trying too hard style fashion

The concept of “trying too hard” irks me. People are constantly being criticized for putting forth minimal effort, and yet we censure them for being overly enthusiastic, too. Talk about a lose-lose proposition.

And yet, I’ve gotten several reader questions about “trying too hard” stylistically, and I understand why. When I was 13, I felt certain that simply OWNING and WEARING cool clothes would make me cool … but when I got my hands on an entire Esprit ensemble and wore it to school, I was still shunned. And the feeling I had? Trying too hard. Specifically trying too hard to fit into a group that didn’t want me, trying too hard to adopt a style that had nothing to do with my own tastes, trying too hard to be someone I’d never be.

As an adult, I’m still susceptible to the delusion that buying and wearing cool stuff will make me cool. But I’ve learned that even cool items can become uncool if they clash with the wearer on a personal level. In my opinion, there are three main actions that will trigger that “trying too hard” feeling:

  • Wearing something that doesn’t feel like it aligns with your personal style
  • Dressing specifically to attract attention or garner compliments
  • Crafting looks that feel over-the-top or excessively showy to you

We all do these things on occasion, and they are healthy and normal. How else are we supposed to expand our wardrobes and allow our styles to evolve if we don’t wear items that fall outside our comfort zones? What’s wrong with wearing something we know looks amazing and hoping that friends will dish out a few much-needed compliments? What fun is life if we don’t get glam and dramatic sometimes? Making a habit of any of these three, though, may cause you to feel off-kilter, lost, and potentially like you’re … well, trying too hard.

That said, my guess is that folks who are frequently plagued with worry about their levels-of-stylistic-trying may have to deal with peer scrutiny, a vocal and judgmental friend group, or some form of outside input that creates fears of dressing “the wrong way.” Dealing with someone who verbalizes negative opinions about the dressing choices of others – not necessarily yours, but even celebs or strangers – can give a gal a complex. Because in a neutral or supportive environment, showy outfits generally generate discussion and neither the wearer nor the observers feel compelled to deem them “good” or “bad.” A neutral or supportive environment will often encourage self-expression and see behavioral changes as points of interest instead of potential threats. But a judgmental environment will cause self-consciousness, doubt, and fear of retribution for branching out or rocking the boat.

I believe that confidence is the key to overcoming concerns of trying too hard. If you have a highly vocal peer group to contend with, push yourself – and them – a little at a time. If an entire outfit is too scary, wear one or two pieces that you feel might verge on “trying too hard.” If they draw comments, deflect them with humor. One of my favorite ways to defuse situations is to laugh along with the commenter. “Hahaha, I know! Isn’t this WILD?” tends to work wonders. You’re acknowledging that you’re doing something different, reinforcing that you’re enjoying the exploration, and showing that you have no intention of being cowed into some sort of apology for your tastes and stylistic choices.

Now, if your internal voice is putting a damper on your efforts to explore new avenues of style – if it’s just you who is cooking up fears of trying too hard – here’s my advice: Fake it. Wear items or outfits that feel uncomfortably bold, and pretend like you totally own the looks. Whenever you pass a mirror, look at yourself and say, “I look AMAZING in this!” Walk tall, mind your posture, and smile. Keep it up, on a schedule if necessary: Twice a week, then three times, then four … Eventually, you’ll feel as confident as you look and those worries about trying too hard will begin to dissipate.

Image courtesy Dave77459.

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