Might I Suggest Graphic
Might I Suggest: How to Dress for Confidence

As a team, we’re often fielding fashion-centric quandaries via Twitter, text, and Instagram DM, so we figured, why not make it dot-com official? Welcome to Might I Suggest, the style advice column that solves your most elusive market searches and enduring style challenges. This week, Leandra answers a question related to our theme of the month, by community member, Jen:

What should I wear when I want to feel grown-up?

Hi Jen. I love your name—one syllable, straightforward, pretty hard to botch on a Starbucks cup.

At the risk of going against the metaphoric one syllable, straightforward, hard-to-botch-ness of your name, I’m going to reinterpret your question because “feeling grown-up” is so subjective and what might make me feel like a grown-up is probably going to be different from what makes you feel like one and based on this alone, I know I’m not qualified to prescribe any form of specific medication. What I can do, however, is try to understand what you mean when you ask this question. And what you mean, I think, is to ask: what should I wear when I want to feel confident?

I assume this is what you mean because of a recent definition I have landed upon for grown-up, the noun. And to be a grown-up, I really believe, is to be yourself. I don’t mean yeah girl, all the things, work it, you do you, I mean really, yourself. Like the person, you wake up with every morning and go to sleep with every night and hang out with when the high from a caffeine kick has worn off and the hangover hangs over. So few of us endeavor to do this wholeheartedly because it takes courage — there is shit under that rug! Once you’ve unearthed it, there’s no putting it back, just dealing with it. And that courage is both a provocateur and principle of confidence.

The real kind, anyway, but I digress — what should you wear when you want to feel confident, the artist most recently known as grown-up?

Same logic on the interpretation of your question applies. The answer is highly subjective and I’m not a pharmacist, so I can’t dole our prescriptions, but I am decent with formulas, so I do recommend unearthing your confidence equation, a combination of variables multipled, or added, or divided to equate to the same, solid outcome over and over.

But first, you’re going to want to ask yourself:

What garments do I turn to when I want to feel the most like myself?

You might now be asking: How do you know you feel like yourself? It’s when you look in the mirror and a feeling of power reverberates through your body. You’re looking back at you! The real you. You like her. It’s power dressing for nuanced people who don’t wear pencil skirts or care much for shoulder pads.

The answer to this question will make up what becomes the first part of the equation.

My style lives within the tension of a supposed high-low (think denim and satin or pearls and houndstooth or linen and like, jacquard) and ripped jeans have historically accommodated the beginning of hitting the intended pressure point but the garments are more amorphous than just jeans, so for arguments sake, let’s call my answer: the tension garments.

Silk trousers and a linen shirt, for example.

Photo by Christian Vierig/Getty Images


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Western suede with impossibly clean, stark white pants.

Leandra Medine
Photo by Neil Rasmus/BFA.com
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Double-duty denim.

Leandra Medine
Photo by Benjamin Lozovsky/BFA.com


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Now divide the tension garments by a leap of faith. This requires that you muster the courage to not give up. That you make part one work in a way that works. If you feel great, but real talk is telling you that the sum of the outfit isn’t right, you don’t have to burn the house down—troubleshoot what would make it more plausible to wear. Could layering a basic cardigan over, say, your sheer dress, as styled with distinctly unsexy high waist underwear and a bra (the tension garments) make it more palatable? Presentable? Now what if you added loafers to offset the bed-li-ness?

Leandra Medine
Photo by Jojo Korsh/BFA.com
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Finally, the wild card. I define a wild card as one thing you wouldn’t assume to be true about the rules of what makes an outfit, but which you feel the urgency to try. Silk trousers and a linen shirt paired with sock shoes. Exercise clothes with regular shoes and a pair of crystal earrings. Menswear and a full face-o-makeup. The double duty denim with an evening clutch. Western suede and gala heels. The black sheer slip dress, point-blank.

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So that’s:

Best Me Clothing divided by a Leap of Faith times The Wild Card

And that becomes your confidence equation. My, how grown-up you look!

Confidence Equation Graphic

Graphics by Dasha Faires.

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