Dressing Your Age VS Dressing Timelessly

I think we’ve all heard of these concepts before. I first learned about the concept of dressing timelessly from watching videos on minimalism, specifically on how to create a capsule wardrobe for minimalist living. Those videos always talked about how you should dress timelessly so that you never have to ‘fall for trends,’ and how you should know your best colors so that you can keep a limited color palette for maximum outfit versatility.

Dressing my age, on the other hand, is a concept that I’ve really only understood recently from watching style analysis videos, usually about teenage or young adult characters. In those videos it’d often be pointed out that the characters don’t “dress their age” and that they look like they’ve been dressed older than the characters are supposed to be which… well, it made me realize that I don’t dress my age.

You see, dressing for my age and dressing timelessly together doesn’t work. So why is that?

The expectations of women as they age

I can’t talk about men’s experience with aging and the expectations they face around that, as I’ve never experienced being a man. All I can talk about is my experience as a young (cisgender) woman and seeing how the expectations of women in general have been placed on myself, my peers, women I know, and women I’ve seen in media.

The expectation is that when you’re young you should be outgoing, adventurous, and willing to explore new ideas, and that as you get older you should become more practical, organized, and that you should settle down into a particular style. I understand why these expectations exist, especially for teenagers and young adults, because that age range is often filled with issues around identity. It’s around that age that we’re expected to start figuring out where our identities stand, who our peer groups are, what cliques or groups or subgroups we belong to, and our clothing styles are an outward reflection of that.

Trust me when I say that I’ve tried a lot of different looks while going through the process of understanding my identity. When I was 13 I tried to be a hipster, 14-15 a goth, and at 16 I almost only wore business casual clothing (and it was around this point where people started asking me how old I was, because yeah I looked young, but I didn’t dress young).

I have to admit, I loved that once I started wearing dressier outfits people weren’t sure about how old I was, because I was one of those kids that was always called ‘mature for their age’. I’ve tended towards being a fairly independent person, and since I never felt like I fit in among my peer groups, I liked that I looked older.

So I kept dressing that way.

Okay, so I don’t wear blouses every day anymore. In fact, blouses make up a significantly smaller portion of my wardrobe now, but I learned how to ‘dress timelessly’ so I still have the same effect. And that’s because you can’t really dress timelessly as a teenager/young adult (I’m talking the age range between 16 and 24) and dress your age. We’re expected to experiment with trends, to try out weird and wacky combinations, and in the age of social media, a lot of teenagers have actually become trendsetters with their fashion choices.

And here I am with my almost entirely neutral colored closet (I make an exception for red because it’s my favorite color), my blouses and blazers, my love of timeless looks and outfits that are directly inspired by Audrey Hepburn, and I see a lot of these trends and say “that looks so cool, but it’s not for me” and that’s okay.

At the opposite end of the spectrum is my mom. Don’t get me wrong, she’s a very practical and organized person (I envy her organization skills and her work ethic, she’s my hero), but she also has a very youthful energy and she loves to experiment with different colors, textures, and patterns with her outfits. Where I’m neutral tones, she’s the rainbow, where I’m subtlety and minimalism, she is sparkles and vibrancy.

So what does that mean? People assume that she’s younger than she is! You can imagine the confusion that we sometimes get when people learn that we’re mother and daughter.

Neither of us dress our age, and for opposite reasons.

Should the expectations change?

I’m going to be honest, I don’t really care if a person dresses timelessly or not, as long as they’re happy with the clothes they wear. But the expectations of how a woman should look her age is something that I care about.

And the reason why I care about that is because for a long time, women were told that we become obsolete past a certain age. And though we’ve made a lot of progress towards equality, some of the remnants of those ideas are scattered about in the way we talk about things, especially appearance.

How many adult women are told that they shouldn’t do their makeup a certain way, because it ‘ages’ them? I remember being a preteen girl and seeing in a magazine that older women shouldn’t wear dark or matte lipstick colors, because it’s ‘too heavy’, when that has to do with a person’s body type and facial features rather than their age.

What are your thoughts on this? I’d love to hear them, so leave me a comment if you feel like sharing your ideas on this topic. Thanks for reading, and thanks to my friend Samia for helping with line edits on this post.

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