First of all, it starts with a choice of the right suitcase or carry-on. Personally, I’m a big fan of wheels, especially four wheels, because you can easily maneuver them with one hand.
So when you start packing, I suggest to first lay everything out on your bed or maybe on a carpet, in a clean space where you have a good overview. Depending on the length of your business trip, you may just need one pair or sometimes two pairs of shoes. I suggest you wear a pair when you travel and keep another one in your suitcase because shoes last you a lot longer if you don’t wear them consecutively day after day. To save on space, you can put your underwear, as well as your socks, rolled up and stuff them in your shoes, that works like a substitute shoe tree without having the extra weight. Because shoes are dirty and everything is close together, I suggest putting your shoes in shoe bags.
Essential Items To Pack
Black Dress Shoes
Black is the ultimate color. I suggest you go with a black cap toe oxford. Alternatively, you can also go with a black oxford half brogue or black oxford quarter brogue. A little bit of broguing makes it a little less formal, at the same time, it’s perfectly appropriate for everything, from boardroom meetings to general office meetings. If you have a big foot and you have issues with the closed lacing system on an oxford, a derby shoe is acceptable as well.
Oxblood Dress Shoes
The second pair to bring is a dark red or oxblood burgundy colored dress shoe. It could either be a tassel loafer and you could travel with that because it’s easy to take on and off when you’re through security or you could go with a derby shoe or maybe even an oxford. I like the color burgundy because it’s dark enough to be appropriate for most office and business environments, yet at the same time, you can wear it interchangeably with any kind of brown tone if you go to a more casual outing afterwards or during the business trip.
So if I had to bring just one pair of shoes on my trip and I knew there were events with different degrees of formality, I would opt for an oxblood or dark red shoe. Maybe during the winter, you can get away with a pair of boots. If your space constraints in your carry-on, I suggest putting one shoe on one side and one on the other. Ideally by the wheels, that way, the weight of the shoe won’t squish your suits or your shirts or any other garment on your carry-on.
Even if you’re just going on a one day trip, there’s always a chance that someone will spill something on you and it’s much better to have something that you can change into than having to figure out where you can have it dry-cleaned. Honestly, I think plain white solid shirts, maybe cream, or light blue are perfect. You can also go with pastel tones such as light yellow, light green, light lavender, and so forth. Now, a proper business shirt usually doesn’t have a chest pocket because you shouldn’t use it anyways and you also want double cuffs or French cuffs for cufflinks. Now, if you travel to a climate that is warmer or maybe if you don’t like cufflinks, you can also get away with barrel cuffs. It’s acceptable in this day and age.
If you decide an undershirt is right for you, I suggest not to go with the traditional fine rib wife-beater undershirts. Instead, I suggest you get t-shirt like undershirts that sit fitted on your body with relatively tight sleeves and a deep cut v-neck because that way, if you wear a dress shirt without a tie and you wear a dress shirt unbuttoned, people won’t be able to see the t-shirt underneath which is a style and fashion faux pas. In terms of color, I suggest you pick something that is as close to your skin tone as possible so don’t go with white, rather go with black or maybe heather gray or even skin tone colors if you can find them. No, a regular t-shirt is not a good substitute because it’s thicker than an undershirt and has thicker seams that you can see on the outside of the shirt.
Business Appropriate Suit
There’s probably no other garment that is more business appropriate than a dark suit. If you have to pick one, I suggest to go with a navy worsted suit, ideally single-breasted with notch lapels, either one button or two buttons, side vents, maybe some cuffs at the bottom of pants so they pull down the pants and prevent any potential wrinkles. In terms of weight, I’d go for a three-season weight. If you want just one all-rounder, you can also opt for something with an open weave. That way, you feel the breeze because sometimes when you’re in an office environment, it can get quite hot but you know yourself if you’re likely to overheat or if you feel cold all the time.
If you are in a colder climate, you can also go with a flannel suit. If you decide you want to bring a second suit, I suggest going with a double-breasted suit simply to mix it up and have different degrees of formality. Also, I wouldn’t go with the same color but have maybe one in gray and one in blue. If you decide to just bring one suit, I think the navy suit is ideal because you can wear just the jacket with a contrasting pair of pants, either let’s say gray flannels or a pair of chinos and it looks like a blazer combination, that way, you have a more versatile wardrobe and you don’t have to bring on an extra jacket.
When it comes to accessories, I think a necktie is essential especially in a classic business environment. If you’re a little more flamboyant or if you are maybe independent or in an area where dress codes are a little more relaxed, you can also go with a bow tie, otherwise, I suggest to stay with a classic necktie.
A pocket square can really help to make your outfit look more polished. So if you have a white shirt, a white linen pocket square especially in a TV fold or a crown fold, it can add a finishing touch.
I suggest going with a simple pair such as a monkey fist knot cufflink. Skip the colored enamel cufflinks as well as the gemstone or diamond cufflinks. They’re better for evening wear or areas or events where you know you can just be a little louder. If you want to travel light, I suggest putting the cufflinks right into the double cuffs of the shirt before you fold them. The same is true for your collar stays, put them in the shirt so you don’t have to pack them separately. If you have more items such as rings or watches, you probably want to go with a travel jewelry case. If you work in a classic white collar environment, you probably don’t want to wear a boutonniere. I, on the other hand, oftentimes wear one simply because I can and I enjoy it and the Green Fort Belvedere box is the perfect travel companion for that because it protects your flowers and that way, they stay in shape and you can wear them wherever you are on the globe.
I suggest keeping a small bag that you can easily remove at any point in time because sometimes at security, you have to remove it depending on your status. To save on space, definitely go with travel sized items and don’t bring your regular size aftershave, shaving cream or toothpaste. I know it’s just a little thing but all those items add up, they add weight, and especially volume and bulk. I also find that sample sizes of either cologne or shaving cream sometimes also shampoo are perfectly enough for a short business trip and they hardly take any space at all. So keep that in mind.
Rather than a safety razor or a straight razor which you can’t bring in carry-ons, I suggest you go with an electric shaver. Yes you may also go with a cartridge system, however, I find the shave to be inferior to an electric shaver. If you go with a wet shave and it’s my preferred item because I just bring one item with one charge and I can use it, I don’t have to worry about the blades getting dull or having the right blades or a TSA agent not knowing what he’s talking about and who made me throw away something I actually need afterwards.
Of course, you also need socks and underwear but that goes without saying. For a business trip, I suggest you go with over the calf socks because you will never want to expose your calves.
Sweater Or Cardigan
If you want a few more casual items, like a sweater or a cardigan, it’s okay to pack it. I suggest going with thinner cotton ones rather than bulkier wool ones because space is very limited in your carry-on. If it’s warmer, you also may want to bring polo shirts, if you want to work out maybe a pair of workout shorts and t-shirts. All of these shouldn’t be folded but rolled, unlike your dress shirts which should be folded.
Personally, as an online entrepreneur, I always bring my laptop as well as my camera gear in a separate leather bag that I can put on top of my carry-on that I can hook on so it doesn’t fall off and I can still easily push it with one hand while doing something on the phone or checking things out so it’s extremely convenient.
Overcoat For Winter
It could be a double or single-breasted overcoat in either navy or black or charcoal. If you travel during the warmer months of the year, I suggest you bring a trench coat. Yes you can also go with a traditional kind of khaki trench coat but it stains more easily then let’s say a black or navy one.