Feeling Good While Feeling Bad - Why Outfit Habits Matter...

I took a trip to my local clinic this morning. Spoiler alert: I have the flu.

Needless to say, my outfit today was mostly about comfort but still elevated. I was wearing a dark gray pair of moleskin-ish trousers by Cremieux (with a fair bit of stretch), an olive green deep-vee undershirt, an olive green corduroy button-up shirt (untucked) by UntuckIT, olive and burgundy over-the-calf merino wool socks, tan leather sneakers by Lems Shoes, a gray herringbone flat cap by American Hat Makers, a camel overcoat by Michael Kors, burgundy Nappa leather gloves by Fort Belvedere, along with a necklace and rings with olive, burgundy, and tan accents.

As I was preparing to leave, paying my copay and getting a receipt, a very young but very attractive lady was checking me out. As she did so, she commented that she, "[Loved my] clothes! They're very cool and, like, old money." This wasn't the only compliment I received on my outfit - the bar for patients at a local clinic is understandably low - but it was my favorite.

There was no one else really within earshot and no lead-in comment; it was just a simple compliment she decided to pay me in that moment.

Sincere compliments are always nice, but they're extra nice when they come from someone you would have likely been enamored with a couple of decades ago - and they're doubly nice when you feel like crap and put very little thought into your outfit.

Which brings me to my point about outfit habits and why they matter...

It's tempting, and relatively easy, to throw on a pair of pajama pants or sweat pants and an old t-shirt and whatever coat or jacket is closest to the front door on your way out to visit the clinic.

These pants aren't my favorite. They're not the best quality and the legs are a bit too skinny but they fit me well and are comfortable for normal wearing or if I just want to lie on the couch for a while. I knew there was a good chance I'd be pulling my pants down for a syringe or two, so I wanted to go untucked - and grabbed the olive green corduroy shirt. Of course, it's cold outside so I went with an olive undershirt to layer - but a deep-vee since undershirts shouldn't be seen. I could have gone with gray socks but the olive and burgundy pair were right there and I know I have accessories that complement them within my options for jewelry and gloves. I spent less than five minutes getting dressed this morning and really only made two decisions: the pants and shirt. Everything else in the outfit just came together out of reaction or instinct or, perhaps most accurately, out of habit. I could have gone with any of my three overcoats - they all would have worked with the rest of the outfit - but I went with the camel because it's the only one that has a dedicated pocket for gloves.

I put, effectively, no more thought into getting dressed this morning than someone who throws on a pair of sweat pants, a graphic t-shirt, and a random coat or jacket. And, yet, casual observers might have thought that I put significant time and planning into my outfit.

So, what are the habits that can enable this ease of dressing well?

Making sure all the clothes in your closet fit you well.
Knowing exactly what you have in your closet - from underwear and undershirts to tops and bottoms to outerwear to accessories.
Practising putting outfits together - even on unnecessary days - so you already know which items work with others in your closet.
Practising wearing outfits spanning all levels of formality, not just one or two.

These habits allow you to put together well-looking outfits even on your off-days, when you aren't taking the extra time to plan your outfit. There's a human tendency to choose easy, familiar paths. A lot of men are, for example, comfortable either in jeans and a t-shirt or in a suit - but they're not really comfortable with outfits that fall between those two extremes because they don't practice wearing them. When you reserve certain accessories - such as jewelry, pocket squares, or gloves - for special occasions, you may not have honed the skill of wearing them properly with everyday outfits.

The three biggest keys, in my opinion, to a harmonious outfit are a proper fit, proper function, and a good aim for formality. The first two are, admittedly, obvious and - when done poorly - make any outfit simply look a bit off, at best. The last one, though, is where these outfit habits shine. You don't want any single piece of your outfit to look significantly more or less formal than the rest of the outfit. And the only way to learn how far up or down you can dress certain items is to practice that skill, in both directions, with every type of thing in your closet.

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