Tip: Black jeans are great for both daytime and the evening, they also look better with shirts. 

When it comes to shorts take a light pair and a dark pair. That way you’ve covered all outfit bases. Don’t be tempted to pack twice as many shorts just because they take half the room.

Looking at what’s been packed, you have all the pieces to construct some great outfits. They are all interchangeable pieces so no matter what’s happening when you’re away, you’ll have a great look for it.

But that’s just half the story...

Getting it all in

Nobody wants to pay extra for hold luggage. We’ve picked our clothes wisely but good folding and packing technique can give you that little extra room as well as keep wrinkling to a minimum. So it’s worth getting right.

From the bottom... 

Pack from most creased to least creased. 

Start with putting your underpants on the bottom, fold them in half once, and stack them with the waistband at alternative sides to create the most even pile possible. 

For your socks you want to lie them flat on top of one another again creating nice neat pile, you’re probably noticing a pattern here...nice neat piles. 

Your trousers, folded in half and folded twice on the leg, so that they’re as square as possible. 

Fold Fold Fold

Then your shirts, you want to fold them just like they do in the shop. 

Tip: Not only will this help with space saving but it will provide enough structure so they don’t get scrunched in your bag. 

If you’re taking a jumper then fold it the same way, if it’s a cardigan then do up the buttons and….fold it the same way. 

Pile ‘em high

Pile up all of your clothes on top of each other, keeping it as square and even as possible. 

The order is: underpants, socks, knit, trousers and shirts.  

Tip: Get yourself a length of ribbon and wrap it around your clothes pile like a parcel. Ribbon won’t dig into your clothes adding creases because it’s flat, and wrapping it up will keep the pile sturdy and prevent it moving around in your bag. 

That’s the clothes done

Onto the Wash Bag

The rules for the carry on liquids is anything like gels, foams, creams, oils, sprays...basically anything that isn’t a solid needs to go in a see-through plastic bag roughly 20cmx20cm. But you already knew that.

It must not contain any more than 1L worth of fluids. So your deodorant, shower gel, shampoo, conditioner, shaving cream, hair pomade, moisturiser, beard oil, toothpaste, mouthwash and after shave can all go in without a problem. 

Tip: Pack all the fluids into the plastic bag and then put the plastic bag into your wash bag, just so everything is together. Also if anything leaks - your wash bag will save your shirts. 

Tip: Your hair brush, tooth brush, razor, floss and anything else can go straight into your wash bag. 

Tote bag...Assemble!

Now that we have everything together, all we need to do is assemble to bag. 

You’ve two sides to your bag: soft and hard. 

Put your lighter shoes (if you’re taking them) to the one side, grab your clothes parcel and put that in the other. 

Your wash bag will go on top of your shoes and...well...that’s it. 

You’re packed. 

There should be plenty of room for your laptop or iPad in there, as well as your books and anything else you might be taking. 

Now at security you can easily access your electronics and wash kit and then re-assemble the whole thing no problem! 

Tip: If you want to take a briefcase, camera bag or something like that then you’re fine to do so. Most airlines say you’re allowed one piece of hand luggage and one personal item. 

So with all that, you’re on your way! 

Happy packing and safe travels!