Ask Colin: Dressing Oneself

Hello Colin,

I’m writing you because I’ve just been hired for a new job and after many years of working from home my wardrobe isn’t really suitable for what I’ll be doing (going to other offices and consulting with clients). So I need to buy some new things in the next couple weeks.

I’m looking at websites and stores, though, and I’ve realized that I don’t really know what my style is. I’m not a fashionable person, and have always kind of just taken free t-shirts when they’ve been given to me, bought some baggy jeans and worn them till they were too filled with holes to be appropriate, and left it at that. I have a suit jacket that doesn’t fit, too.

This sounds stupid even as I write it because it seems like it should be obvious, but how do I figure out what my style is? How do I use that knowledge to buy clothes that will work for me and how do I get past this fear I think I have about buying clothes for myself?

Sincerely,

Dameon

Hey Dameon-

I recently started using a few skincare products.

They aren’t anything fancy, and they aren’t a big investment—maybe $20 every few months, as the little bottles and tubes are used up—but they’ve made a big difference for my skin as I travel from climate to climate.

A very kind friend advised me on this topic, after bulling through some reflexive pushback from my end. I’ve always discounted the whole concept of skincare as some kind of money-grab and didn’t see the point. I knew in a general way that there was more complexity to it than “lotions and sunscreens exist,” but I never took the time to learn beyond that superficial and wildly incomplete understanding.

After trying a few little things that she had on hand, with her encouragement and assistance, I realized that part of why I’d always avoided the field was that I knew so little: I didn’t even know where to start. That fear of the unknown led me to believe that the whole industry was probably hokum, or something close to it, and that it was either too expensive or too nonsensical for me to care about, so I was better off just avoiding it.

There’s still plenty of room for skepticism when it comes to any industry, to be clear, but I’m glad I made it past that mental barrier. Not because skincare products are necessary for everyone, but because it was an aspect of life that I had psychologically blocked and decided I wouldn’t even look at, wouldn’t consider exploring; which is counter to the way I approach essentially every other aspect of life.

I bring up this recent, personal experience because I think there’s a chance that clothing might currently exist within a similar blindspot for you, and I think it’s wonderful that you’re considering taking a closer look, despite feeling like you’re starting from nothing and thus don’t even know what you don’t know, yet.

It’s not a silly question or concern, in other words: it’s a very valid one that gestures at a personal desire for growth, and the humility required to put yourself in the role of the student.

That said, some thoughts about learning to dress oneself:

One concept I’ve found to be illuminating in this space is that there’s a difference between style and fashion.

Roughly defined, style is a person’s individual aesthetic and fashion is a collection of trends and norms that determine, in part, what’s trendy, what’s on shelves, and what all the celebrities (and often, subsequently, the rest of us) are wearing.

Runway shows generally feature one-off designs (haute couture) that frequently go on to inform what’s in stores in the coming months.

The business model of the fashion industry is broadly oriented around seasons, with each season introducing a new set of styles, those styles partially based on what trendsetters around the world are wearing, partially predicated on the whims of fashion designers, and partially determined by environmental variables (weather, supply chain considerations, etc).

Seasons were originally meant to give clothing companies the chance to hit consumers with jackets and parkas and shorts and sundresses at the right moments, based on actual weather-related seasons. But the term has since become a mechanism through which such companies can refresh their offerings, hoping to sell more clothes and accessories to more people at a far more regular cadence, leading to a sales model that is often called fast fashion.

You can try to stay in fashion and adhere perfectly to the templates provided by your favorite brand, or you can try to ignore fashion and focus entirely on your own internally defined aesthetic sensibilities. In both extreme cases, though, you’ll almost certainly fail, as those templates will be selected based on your sense of style, and your own concoctions will be made of garments created by the fashion industry. Your sense of what looks good, too, will almost certainly influenced by what’s on shelves, who’s wearing what in movies and magazines, and so on.

These seeming dichotomous elements of the clothing world, then, are inextricably connected, and understanding that connection can allow us to be aware of where our clothing biases come from, how we’re being marketed to and manipulated, and how we might adjust our buying habits and other behaviors to avoid the most damaging elements (psychological, economical, and environmental) of this space.

A good place to start when sorting out your own sense of style is to do some active research: looking at the photos in relevant magazines, for instance, really paying attention to what people are wearing and taking stock of what you like in terms of aesthetics and vibe. It’s also worth noting what looks good on people with whom you share a similar frame and face-shape.

From there, do some online searching for similar items to assess your range of options, but look for stores that sell the kinds of things you like and that you think might look good on you. Go try things on, when possible. Keep your budget in mind, but also allow yourself to try things that are out of range, currently, to see how they suit you: there’s a good chance that a cheaper variation is available, elsewhere.

As you’re going through this process, think about what your clothing says about you to other people and how different clothes make you feel.

You may be naturally attracted to clothing similar to what you wear now, but something a little more fitted, a little more buttoned-down rather than casual, might look spectacular on you, and the social feedback you’d get wearing such things would help you feel more comfortable and confident, changing your perception and preferences.

It’s also possible that there’s a variation of what you’re doing now that can be tweaked a bit to be more socially acceptable in more situations, but which will still allow you to feel like “you.”

Just be careful not to accidentally lock yourself into one look forever, just because a more style- and fashion-ignorant version of yourself started out wearing such things. Think and experiment broadly, and try things even when you experience an initial psychological resistance to doing so (perhaps especially in those cases).

Since you’re looking for clothes that you can wear to work, there will likely be certain expectations and rules delimiting your range of options.

You can express yourself within those limitations, but it’s a good idea to try to do the fundamentals by the book, at first, and to make tweaks as you become more aware of your true preferences and become more comfortable with your overall relationship with your clothing.

Start out by learning the broadly accepted “correct” way to wear a suit jacket and tie, in other words, so that when you decide to break those rules, you’re doing so intentionally rather than accidentally.

As you go through this process, it’s also worth paying attention to what sorts of businesses and business models you’re supporting with your purchases.

A lot of clothing companies, particularly those that fit into the aforementioned fast fashion category, have inbuilt issues with their labor practices and their ecological footprint.

It may be that such companies are the only real options you have right now, geographically or financially, or that such issues are not a focus for you.

That’s understandable. But do be thinking about the structural integrity of your clothes (build quality and expected lifetime), what sorts of practices you’re supporting, and who might be hurt or uplifted as a consequence of you giving your money to one business over another.

We’ve all got different priorities and circumstances, and there’s no inherently correct or incorrect way to shop for clothes. But all else being equal, it’s generally a good idea to aim for less of better—a smaller, higher-quality wardrobe—over a sprawling-but-not-great version of the same.

Part of that “better” descriptor might be ensuring that you’re supporting positive causes and entities, rather than funding models that are immensely wasteful and which charge exorbitant prices to have the right logos affixed to them.

What’s most important right now, though, is giving yourself permission to be someone who is capable of appreciating, knowing about, and even liking clothes, even if they’re not something you plan on thinking about most of the time.

This change in mental stance will help you see past blind spots, making it easier to learn about the industry, what fits, styles, and colors suit you, and how to utilize that knowledge to build yourself a flexible, you-shaped wardrobe that aligns with your personal and professional needs, aesthetic sensibilities, and budget.





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