How to Travel with ONE Bag & ZERO Sacrifices – Packing Hacks

Due to all the varied and intricate parts of our wardrobe, packing is challenging enough, and it can be hard to pick the right pieces, which leads to overpacking. Oftentimes, we menswear enthusiasts pack extra items just in case, that never end up being used. So, how can you pack light and still look good, and do it all in accordance with TSA’s recommendations? We’ve got tips here!

Why Travel With Only One Bag?

At this point, you’re probably asking the same question. If you’re used to traveling with several different pieces of luggage, you might be wondering, why should you only travel with one bag? Well, there are serious benefits to taking all your luggage and containing it and just one suitcase.

The first is that most airlines make you pay for a large check bag, but you’re typically allowed to take a carry-on piece of luggage, as well as a personal bag. So, not only will you save money, but you’ll also be able to keep everything together and keep the airline from losing your luggage. This can also add to the enjoyment of your travels, as you have fewer things to remember and keep a hold of.

Something that many travelers complain about is the price of snacks and beverages while traveling, which leads many people to stuff their bags full of food, but your bags really should be for your clothing items, and not for your mid-trip buffet. Plus, there are always options to get food or drinks on the flight anyway.

Traveling light makes you a lot more mobile on your trip, allowing you to do various things without having a bunch of cumbersome luggage. It will certainly be easier pulling one suitcase across the cobblestone streets of Italy, than five. The real key to success when it comes to traveling light is to make your travel outfit count.

What to Wear When Travelling

Wear Real Clothes To Travel

It should come as no surprise that we are firmly against wearing athletic wear at the airport, but you kind of got that from the channel name, right? Therefore, you really want to make sure that you’re wearing excellent clothes to wear on the flight, in addition to what you carry in your bag.

Wear a Versatile Suit

When it comes to our recommendations, we would recommend starting with a really great suit. As a general note here, all of the suggestions here can relate to any weight of clothing, depending on the season or the weather that you’re traveling to, and if you’re stuck for any ideas, take a look at our guide on seasonal style.

Start off by choosing a versatile suit; gray and navy are going to be your best options, as they look great for business attire, as well as something to wear by the bar at cocktail hour. But if you’re looking for something more interesting, pick a classic Prince of Wales check suit, as it’s a little bit more unique than what most people will see. If you choose one in a classic menswear color, the pattern will match a wide variety of things that you’re going to be able to wear.

A well-fitting suit is an excellent choice of something to travel in, as Raphael often does. He often mentions that he gets treated a lot better when he dresses up at the airport, and if you’re worried about that suit jacket while you’re in your airplane seat, thinking, “Man, that’s going to be really uncomfortable,” you can give it to a stewardess, and they will put it away for you upfront with other jackets.

One thing to note here is to take a suit with a material that can be broken apart into a jacket or trouser separates. I wouldn’t recommend taking a shiny, very fine business suit. I’d recommend a flannel, open-weave wool, or fresco – something that you can use for the jacket and the trousers separately.

My personal favorite is taking a navy blue plain weave because you can wear a navy blue jacket as a blue jacket or blue trousers as blue trousers.

Wear Formal Shoes

We also recommend that you wear your formal shoes. They’re often bulkier to pack and, therefore, you should wear them, and you’ll free up more room in your luggage. Picking a pair of black oxfords is the obvious choice, but if black isn’t your thing, you can substitute these for dark brown or a burgundy or Oxblood color and, if you don’t like the idea of having to unlace your shoes or you don’t have TSA pre-check, wear a pair of nice loafers.

Whatever style you choose, make sure to take a travel shoehorn with you so you don’t damage them by putting them on and taking them off.

Wear Classic Accessories

Also, add classic accessories. No matter where you go, wearing things like a classic wristwatch or a white pocket square is always a great touch to your outfit.

We also recommend that you pack, not wear your cufflinks. As you might imagine, metal cufflinks and the security machines at an airport don’t really mix well. The same can be said for metal collar stays.

We would recommend you take these out of your shirt and put them in your bag, so choosing a shirt like an Oxford cloth button-down is a great choice as the color’s soft, it’s comfortable, and you don’t have to worry about the color not being starched and pressed sharply.

We also recommend that you wear, not pack, your overcoat. So, whether it’s a heavy overcoat or a light trench, this is something that’ll take up a lot of room in your bag, so we recommend you wear it and, if you’re worried that you’re going to get too hot, you can always take it off and give it to a stewardess. But, if you get too cold, you can use it as a blanket on the airplane. 

