How to Travel in Style: The Ultimate Guide

How to Travel in Style: The Ultimate Guide

Moving through the world in style is an essential these days, especially as travel – for business and pleasure – ramps up again at a faster pace than ever. Bringing your wardrobe on the road, so to speak, needn’t be overly complicated or too much of a hassle. And you needn’t be weighed down by overpacking – versatility remains the name of the game for the modern gentleman. 

It comes down to knowing what to pack, yes, but also knowing how to pack your tried-and-true essentials, be it a favorite charcoal suit, a crisply cut light blue dress shirt or elegant leather dress shoes. And while it’s easy to load up a weekender bag with rugged, casually cool pieces for quick getaways – like wool jumpers, a henley, blue jeans – bringing tailored essentials on the road requires more finesse.

It also requires a proper carry-on bag and proper storage, plus accessories like a toiletries kit and a few other essentials (a sewing kit might be helpful for tailored repairs for instance) – more on all of this soon. 

When it comes to packing suits, dress shirts and dress shoes, the details – naturally – make the difference. Here’s what to know about packing for travel in style...

Knowing What to Pack (And A Few Suggestions)

It’s one thing to be able to closely examine your entire wardrobe at home, particularly in the realm of finely tailored clothing, but a more efficient approach will serve you well as you hit the road: Remember, the more versatile your packing list, the easier it’ll be to travel. And that certainly extends to more formal wear, particularly if you’re traveling for business or for a wedding or another, dressier affair. Start from the ground up, and consider where you’ll be going and what the itinerary involves.

The length of the trip also dictates what to pack, but consider the possibility of 3-4 outfits: A dressy outfit for the office, for formal nights and meetings (ideally a suit). Should things lean more casual, a blazer in a neutral color can function much the same way, and can even be paired with jeans or chinos as needed. Then, look to round things out with a look consisting of more casual-yet-versatile pieces (for example, a pullover sweater, a travel jacket and blue jeans or chinos). 

If the occasion is a work conference or work meetings, finely polished dress shoes in your preferred color – say, classic black or dark brown – are going to prove highly versatile. Dark brown leather dress shoes in particular can even work with dark blue jeans for slightly more business casual situations – just be sure you’re bringing a leather dress belt in a proper, matching leather color. 

Keep in mind that you needn’t bring multiples of every item: Rather than bringing three sweaters for a 4-day trip, for instance, consider packing one or two. That move will save space in your luggage – and we’ll get to what luggage will serve you best momentarily. With just that seemingly small list, you’ll create the possibility for multiple outfits, without needing to bring so many items. 

Bear in mind, that especially for business travel, some hotels might offer laundry or suit or shirt pressing services, and an ironing board in your room goes a long way towards keeping your clothes fresh – and extending the life of your garments, all the while without overpacking. 

Packing for Business Travel

The demands of your day naturally inform what’s going in your suitcase, so consider the nature of your work week – will a charcoal suit suffice? Is it appropriate to wear a suit sans tie? Should my suit lean more conservative and classic, or does the occasion call for a suit with some personality, like a subtle pinstripe design? 

Versatility is key across the rest of your wardrobe – a charcoal suit, for instance, wears well with black or dark brown shoes, matches up handsomely with light blue or white dress shirts (or virtually any other shade) and can work well with a wide variety of ties Note that navy suiting serves much the same purpose. 

A good rule of thumb might be packing two-to-three versatile dress shirts, based on the number of tailored engagements you’ll be involved in. A white Oxford shirt also works well for slightly more casual situations – for instance, it’s a shirt you can wear with a V-neck or pullover sweater, or even one of our Anatoly & Sons Traveler Jackets

The proper accessories are also crucial, but in order to streamline your packing list, consider the trusty white pocket square as your most vital finishing touch to a tailored suit. Additional accessories like cufflinks are vital for a French cuff shirt, and a tie bar in a proper width (based on the width of your tie) is a refined move that adds flair and personality. 

