How to get dressed

It sounds a bit silly because, of course, by the age of six or seven most of us know how to dress ourselves. But I’m not talking about just pulling on a pair of pants and a shirt. Once you decide to dress well, to dress with intent – and especially in jacket and tie – you realize it involves a fair amount of planning and preparation. And if there is something I love, something I look forward to, something I relish, it is planning and preparation. I have been known to book a family vacation eight months in advance, with every day’s events scheduled and set up. But that doesn’t mean I’m not spontaneous. After all, when is spontaneity more enjoyable than when it happens in the midst of precise planning and preparation?

So yes, I am unabashedly detail-oriented. Some might even say obsessive. I arrange my shirts in my closet based on colour and pattern. Ah, but to me this is not obsessive, it’s just the most efficient way to store my clothes. It must be why I feel such kinship and draw so much inspiration from the valets and butlers of old. It was their charge and responsibility to make sure everything was in order, just so, put right, ship-shape, as it should be. To indulge in some pop psychology: I guess it’s how I try keep my own deep-seated demons of disorder at bay. But this is a post about getting dressed, not getting depressed, so let’s move on.

One of the main duties of the valet is to dress his gentleman. This usually begins well in advance of the actual getting dressed bit. The valet considers the day’s activities and picks out an ensemble he thinks is most appropriate and which his employer would most enjoy wearing. He then sets about getting all the pieces ready. In this day and age (and yes, there are valets in this day and age), he almost never actually dresses his gentleman. Without the clumsy and difficult rigours of detached collars and two-sided cuff links, most employers can dress themselves. However, the job of the contemporary valet is to have the entire outfit not just picked out but laid out in such a way as to make dressing fast and efficient. For instance, using a clothes stand (also called a butler or valet stand) the shirt, jacket and pants are hung and easily accessible. The tie and belt, or suspenders, are already attached to the pants. The socks are picked out and partially folded inside out, so the employer can simply slip his feet in and pull them up. And a shoe horn is conveniently lain across the shoes.

There is no need to go to this extreme, of course, if you are laying out clothes just for yourself. But laying out your own clothes can offer the best of both worlds: the skill and care of a valet and the joy of building your own outfit, not someone else’s. You get to choose exactly how you want to face the day, how to put all the pieces together, how to present yourself. A big part of dressing well, for me, is the joy of it. I take pleasure from my clothes and picking them out is as much fun as it is creative and expressive. However enjoyable it is, though, I strongly suggest doing this choosing the night before.

The excuse I hear from a lot of guys as to why they don’t dress well is that they don’t have the time and energy first thing in the morning to pick out an outfit. As if their closets are full of impeccably tasteful and elegant clothes but in their rush to get to work they just happen to pick the t-shirt and jeans lying on the floor at the foot of their bed. No, first you need an excellent wardrobe. But once you are on your way sartorially, I will agree that the morning is not always the best time to be spoilt for choice. You may be late for an appointment or at least in a sleepy daze. You don’t want to get to your morning meeting only to realize your tie and pocket square are exactly the same colour or pattern, like the head waiter of an up-scale pub. Plus, you will face a lot of decisions during your day, each one of them wearing you down just a little bit. As fun as it is to pick out an outfit, you don’t want to exhaust some that decision-making reservoir so early in the day.

Instead, take a few minutes before bed to prepare your next day’s outfit. Think of it as a mind-cleansing, day-ending ritual. It’s also something that can lead to a better night’s sleep because you know at least one thing is in place for tomorrow. I usually start with whatever jacket or suit I want to wear, as that will have the biggest overall impact on the outfit. Then I place whatever shirt I think works best on the valet stand and drape the jacket over top. At this point, I can start experimenting with ties. The valet stand gives me the advantage of acting as a sort of mannequin. And I shouldn’t have to say this, but don’t pre-tie your tie; you’re not seven years old. The tie will be forever creased and you won’t be able to lengthen or shorten the blade – depending on the height of your pants. Instead, I drape my tie over an end of my stand. Once I have the tie settled, I can choose the pocket square. I don’t usually leave the square in the pocket the night before as the way you fold or puff the square is, in my opinion, dependant on your mood. There’s no saying how serious or flamboyant I’m going to feel tomorrow.

I myself don’t thread my belts on to my pants in advance, mostly because I rarely wear belts. They are uncomfortable and do a relatively bad job at the one thing they are supposed to do: hold up your pants. Instead, with most of my trousers I use suspenders. These I do attach to my pants the night before. I once saw a guy – in a news video, not by peaking through his window – attach his suspenders after he put his pants on, but he’s an Italian style icon and I leave that kind of thing to the professionals.

And finally hosiery and underwear I usually pick out in the morning because they require less thought and preparation. In fact, socks fall into that pocket square folding category: an opportunity for spontaneity in an otherwise fully planned outfit.

For those interested in purchasing a valet stand, I recommend a vintage one from Kingpin’s Hideaway where I found mine at a reasonable price.