Packing for a Short Trip

Now that we’ve built your perfect travel outfit, let’s put it all together and put some of this in a suitcase. So, in this section, we’ll be looking at packing a bag that is carry-on size or smaller, and while we’re looking at a carry-on bag if your trip is even shorter, maybe a 24-hour trip, just adjust your bag and your items accordingly.

Pack an Odd Jacket and Trousers

We also recommend packing a jacket and trousers. You want to choose a jacket that will work with the other trousers, the trousers from your suit as well as these, and a jacket that will work with your suit trousers as well as the trousers that you bring with it.

A jacket in browns and greens is a great color choice here as it will go with the blue from your suit or, if you choose a gray suit, it’ll go with those as well, as well as the brown or cream of the trousers. So, with that being said, it’s very hard to go wrong with picking a classic pair of khaki chinos.

Fold the jacket using the inside-out-shoulder method and wrap the trousers around it to reduce the number of fold lines and creases in them. Packing this way will protect both garments individually, and it means you don’t have to worry about bringing bulkier heavy clothing hangers with you.

So, at this point, you have one great versatile suit, one jacket, and one pair of trousers. This gives you six combinations.

Pack a Spare Pair of Shoes

Some contrast to what you’re currently wearing, so if you have a pair of smart oxfords, maybe pick a suede loafer. Use your socks and underwear as makeshift shoe trees and shove them inside of your shoes, and, if you wear belts, pack a belt that will match these shoes as well.

You can even roll up the belt and put it inside the collar of your shirt to help the shirt collar keep its shape, and if you wear suspenders, you don’t have to worry about packing multiple pairs that match, as you’re less likely to see them because you’ll have your jacket over them.

Pack a Fresh Shirt for Each Day of the Trip

The shirts will give you more of an opportunity to create more unique combinations than packing more suits and more jackets. While it might be tempting to do a Don Draper and pack your bag full of white shirts, don’t be afraid to add a little bit more variety. After all, variety is the spice of life, and, if you stick with subtle patterns or simple colors, outfit creation will be a breeze.

This shirt packing tip is also the case for longer trips as it’s good to have a fresh shirt for every day and ensure you fold your shirts neatly so you reduce the chance of having to iron them when arrive.

Pack a Merino Wool Sweater or Cardigan

Merino wool travels well as it’s naturally elastic and it doesn’t wrinkle easily. It’s also lightweight but warm, which is a great option choose a V-neck style or a cardigan style, as you can use it with a bunch of different options, and you can wear it under your jacket. Also, make sure to choose it in a solid color – no crazy stripes or checks. You want to have something that you can wear with a lot of different outfits.

Pack Two Ties, Two Pocket Squares

Although accessories can be small items, they really add up. I mean, look at how many Raphael has. So, if you limit yourself to a few ties and pocket squares, you will have what you really need, and, if you pick ones that are versatile, they’ll go with all the outfits and combinations that you can put together.

Focus on more robust types like knit ties or wool pocket squares, as these travel and wear well. And while you’re looking at accessories, if you’re someone who likes to wear French cuff shirts, throw a pair of French cuffs in your bag, and if you choose a classic design like a monkey’s fist knot, it’ll go well with every occasion.

Packing For a Longer Trip

For longer trips, you’re going to want a larger case. So, we’re going to now focus on packing a bag up to and including check-in size. As the saying goes, often the simplest solution is best, so transfer all of your items from your carry-on over to your check bag. So, these next items are going to build upon the previous list we’ve already established.

Add an Extra Suit

Here, you can add an extra suit. This suit should still be versatile, so if you brought a navy, maybe bring your gray and vice versa. I would still recommend packing a suit that makes sense to where you’re going, so if you’re going to Miami, don’t pack flannel in the middle of July.

Also, try to pick a material that can be broken apart, such as a high twist wool. Don’t choose a shiny business suit unless you have a very formal event to go to. Also, keep in mind that you have the opportunity here to bring in different details, like a double-breasted suit.

So, if you keep things versatile and interchangeable, now you have nine different combinations. 

Add a Waistcoat

Packing a waistcoat in a neutral color is also a great choice, and, if it works with all the other parts of your wardrobe, now you have 18 combinations.

Add an Extra Pair of Shoes

We also recommend adding another pair of shoes; really any shoe from our list of essential shoes will be a great choice here. This is also an opportunity to bring in more details like broguing or a monk strap. And unless you need to really economize on space or weight, adding a pair of travel shoe trees are good here, then you’ll have one pair that you can rotate through all the shoes you brought.

Add a Couple of Extra Accessories

It’s a good choice here to add maybe another tie or a few more pocket squares or even a boutonniere. You also could consider other options, such as an ascot, to add a little bit of variety to all of your outfits.

