Finding Your Personal Style: 5 Questions to Ask


When I’m at a loss for new ways to style my clothes, I still look to certain celebrities or content creators for inspiration who I feel match my style type. It’s important to reiterate that most of us sit at the intersection of various style types, and maybe dip more heavily into one or another depending on the season or time in our lives.

2. Are you truly comfortable wearing it?

As much as I love the look of super-straight jeans, every single time I’ve bought a pair, they sit in my closet collecting dust which means I like them—just not on me. Of course, we’re all entitled to wear whatever the hell we want, but the truth is, certain styles mesh naturally with our personal comfort zones.

The last thing you want when stepping out into the world is to feel awkward in your clothes—no tugging, pulling, or crossing your arms to hide what you have on. Once you’ve chosen your style type(s), understanding the fits of clothing that you like—shrunken, oversized, body-skimming, relaxed, skin-tight, etc—helps you narrow down the plethora of choices. If you don’t feel confident in it, regardless of how much you like it on the hanger, maybe you just have to make like Elsa and let it go.

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3. Do you actually like it?

Having relatively small feet for my height, I’ve always liked the way I looked better in pointy shoes that elongated my silhouette. That’s just a personal preference that I try to apply to any trend that comes along. For instance, ballet flats were all the rage this summer, and while I very much wanted to participate, I decided to hold out for styles I knew would look better on my body and ultimately make me feel more comfortable.

Similarly, I’ve never liked the look of chunky shoes, so while the “dad” sneaker was making a comeback, I steered clear of it altogether even though I did admire the way other women styled it. Don’t try to force yourself into trends if they don’t resonate with your core style.

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4. Is it realistic for your life?

Sometimes the needs of our busy lives end up dictating many elements of our style. Does your job require a long commute or running to meetings outside the office? Those things factor heavily into what we end up wearing every day. No matter our style preferences, we still need to be realistic. Consider the most worn items in your closet, which will be good indicators for what you actually reach for when you need to get dressed in the dark, then try to find elevated versions of that. Is your go-to sweater a tomato red fast-fashion find? Next season, think about investing in an accessible luxury version you know you’ll reach for regularly.

As a rule of thumb, before I purchase any new item, I always try to see if I can think of three outfits I’d be able to wear it with before taking the leap. If you’re looking to reassess your current wardrobe to identify your style, take each item out and see if you can wear it three different ways. If not, maybe it no longer belongs in your repertoire.

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5. How committed are you to trends?

This is where you have to have an honest conversation with yourself. I can’t tell you how many trends I’ve fallen victim to (hello, low-waist jeans) that I now cringe at, but that’s all just part of the process. I’ve tried very hard to convince myself that I’d wear those thigh-high white patent boots, but alas, I’m just not that girl.

The older I get, the less bothered I am by the trends that surface every week, knowing that at the end of the day, personal style is less about what you wear, but how you wear it. And remember, it’s not an exact science—be sure to have fun.

This story first appeared in Glamour UK.



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