9 Women on the Outfit That Always Makes Them Feel Confident

April 22, 2020 at 05:07AM

It’s hard to dispute the transformative power of clothes. Whether it be a perfectly tailored suit or a particularly flattering skirt, what you wear can unquestionably have an impact on the way you feel. The right dress can give you the confidence to own the dance floor, while the perfect gym kit can have you feeling unstoppable during a workout.

Although some might think it sounds frivolous, wearing clothes you love can do wonders for your mood and confidence. And now more than ever, it’s important to continue to do the things that put a smile on your face.

With this in mind, I set out to discover the kind of clothes that have the ability to empower us, asking nine stylish women which outfits make them feel most confident. As you’d expect, each woman had an entirely unique answer, from flowing dresses to power suits and vintage finds. Evidently, confidence comes in many forms, and as you’ll discover below, it’s completely unique for everyone.

“The outfits that make me feel the most confident are the spicy ones. You know, the less obvious pairings that give you a thrill. For me, seeing clothes as a fun and spontaneous expression of yourself matters. I mean, I know we’re inside a lot at the moment, but for my savoured grocery store sojourns, I’ve been kitting up in some of my favourite designer dresses (ones I would normally be saving for special occasions only!) and paring them with a low-key sneaker. Now #iso or not, I’ll always have a soft spot for a Superga and floral maxi.” 

“I feel most confident in a bold vintage piece, and there are a few in my closet that I’ll never be able to let go of. I can’t pick just one. I love a good statement vintage piece—such as these leather pants—because the fit just moulds to you and you’re the only one in the world with that exact piece and fit.” 


“My most worn outfits are midi dresses that highlight my features and figure instead of hiding it. From high-waisted skirts which accentuate my waist to bright and bold colours that compliment my black skin, I’m at my happiest and most confident when wearing outfits that not only fit and feel comfortable but feel like me.” 

“Style and clothing for me are a form of art where I can get away with expressing myself in my truest form. It is related to my personality. For me, wearing an oversize suit exudes style and confidence, as it contrasts masculine power in its sophisticated cut against my feminine and passionate character!” 

“I definitely feel my best in a good old vintage dress. I discovered my style in the thrift store growing up, so wearing these truly amazing dresses really takes me back to a time where I was discovering not only my style but also my confidence!”

“I feel most confident in the right pair of jeans (not too tight) with a light flare on the legs and a fitted waist. I wear them with heels, a T-shirt and a blazer, it’s a casual but very effective outfit, as I don’t necessarily need to dress up to look chic. It’s a great confidence booster.” 

“The outfit I feel most confident in is definitely a cute dress and flip-flops. It’s feminine and comfy at the same time and super easy to wear. I wear the combo when going to meetings, going out, family dinners, events, etc. Basically to any occasion.”

“What makes me feel most confident is when I wear a satin dress. Satin is empowering,  elegant and comfortable all at once. It’s one of my favourite things to wear. I love the non-threatening polite and gentle look. I see myself including a piece of satin in anything I wear.” 

“I think the outfit that makes me feel confident is the outfit that I feel comfortable in and that makes me feel like myself. The outfit that helps me achieve this is a perfectly tailored suit. This spring/summer season, I will be looking for colourful suits with shorts.” 

“My go-to outfit when I need that extra boost of confidence in business is definitely a white crisp shirt, white slingbacks and a pair of suit pants. My favorite ensemble is the Capri shirt from Toteme, comfortable ELENA slingbacks from Sania D’mina and these brown pants from Moon Choi Studio.”

Next up, the biggest S/S 20 fashion trends you need to know. 

Author Zoe Anastasiou | Whowhatwear
Selected by CWC

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