How we dress when we travel is either a pointless consideration of the vain and frivolous among us, or it’s an important visual message that often conveys much more than we had planned. Discerning travelers know the answer: it is a significant factor in how travelers are perceived abroad. It is also, however – and perhaps even more important in some venues – a powerful influence on how travelers behave.
The web is full of articles on how to dress for a long flight, things you should never wear when traveling abroad (usually these are directed toward Americans), do’s and don’t’s of travel dressing, and what seems to be the most searched for type of travel dress piece: how to dress for a cruise. We would suggest that when people search for articles on how to dress for travel in general and cruises in particular, they want to know how to feel comfortable – both physically and psychologically. People who search for these answers care – as do we.
Throughout our years of travel via plane, train, car, ship, and on foot, we have observed that dressing is important in the following travel situations:
During airline travel: First, you need to be comfortable, but that doesn’t mean that you need to look like you just crawled out of bed with a hangover. Looking like you care often has the same effect on other people: they might just care about you should you run into difficulty. You can proclaim the superficiality of taking care when you travel, but there is ample evidence to support the contention that looking your best often helps to be treated well – like it or lump it. There is another important dressing guideline for air travel: dressing for the inevitable security check. We were once rushing through security to make a connection between Canada and the US onward and found ourselves in the security line behind a parent and teen-aged son. Said teen-aged son had clearly not received the memo about what a security screen would entail. He had layers upon layers of clothes that all had to be removed one at a time after going through the metal detector and back out of the metal detector. He had several chains around his neck, a chain holding his wallet to his trousers, and on and on. Not a pretty sight in any event, and we were purple with fury.
Touring cities: When we tour cities, we walk. That means footwear is our prime consideration, but it is not the only one. We prefer that our attire not scream “tourist”; this means that our footwear does not under any circumstances consist of white sneakers. Given the plethora of really lovely choices of walking shoes these days, it is puzzling to us how many people continue to wear these monstrosities. If you can afford to travel, you can afford a good-looking pair of walking shoes. As for clothing, it ought to be dictated by the weather and local customs. If you’re visiting Istanbul, for example, regardless of how hot it is, if you want to visit a mosque, you’re going to have to be respectful and dress the part. Check with the local tourist authorities for specifics so that you aren’t surprised by the posted signage. Women visiting conservative cities should always have a scarf in a handbag or around a neck for use as a head and shoulder cover.
On a cruise: When cruising, clothing needs to be dictated by itinerary
(for example, people on South Pacific cruises dress differently than on Mediterranean cruises), weather and your choice of cruise line (Carnival cruises has a decidedly different expectation of how one will dress than does Seabourn, for example) – they all have differing levels of casual and formal requirements. For example, we’ve cruised on a number of lines that still have formal nights as well as a few that have gone upscale casual or what they call country-club. Oceania comes immediately to mind and we’ll be going country-club casual for the upcoming Caribbean venture, but we need to mindful that this means cocktail dresses on most evenings! (We can’t comment on the cruises that let people into the dining room in T-shirts and ball caps – we don’t even want to be near those dining rooms. Not our style.)
Dining out: Oh how we wish that dining out was still considered to be a treat to be cherished and prepared for by dressing a bit better than one might at one’s own kitchen table. Of course, it matters what kind of restaurant you’re going to be choosing – fast-food outlets are not restaurants. Wear what you want there! No one will bat an eye. But even if you don’t really care what you wear, it might be fun to see dining out as an actual occasion when you’re traveling. Stepping it up a bit can be entertaining, and at the risk of repeating ourselves, you’ll be treated better. You can protest this as much as you want, but it’s a fact of life. For many people – including maître d’s – dressing up a bit is a sign of respect for self and others.
At the theatre: We’ve observed that the theatre is not what it used to
be. Just last week we attended a big musical in downtown Toronto at the Ed Mirvish Theatre and we felt as if we had wandered into the economy section of a cut-rate airline. The truth is that in some parts of the world you’ll actually feel out of place if you don’t dress up a bit – and note that ballets and operas tend to have a more dressed-up audience. We noticed this in London and Sydney at the Opera House in particular. Don’t leave them off your travel lists, though; attending theatre performances in foreign cities is a real pleasure.
Obviously, you can wear whatever you want. We have noticed, however, that some people do care how they dress in general and while traveling in particular. If all of this sounds as if you will have to lug multiple suitcases, you won’t. We travel with one suitcase each regardless of the length of the trip –a weekend, one week, five weeks – it matters not. One suitcase. (It will probably be very small for a weekend!).
The Discerning Travelers 
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