Today, on my way home from picking up bananas and a latte (don’t ask me about the health-related inequalities there), I saw a woman cross my Chicago street wearing slightly sheened polyester leggings (black, but looked a touch blue because of the workout-worthy sheen), a North Face vest, and a long sleeve t-shirt with patent leather, elastic-shaft, high-heeled boots.

Naturally, the first thought was “That’s a wholelottalook there, honey.”

My second thought: “Why do you look so bloody uncomfortable? Typically, when one wears such a bold outfit, they exude *ahem* sometimes too much confidence.” But you could tell just by looking at this woman that she was uncomfortable. She didn’t know why she was wearing what she was, much as we wonder why anyone wears something they don’t want to, much less a spandex & fleece cocktail like that.

So the rest of my way home, I thought about what would possess me to put on something that I would never dream of feeling comfortable in, aesthetically or physically. At the time, I was wearing jeans, an old Bill Blass silk blouse, and my black trench coat with gold flats. The only thing I could think to do was to figure out why I got dressed this morning:

• I knew it’d be a relatively sedentary day…
• But I also knew I needed to go to the store, so I couldn’t wear sweats.
• Fashion-wise, the blouse-y-ness of this top is not only really comfortable, but it’s very casual-luxe.
• The jeans were straight leg, as to give me lots of room for legs, but also keep a good shape down the leg line.
• The gold flats were unnecessary, as far as comfort goes, I threw them on because a) they’re shoes and b) they look great with what I’m wearing.

So then I imagined if I were the woman crossing the street. The only answer I could come up with for “Why would I put this on in the morning?” was:

Because I think I’m supposed to think it looks good.

Think about it… The boots (she was heavier, so a stretch-shaft boot may have been her only option, speaking from experience), the North Face vest (how long has the upper-middle class claimed that those were on-trend?), the sheen-y leggings (as pants, no less).

All of these things, to me, point towards “I’m trying to be trendy, but have no idea why, or how.”

This is a big theme for women, I think. Particularly women who are on that cusp of “young woman” and “woman woman”. How young is too young? Is it okay to not dress trendy, or will it immediately make you look like a frump? Should a 35 year old woman err on the side of matronly, or youthful!?” So many questions, and no go-to for answers!

Forgive me, Rachel Bilson, but you’ve got
an awful lot of “trend” going on here. Photo.

Trends, ladies, are not the end-all, be-all of style. The big difference between sweating a trend that you’re uncomfortable with, and appearing effortless is just that – effort. The amount of effort you put into dressing yourself always shows. You know what else shows? The intention behind the effort. If you’re throwing on strong shoulders and leggings and lace up boots and oversize sunglasses and sequins and plaid… You’re not wearing the clothes anymore, they’re wearing you, and you’re the pawn of the trend.

It’s one thing to like a trendy piece of clothing, it’s quite another to like a trend.

If you find what you like (honestly and truly like, appreciate, admire, etc.), and stop when you feel satiated with “trend” (if that’s your thing), it will appear effortless. This is a simple formula that so many women over-think, and over-thinking is the real killer of style.

…On the other hand, isn’t it somewhat of a right of passage?

I’d say yes. Over-trending is the adolescence stage of an ever-growing style. Everyone has to go through it. You have to reach “maxed out” before you can achieve “balance”. It’s about knowing where your own boundaries are. Post-adolescence over-trending? Less understandable.

How can you prevent it? Check yourself, forced ye wreck yourself.

The next time you’re in The Bon Macy’s, and you’re leaning towards that hyper-sequined shift dress with shoulder pads… Think: Why do I like this? Do I like this enough to describe why I bought it to the handful of friends who will just stare, mouth agape, until I say something? Will I feel comfortable and confident walking down the street in this?

If “no” is the answer to any of those, or you can’t come up with a “why” – you know what to do. Put the hanger down. Step away. Here’s my trick: Put the hanger back on the rack, and continue your perusal. If you can’t get that sequined, shoulder padded, sheath dress out of your mind, grab it on the way out – but be sure your longing is less curiosity, more passion.

Bottom Line: Why are you wearing it if you’re not in love with it? Not only will that save you dollars, but it’ll save you the grief of walking outside in something you’re not 100% you in.