Ok, here you have it, the much anticipated follow up to How to dress Part 1.

People ask me what age demographic we design for and if we make things for younger or older customers. Know this, when I say “people” I mean either editors or other fashion industry professionals - especially marketing or branding consultants. You know who never asks? The people who wear my clothes. Or simply Creative Pragmatists. Here’s why. Because every morning when they’re getting dressed, each time they’re considering a new purchase, they’re critically thinking rather than thinking critically.

Here’s the difference. Critical thinking means they’re applying their experiences, their current situation, and their preferences to weigh out what is best for them, right now and for the future. Thinking critically means you’re fixated on a varicose vein or worse, someone elses. I say worse because no one wants to be a judgey little MF.

I’m a big fan of applying reason to the reason why we do things. In case you haven’t read it yet - Almost Reckless (here)- my new book helps you break this down, with how to/action steps, and apply it to all the areas that reside outside your closet. Your career, your family, your happiness and ambitions. And if you’re like me, they’re all deeply connected and one and the same.

So how do I view dressing your age? I don’t. Here’s what I mean - if you view age and clothing in isolation, then you could look at this and think here’s your directive for age 20, 40 and 60.

But the thing is, these are three different individuals entirely, in terms of their personal style. And since personal style is an amalgamation of everything here below, I can state that hot pants here on the left should never succumb to lounge lady on the right - and someone with those loungey inclinations would have felt deeply out of place at age 20 in the shiny shorts.

So image 1 here. Can you tell her age? If I zoom in on the college paraphanalia, I’m going to guess around 20.

Or this one here. She looks straight up to me like the new version of Working Girl. That late 20-something on my subway ride, WSJ hanging out of her bag, eager to get stuff done. This is my lens, anyways.

And now here- she could be anywhere from 30s to 40s (again, my lens)- we go from the bride on a honeymoon, the navigating a wardrobe while pregnant, and having the perfect item for sticky, clingy hands.

And here we find ourselves, the kids are a bit older and we’re standing by the sidelines at a soccer match. The plaid shirt and sandals have all the chill for a busy mom in her 40s. And on the right, they kids have now fled the coop - and the pants that did all that hard work is now the one that is worn when our other 50+ group comes over for my whipcream vodka signature martini.

And now I’m approaching 60, and I’m headed to exercise class - no longer in search of the hot body but rather one that has enough muscle to strengthen bones that have gone to shit.

And here I’m imagining my life in my 70s and 80s. My brain doesn’t have to expand too far, I pick up these ideas from the incredible women I get to meet everyday now - whether IRL or in my DMs. I’ll be on the boards of various companies and get to talk about some things I’ve learned, what I know - but I won’t have to write up anyone’s reviews and for that I’ll be so damn grateful. And hopefully if I’m lucky I’ll have some little grandkids putting their sticky hands on top of the stains I’ve lovingly kept from so many years ago.

So you see, age? It’s not a thing, not when it comes to clothes.

Here’s the beauty of critical thinking. You really begin to question the rationale for things. Why would I be limited to (xyz)? Why wouldn’t I wear what I feel great in? Why on earth would I let someone else’s limited view of age limit my own?

Now, getting back to Almost Reckless…..

you can see how thinking about ourselves and our style through this lens overlaps in to real life. Because as I mentioned earlier, these questions about age come about from those within my industry. Which has me thinking, exactly what industry am I in? I know the answer to this now, and it’s amazing when you figure it out. Almost Reckless helps you get to that point, promise.