Perfect Packing Pointers

So, with all your packing lists now sorted. Let’s turn our attention to some expert-level packing tips. This way, you have the most enjoyable and stylish time on your trip.

1. Aim for Versatility

An extra pair of shoelaces are the best few dollars that you’ll ever spend. I mean, after all, you never know you could be halfway around the world with a nice pair of shoelaces and your shoes break. If you keep an extra spare set, they’re virtually weightless and take up no space and it’s good to have in case of a style emergency.

2. Reduce the Size of Things Wherever Possible

Also, reduce the size of things wherever possible, even if you have a lovely, beautiful umbrella, taking a full-size one that takes up the entire width of your suitcase is not a great choice. Choose a telescoping umbrella instead or a small travel-size one.

3. Include a Spare “Emergency” Bag

Also, if you can, pack an emergency bag. No, we’re not talking about a medical kit here. It’s nice to have another small bag, such as a mesh one or maybe a small canvas tote, that you can bring things home in if you end up buying more on your trip.

4. Allow for Wild Weather Changes

Also, allow for weather changes. Even in the 21st century, weather forecasts aren’t 100% accurate. So if you want to bring a pair of rubber galoshes, it’s a great choice.

5. Take Minimal Toiletries

Here’s another packing key, take minimal toiletries. Oftentimes, toiletries are provided at many hotels, and you don’t have to bring a full bottle of shampoo. There will often be options for you. This is also a great opportunity to use small fragrance samples rather than taking the entire bottle.

6. Make Sure Your Traveling Clothes Fit Into Your Case

Also, make sure that you can fit your traveling or airport outfit into your suitcase as well. You don’t want to pack your suitcase completely full and then, on your way back, want to ditch the overcoat and put the overcoat in your bag, and it doesn’t fit.

7. Consider “Packing Cubes”

Finally, you should consider things like packing cubes. They can be very useful in keeping different elements of your suitcase separate, and there are versions where you can vacuum seal them, so you get more room available to you in your case.

Conclusion

So, when it’s all said and done packing, light and looking good certainly can go together hand in hand. And hopefully, we’ve shown that it’s very achievable.

By the way, don’t feel like you have to stick to the one-bag rule. If you’re going to go on a two or three-week vacation, don’t be like me when Raphael and I went to Europe last summer. It’s certainly worth paying a little bit extra to have more clothes at your disposal.

This guide was inspired a little bit by Raphael and my travels to Europe last summer. We visited Jack across the pond and went to Italy and Portugal to visit some of our makers, and as we went to baggage claim in Manchester Airport, Raphael picked up his bag and he asked, “Well, where’s yours?” and I said, “I have it.” It was just my carry-on, as well as my computer bag. Raphael was pretty shocked that I could pack basically two weeks of clothes for a trip to Europe into one small carry-on bag, but I’m also a notoriously light packer.

I wore one blue sports jacket with a pair of chinos. I packed an extra sports jacket with two other pairs of odd trousers, and packed four shirts. I also packed two pairs of unlined loafers as they’re easy to compress and fit into the shoe compartment of my bag. They’re also very easy to get through the airport in if you have to take them off.

Technically, I broke our shirt rule. We were gone for 14 days, and I took five shirts, but I also knew that we would have laundry at our disposal. So, it also helps to know where you’re going and where you’re going to stay. But, hey, you don’t have to be like me. You can certainly bring more clothes and more variety. This is just a little personal anecdote.

Which one of our packing tips will you use on your next trip? Let us know in the comments!

Outfit Rundown

Today, I’m wearing an outfit that you would find me in on our trip to Europe this coming summer. I really just need to add a sports jacket, and I’m really good to go for a variety of different occasions.

I’m wearing a denim shirt, which is a nice casual option. It bridges the gap between very dressed-up like a starch white shirt and a more casual polo shirt. It can dress down a suit or a more formal sports jacket, as well as dress up a more casual outfit.

I’m wearing a pair of cream cotton trousers. These are very comfortable for the airport and for travel. These are made-to-measure by Collaro in Singapore.

On my feet, I’m wearing a pair of comfortable loafers with a rubber sole. These are in the Summer Walk style that has been made famous by Loro Piana. These are by Skolyx and Yonko, and they look great with different shades of brown.

For my cologne today, I am choosing the Roberto Ugolini Rosso. It has really nice, airy with a little bit of spice – great for the summer months. If you want to check out this fragrance or any of the other fragrances or pick up some accessories for your next trip, check out the Fort Belvedere shop.