Keeping It Casual 

Not every portion of your trip might involve a tailored suit and ultra-formal affairs. This is where menswear wardrobe workhorses can come into play. When in doubt, opt for maximum versatility and consider more casual trousers you can style with most anything: In this case, the dark blue jean or the dark tan (British Khaki) chino are wise moves. They wear well with jumpers, with chore coats and Oxford shirts, or with a blue Oxford shirt and a bomber jacket. 

Of course, knitwear like the classic henley or a grey thermal long-sleeve shirt can function in that same way: Pair a henley or polo with a field jacket or beneath a quarter-zip shirt, or use a crisp navy T-shirt beneath a bomber jacket or sweater if things should prove even more casual. 

Sportswear classics like the navy polo are also a wise move in warmer climates. The same can be said for white leather sneakers, should your plans turn ultra-laidback. The rest of the time, your tried-and-true dress essentials will serve you well from head to toe. 

Perfect Preparation

Just as you might write down a grocery list or mentally plan a packing list, the way you prepare for travel is sometimes half the battle – having a solid visual idea of what you’re bringing and where you’re going makes things that much easier. 

Experts recommend laying out your clothes at once as you pack, using, say, a bed or another available surface, that way a clear view of your packing list is possible. That also gives you the chance to expertly fold your shirts, trousers, jeans and more. 

And it makes it easier to pack accessories nicely: For instance, a media case might be used to store phone chargers and other tech cords or headphones. Your toiletries kit holds your grooming essentials, and is much more elegant and stylish than, say, a clear plastic bag. 

And a few other tips go a long way: You might pack your leather dress shoes with a travel shoe tree, so they retain their shape, or pack your socks and underwear in those same shoes as an alternative. Zip compartments in your luggage and carry-on can also be used to hold socks and underwear. 

If you’re trying to travel in streamlined fashion – say, with one carry-on bag and one small briefcase for your laptop and work documents – efficiency comes in very handy, so ensure your travel gear is packed accordingly. 

How to Pack a Jacket (And Other Essentials) for Travel 

Be it a business conference, client meetings or other formal affairs, a suit and stylish dress shirts and accessories are nothing if not packed properly. How to pack a suit for travel is a critical move, and it also comes down to the vessel in which it’s being carried.

In some instances, you might opt to wear your suit or blazer onto the plane or a train – this certainly lightens your luggage, and note that a stewardess can put your jacket away for you up front on the airplane. That same jacket can also be pressed by a professional at your destination. 

So, how to best pack a carry-on for travel? Your dress shoes, like other heavy and bulky items, should be packed on the side of your suitcase. But the most crucial part of packing tailoring for travel? Packing your blazer or suit jacket in the best manner possible. 

1. Start by turning the jacket inside out with one shoulder, then using the facing (opposite) shoulder to push through the first shoulder. From there, line up the lapels and collar, folding it in half before laying the jacket length-wise inside the bottom of your suitcase.

This folding method ensures the exterior of the jacket avoids damage. Experts also recommend folding your trousers within the jacket itself – start by matching your trousers length-wise from waist to cuff, then place the trousers flat within the suitcase, atop the jacket. 

2. Half your trousers should rest inside the suitcase, atop the jacket, and half outside. Here’s an even more handy travel hack: Your crisply folded dress shirts are then placed atop both the trousers and jacket, with your shoes resting on the side of your carry-on suitcase. Much the same can be done with any more casual knitwear pieces you might be packing. 

3. Other cold-weather accessories – a sweater, a scarf or gloves – can be added as needed to your carry-on, based on where you might be traveling. Ties can sometimes be rolled, as you might find in a shop display, or folded in half and placed length-wise on top of other items (within the "suit and trousers" combination).

4. To round out your carry-on, simply fold your trousers over the top, using a soft crease at the knee, followed by folding the top half of the jacket over the entire combination. 

The end result is a streamlined, effective way to pack a carry-on suitcase for travel – should your trip call for a blazer and chinos rather than a suit, for instance, much the same method can be followed. 

