Are there any clothes you just can’t wear?

Well, “can’t” is the wrong word – obviously nothing’s preventing you from donning flat-front khakis, or a bow tie, or a high and tight hairstyle, for that matter.

I’m talking about the items you put on – whether off the rack at the store or pulled from the back of your closet – and just think, “Nope, no. Uh uh. Get. It. Off. Me.”

For me, it’s dress shirts. If it buttons up the front, I want no part of it.

That’s not to say I don’t own button-front shirts. Quite the opposite, in fact. I’ve bought them time and time again, thinking, “This time….this time, it’ll work.”

Because, and I know you feel me on this, they look so good at the store! That petal pink Ralph Lauren OCBD I snagged at the outlets a few years back, when Kate Middleton’s tucked-in preppy style was showing up on every women’s fashion blog? Very cute on the mannequin.

And when I got it home and just couldn’t figure out how to wear it? My tailor tagged in, adding darts in the back to create a more form-fitted look. That expense – small as it may be – taunts me every time I pull the shirt on, when I button it all the way to the top…then give myself the side eye from every angle in the mirror and immediately pull it off again.

But there’s a difference in feeling outside your style comfort zone and simply uncomfortable.

Not sure what’s not you vs. just what you haven’t figured out how to wear? Ask yourself these questions:

1) Have I tried it multiple ways?

It’s important to experiment. Maybe you don’t like how a bow tie looks when it’s dressed up with a suit, but what about with slacks and a sport coat, or with dark, straight-leg jeans and the sleeves rolled up. Especially once you’ve brought an item home with you, you might as well do your due diligence and see if there’s a way you can make this alien item work for you.

2) Are other people wearing this?

If you’re considering a trend that simply hasn’t made its way to your city, or your circle of friends yet, your style discomfort may be a case of “One of these things is not like the other.” If that’s the culprit, I’d encourage you to take that trend for a spin anyway – and forge the path for your pals, rather than following it.

3) What don’t I like about it?

If it’s a fit issue, take it to the tailor, then give it another try. You might find that whatever problem you had with the style has been fixed by improved fit.

Or, you might discover the item in question is still a no-go, as was the case with my lady OCBDs. For me, I realized the problem was that button-fronts don’t make me feel feminine. I’d rather get my structure from a blazer (with a tank underneath) or a pencil skirt (with a luxe t-shirt tucked into it).

And since I inevitably smear red lipstick whenever I wear it, I didn’t want to counteract the masculine lines of the shirt with too much overconsempating. But hey, that’s just me.

Tell me:

Have you ever had to talk yourself into – or out of – a piece of clothing in your closet?

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[Photo credit: Books Direct]