Ask Yourself These 3 Questions The Next Time You’re Stumped by Style

Ask Yourself These 3 Questions The Next Time You’re Stumped by Style

Time to play Style Inspector Gadget
three images of trendily-dressed men

By Megan Collins | Last Updated: Apr 3 2024 | 3 min read

Are there any clothes you just cannot for the life of you figure out how to wear?

I’m talking about the items you put on — whether you’re shopping at the store or pulling from the depths of your closet or drawers — and think, Hmmm, I like it, but…no, not for me.

It can be easy to think: Wide-leg pants / high top sneakers / workwear jackets just aren’t for me.

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

Not sure what’s not you vs. what you just haven’t figured out how to wear with confidence yet?

If you want to learn how to be more fashionable, ask yourself these 3 questions:

They’ll come in handy the next time you’re struggling to figure out how to wear a piece of clothing you like but has you stumped.

man in park wearing a grey turtleneck, olive military jacket, wide-leg pants, and white sneakers
image: @callumscott13

1) Have I tried it multiple ways?

It’s important to experiment when expanding your wardrobe repertoire. 

Maybe you don’t like how a granddad collar shirt looks with chinos (too boy band music video), but what about trying it with dark, straight-leg jeans and the sleeves rolled up? Or paired back to a summer-weight suit for a casual beach wedding

Especially once you’ve actually bought something and brought it 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.

couple walking down the street wearing coordinating brown outfits. the man is in a brown cardigan and brown pants, while the woman is wearing a satin brown jacket and khaki-colored long skirt
image: @mesyeuxsurtoi

2) Are other people wearing it?

If the item in question is a trendy, fashion-forward item, the issue could be a lack of references and representation in your own day-to-day life.

Maybe the trend hasn’t made its way to your city, or your circle of friends, yet. If so, your discomfort might be a case of Tall Poppy Style Syndrome. 

So, if uncertainty about playing the trendsetter is the culprit, consider feeling the fear and wearing it anyway. Take your new piece for a spin and forge the path for your pals, rather than following it.

You might be surprised by the compliments you get…and the outfits you inspire.

young man in fitting room taking a selfie in the mirror, wearing a cream beanie, black leather jacket, v-neck sweater, necklace, off-white jeans, and black boots
image: @paris.haven

3) What don’t I like about it?

Maybe it’s the fit that’s making you scratch your head. Are these pants too short? Should this shirt be so poufy?

If so, take the item to the tailor, then give it another try. You might find that whatever problem you had with the style has been fixed by the improved fit and feel.


After all this, you might discover the item in question is still a no-go.

And if that’s the case? First, pat yourself on the back for trying something new (or trying to try something new, anyway). Then, sell or give away the piece in question. One man’s failed trend could be another man’s treasure.

Even if it doesn’t end up in your regular rotation, you’ve learned something about your style, and that’s a win.


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I started Style Girlfriend to help guys look, feel, and act their best.