11 Chic Wardrobe Essentials If You’d Describe Your Style As “Feminine Tomboy”
Why does this feel like our style awareness was just cracked wide open?
by The Candidly Team
We are constantly urged to “come up with words to define our personal style!” on fashiony websites, which apparently makes shopping, getting dressed, and living, so much easier.
And now, made viral on TikTok, Allison Bornstein tells us to think up three words, three adjectives to be specific, which we should all use as a touchstone to define exactly how we want to look and feel in our clothes.
We tried this method, and we failed miserably. Some days were CLASSIC CHIC NEUTRAL, other days were WEIRD TIMELESS UNDONE. We just weren’t smart enough to find definitive words that we could rely on, day after day, to encapsulate our perfect relationship to our personal style.
And then one day, we were going through some old photos of Meg Ryan for some other article completely unrelated to this one, and all of us gasped at how her style is basically our dream style. And yet, all of us have wildly different styles from one another.
So first, here are the Meg Ryan photos that sparked this entire idea:
What’s the common thread here? Why do we all love this? What even is this style? And why, despite us all having vastly different taste, does it feel so exactly, universally, how we want to dress?
No, really. We’re asking. Because we don’t know.
What we do know is that we gave this style a name:
Feminine Tomboy.
Maybe this term is already out there (“You can’t take it back. It’s already out there! Name that Meg Ryan movie) but using this phrase in Pinterest (which is where we found almost all of the photos below) was like finding some kind of Rosetta Stone of perfect search terms to yield 487 thousand outfits that we all want to own and wear immediately if not sooner.
We can’t bring you all 487 thousand, but we did narrow down 11 outfits that made us gasp, have deep discussions about why we gasped, and motivated us to find many, many real-life, mostly affordable pieces that one could buy this very moment to recreate those very outfits.
We have to say the first look sort of says it all, but we feel strongly that you’ll take some ideas, however small, from each ensemble.
Strong but soft. Bold but effortless. Polished but casual. Girlish but androgynous. All true.
Though nothing quite sums it up better than Feminine Tomboy, right?
Ok. Let’s begin.
Why this works:
First: effortless. Everything just sort of hangs together perfectly. It’s the sort of look that seems like it would feel like we never changed out of our loungey house clothes, and yet, it’s pretty much proof that when each piece is chosen correctly, we can do slouchy and still look tailored and chic.
How to recreate it:
For something this simple to come off so polished, every single piece has to be a star. Starting with the linen pants, which should be wide-leg but have a nipped, high-waist so our legs look a mile long. We love THIS pair, because to the rest of the world, we look like we’re in proper trousers, but we feel completely unrestricted.
For a tee to not be stiff and unflattering, you have to go with a wispy, soft fabric and a perfect length that will also sort of narrow you. THIS one is excellent, because despite not being tight (which obviously feels amazing), it’s also skimming and the ideal, not-too-spacious fit.
A sling bag is one trend we can get on board with, because it is so practical, so nonchalantly chic, and so comfortable (yes, a bag can and should be comfortable, and crossbody is the only comfortable way to wear a bag). THIS is our current favorite. It’s from Madewell but looks better than designer.
And finally there’s the nothing-like sandal that’s so minimalist, you scarcely know you’re wearing it. THIS incredibly chic shoe is astoundingly comfy and balances out all the looser layers up top, making us look “styled” instead of lazy.
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Why this works:
In the reality of day-to-day getting dressed, 9 times out of 10 we choose “cozy things” like sweats and sneakers. But a part of us is always a little disappointed not to realize our inner dream of looking more put together. This look lets us do both by blending those softcasj (a new term we’re coining right now) with clean-lined, expensive looking pieces. It’s a balance that speaks directly to our soul.
How to recreate it:
We’ll start with the sweatshirt, which sounds so easy but so many let us down. THIS one is soft in ways we haven’t known before and doesn’t bulk you up like so many sadder sweatshirts do.
And then, of course we add that sleek, edgy leather jacket. We can’t and won’t stop talking about THIS one from Quince, because it’s $150 and it’s perfect.
A lightweight, loose-fit trouser is a staple for anyone who got a little giddy when they heard the term “feminine tomboy.” THIS pair is flattering and chic, and has actual stretch.
And, of course, it remains limitless what you can do with a pair of Converse. THESE Converse.
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Why this works:
There’s something so comforting about being draped in an immense piece of knitwear and a baggy jean. The fact that this is a “style” is also deeply comforting.
How to recreate it:
Start with the oversized sweater. We found THIS one on Amazon that comes in a bunch of perfect neutral colors, and we’re pretty obsessed. Make sure to half tuck it so you see a glimmer of that belt buckle.
