Ok, listen. We’re not seeking approval on our style when we’re out and about. We’ve established that as long as we feel great in what we’re wearing, that’s all that matters. But that’s a circular equation. We feel great when we have personal style, personal style is the outward visual of who we are on the inside, therefore when someone complements you on your style they are complementing you as a person, and that feels great. See?  

The most excited DM’s I receive are from those of you who’ve just been complimented on your style. BUT HERE’s the thing. It’s not the admiration received at a cocktail party that got you mad happy. Rather, it’s the TSA agent in airport security who said “damn….all this, damn….,” or the person at the bodega checkout line who commented “this….this….this is good,” while waving their hands around. The reason why location matters is because in some scenarios, like a cocktail party, it is often your clothing being complimented. And in others, it’s your style. Why? Because one place is usually a concerted effort, I mean, reality is we do spend more time prepping for a party. The other place - the real life places - are where most of us find ourselves every day. And when every day gets pulled off with personal style, then that means you feel like yourself - every day. And that feels good - and that shows. Even to the person you just handed over your dog for a much needed haircut.

Here’s the thing, when you have (slowly) accumulated the items in your closet that reflect who you are, then getting dressed for your life, not events, just became easy. I don’t take that word “easy” lightly, I promise. But this concept that you are either born with style or not, is utter bullshit. Once you learn some key principles, if you don’t find it easier, you will at least find it a lot simpler. I will show you.

These are my outfits. For my often lived life: grocery shopping, video calls, picking up kids, dropping off dogs….you get the picture.

You see the difference between outfits and style, right? You can see how the notion of buying items to “make three great outfits,” in your closet isn’t really tenable for your everyday life. Three days come and go quickly. You need items that weave in and out of your daily life easily. And that with the switch of a shoe, a well placed sock, or a vintage sweatshirt can change up your vibe without altering your personality.

And this is where we talk about nailing your adjectives, the three words you use to describe yourself. As Creative Pragmatists, those who balance creativity with pragmatism, the three words that consistently pop up are Chill, Modern, and Classic. These become the guiding principles for any new additions, or edits, to your closet.

So look hard at each picture of me above. Every item, not just the “look” but the actual item has a touch of ease (chill), interest (modernity) and familiarity (classic).

So something here as simple as a tee can be viewed through this lens. I’ll break it down for you:

People often make the mistakes of treating basics as, well, basic. But if you consider that basics are made to be worn everyday, and if everyday you feel basic, then that sucks. The best “basics” are those that have all the monikers of your personal style, Chill, Modern, Classic, and still be easy enough to just toss on and go. And when you get into this rhythm, you will find more comments happening from random strangers. And that’s great. Not because of the compliments, albeit they are nice. But very much because people are commenting on your personal style, which is a reflection of you. And nailing that connection between who you are on the inside with what you show on the outside is a pretty damn amazing feeling.

See? A closet filled with “style” not “outfits.”