Luggage: The Right Tools for the Job 

It’s like we noted earlier: A weekender bag can suffice for ultra-casual trips to more rugged locales (say, a winter cabin getaway), but business travel calls for both efficiency and proper support and space for your tailored essentials. 

Experts recommend a sturdy suitcase with “spin” wheels and an easily adjustable handle – your carry-on briefcase is then often equipped with its own handles or straps to attach to the carry-on suitcase itself. 

Other materials, like abrasion-resistant canvas with leather accents, are also ideal options for a carry-on suitcase, and much the same can be said for your leather, canvas or canvas-blend briefcase. When traveling for business, look to more polished accessories – while you might pack a durable waxed cotton backpack or brief from a heritage outfitter for a weekend getaway, look to more elegant options like sleek leather or a simple black briefcase

Brands like TUMI specialize in carry-on suitcases specifically made for business travel, as do companies like Zero Halliburon and Rimowa. Options abound at every price point, but all should be TSA-approved and easy to pack for three-to-five day business trips. 

Dressing with Comfort and Style in Mind at the Airport 

Personal preference and comfort are certainly crucial when trekking cross-country or across the globe, but at Anatoly & Sons, we feel it’s still possible to retain a sense of polished style while heading to your destination. Aside from what’s in your carry-on suitcase – and setting aside the fact that you might end up wearing a blazer onto the plane, for instance – there are ways to retain elegance and style without sacrificing a proper fit. 

An unstructured jacket, especially in a cotton or cotton-linen blend, or a breathable wool blend, forgoes the padding and structure of some suit jackets and blazers, all the while delivering polish and versatility. Or if you're looking for something more casual, pieces like our Anatoly & Sons Trailblazer Traveler Jacket are breathable and lightweight, with enough refinement to work in most any situation. 

Other prized materials, like lightweight, cotton / linen dress shirts or even a knit polo or a T-shirt made from a premium material, are a wise move as another base layer. Opt for neutral, crisp colors like navy, khaki, olive or light grey for maximum versatility in the air and on the ground. 

Provided you’re dressing slightly more casually, chukka boots or dark leather sneakers might prove a stylish but versatile, comfortable footwear choice. But again, if you’re opting to wear a jacket on the plane (which a stewardess will then store for you), then a business casual travel outfit (say, centered around tan chinos, a white Oxford shirt and dark brown leather dress shoes) is likely advisable, as opposed to sneakers and denim. 

Remember, your travel look is effectively part of what you’re packing and bringing on the trip itself – versatility is crucial. 

Packing for Cold Vs. Warm Climates

The great news when packing for business travel is that, with a few key tweaks, many of the same pieces can function very effectively. Materials like cotton chino and suits made from tropical wool are worthy of warm weather, while flannel suits and wool jumpers can be worn in colder climates. Charcoal and navy suiting, white and light blue dress shirts and finely crafted leather dress shoes work quite well – leather dress boots might suffice for an especially wintry destination, however.

travel accessories

The key difference lies in your accessories – your scarf, beanie, or flat cap and gloves require more space in your bag for frigid conditions. And you might opt for more lightweight materials, like cotton or linen blends, in your tailoring and trousers based on the weather. And knitwear, like a navy polo, might function as a reliable substitute with a khaki cotton suit, for instance, in a very warm climate. 

The Final Word

Packing for business travel, especially packing suits and tailoring, becomes easier and more efficient each time one steps up to the suitcase and starts the process. Efficiency also makes the process easier, be it using three or four dress shirts, relying on the same charcoal suit and leather dress shoes, or mixing and matching combinations with an unstructured jacket or a jumper. 

Taking the crucial step of turning your suit jacket inside out, packing around it accordingly with shirts and accessories, and using your dress shoes as storage space are all critical moves, too. And be it packing for cold weather or warm weather, many of those same pieces – including suiting and dress shirts – can still prove highly versatile. Traveling in style, with refinement in mind, is certainly possible, so plot your next trip accordingly. 

Recent Posts

View all
Are Suspenders Old Fashioned?
In Praise of the Preppy Look
Raw Origins: The Legacy of Levi's Denim