All baggy jeans, we’re sorry to say, are not created equal. Yes, you want that chill, drapey leg, but you don’t necessarily want them so loose in the bottom that they flatten your butt into oblivion. THIS pair from Madewell nips at the (high) waist and glides over your natural curves, so you get the best of all fits.
Another Amazon find was THIS puffed crossbody bag, which weirdly is going to make your whole outfit look more expensive. It just has that carefree, semi-designer vibe.
Nothing completes this look more effectively than a minimalist pair of sunglasses that have the single most flattering, face-framing shape. The best bit about THESE is that they’re $50 and look like they cost 5 times as much
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Why this works:
We don’t want to go to our grave without finding our own ultra-femme version of a full-on tuxedo look. We just don’t. You?
How to recreate it:
It starts of course with the suit itself. THIS blazer is perfectly cut, relaxed, yet stretchy so we still get that ideal nipped, silhouette.
THESE matching pants are gorgeously stretchy, and they’re excellent on curves.
THIS shirt is the gold-standard in terms of crisp, chic button-downs, and it’s as gorgeous tucked into a suit as it is tied up with a pair of jeans.
And, we love THIS lug-sole lace-up, which dresses up better than many of our heels.
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Why this works:
We wanted a smart vest ever since we can remember, or maybe since we saw Meg (once again) parade hers all over the Côte d'Azur in the movie French Kiss. In any case, it’s one of the more flattering, more interesting things we can wear with its dipping v-neck and skimming shape, and yet we forget about it because it just seems so formal. And that’s what’s so great about pairing it with jeans and a cap. It’s the smart city look we all hold in our imagination. And all this time, it’s been wildly easy to realize.
How to recreate it:
This one is simplicity itself.
Find a vest with a chic shape. We love THIS one because it has the right fit to make you look instantly tailored and sophisticated, but in a casj way.
For the jeans, we opt for THIS same relaxed pair mentioned above. We’re creating a capsule here, people!
Any cap that holds your heart will do, but we’re a little mad ourselves for The Farm collection by Goorin Bros HERE.
And now is 200% the time to bring Doc Marten’s back into the mix. THESE are our favorites. See proof of purchase here.
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Why this works:
If it were up to us, we’d dress like Trinny Woodall every single day of our lives. Her style epitomizes Feminine Tomboy on every level, from the comfy white sneaks to the sparkly oversized blazer. Her balance of smart and casual, statement and subdued is always utter perfection, and while we sadly have yet to be invited to any occasion that commands a full-on sequined blazer, we love the nod to something sparkly and feminine in this otherwise completely laid-back look.
How to recreate it:
We swapped out the blazer for THIS sequined camisole for an understated effect. Pair it with THIS stretchy blazer, so the twinkle peaks through.
For a cropped, straight-leg jean that looks wildly good on any size thighs, hips, butt, or waist, we highly recommend THIS style from the most classic (and proven) of denim brands.
And no one will ever be allowed to say anything lame about the fashionability of THESE heavenly cushioned New Balance sneakers after they’ve seen them worn with this outfit.
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Why this works:
Whether you opt for a tucked button-down or a boxy tee , the concept of toning down such a classic Katharine Hepburn look with looser layers and a sneaker just makes sense. It’s a look that replaces jeans and a t-shirt that works for the weekend, the office, or out at night. And it’s less boring than 87% of the things you would have been wearing.
How to recreate it:
In addition to being the best possible drapey trousers to wear with any Feminine Tomboy look, THESE drapey trousers are the best ones we’ve ever worn with anything. Period.
Same goes for THIS button-down. We’ve called it out as the best the minute we tried it on. And we stand by it today. But if you prefer. a drapey tee to a button-down (and really we all could use one anyway), THIS one is our favorite.
With a look that’s more minimalist such as this, we like to add a more interesting or expensive bag. The details of THIS woven messenger bag from Clare V. make it nothing short of a work of art.
And, naturally, this is another place to let THOSE NB sneaks shine.
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Why this works:
This one is a bit of a fusion of many of the things you’ve seen thus far. And isn’t that the point? Being able to mix and match in ways that always leave you looking exactly how you always wish you would. A belted wide-leg pant with a spacious tee or turtleneck is another way to create glorious proportions and to make our comfiest boyish clothes look styled and expensive.
How to recreate it:
Start with the pants. The fabric on THIS pair is belly-melting, bump-smoothing, stretchy magic.
Tuck in THIS same sweater or THIS tee we spoke of earlier.
Cinch it with THIS menswear-inspired J. Crew belt, and slip on THESE same Doc Martens to balance out the boxiness you have going on up top.
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At The Candidly, we try a lot of stuff so you don’t have to. We only recommend things we truly love, and that we think you’ll love, too. All products are chosen independently by our creative team, and all details reflect the price and availability of products at the time of publication. If you buy something we link to, The Candidly may earn a commission.
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