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How To Dress Your Age (It's Not What You Think)

While we're more inclined to define life stages by our own set of milestones (signing your first lease, buying your first investment piece, getting that promotion), age is an undeniable fact of being human. Many a life lesson comes to pass as you move from decade to decade, and with time your identity and your wardrobe both start to crystallize. To help guide you toward a more cohesive closet, we've gathered 30 style all-stars that will act as outfit building blocks for years to come. Solving your quarter-life crisis, however? That's all you.
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For a lot of people, the 20s is a decade of firsts: your first job, your first serious relationship, your first time living on your own. So, your wardrobe should reflect this exploratory time and be built on play-hard pieces that can keep up with your constantly evolving, fast-and-furious style. You’re trying on different fashion personas now, so malleable pieces that work wherever your adventures may take you are key. You may not always feel confident at this stage of your life, but your closet essentials certainly are fearless.
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20s: The Wear-Everywhere Dress
An easy throw-on-and-go dress really does go the distance in a twentysomething’s arsenal. Having a blank canvas that can take you from an awkward family wedding to brunch with your maybe S.O. and back again is worth spending a little bit more than that impulse buy when it’ll get this much wear.
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20s: Show-Stopping Earrings
A pair of multi-stone earrings brings even the most basic look together for those mornings when you can’t think about wearing anything but black skinnies and a crewneck.
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20s: Sky-High Platforms
You’re constantly on your feet at this age, so you need kicks that will elevate your style, but also give you support (so you can avoid those podiatrist bills in your 30s — truth). That’s where wedges come in. Go for a pair in shiny metallic to keep ‘em fancy for your jam-packed iCal. Extra cred if you splurge for a pair by Terry de Havilland, the go-to cobbler of never-not-partying Kate Moss as well as many iconic British It Girls from the 1970s.
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20s: Put-Together PJs
It’s time to put away the college tee and team sweats. You’re a grown-up now and, along with paying taxes and not crying at the dentist, that means wearing matching pajamas.
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20s: The Concert-Ready Crossbody
You don’t want to lug a big tote everywhere. A crossbody (in detailed leather) keeps your hands free to juggle drinks at the Banks concert or to carry shopping bags on a Saturday afternoon of perusing boutiques with your main crew.
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Now that you know how you see yourself fitting into the world, your 30s is the time to go and make your dreams a reality. And, persistence is your M.O., not just in your career, but also your wardrobe. Yep, you go that extra mile. Raise by raise, you’re slowly accumulating the items you’ve always wanted to own that together will serve as the cornerstone of your style. While you’re still fine-tuning your everyday uniform, investing in classic items you’ll literally have for the rest of your life (assuming you’ll take care of them) really can be money well spent.
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30s: The Forever Watch
It’s okay to spend a little (okay, a lot) of cash on the single accessory you’ll actually wear every day, forever. Plus nothing says “I mean business” like a watch that would make a CEO jealous.
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30s: Ladder-Climbing Blazer
A crisp, double-breasted jacket feels more modern than single-breasted option and will cinch in around your waist in a flattering way.
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30s: The Investment Commuter Bag
Leave your canvas tote and hobo bag at the door. Now’s the time to invest in the one satchel that will carry your laptop, iPad, heels, and everything else while adding polish to your look.
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30s: The Fit-You-Like-A-Glove Jeans
There’s a reason designer jeans cost what they do. If you choose the right pair (dark-wash skinny jeans are the most universally flattering), you’ll come across sophisticated and not too casual. Plus, your butt will look amazing, just saying.
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30s: Signature Specs
There’s no reason to wear contacts all the time, especially with glasses this cool. You’ll look impossibly smart and professional in a pair of slightly oversized, tortoiseshell specs.
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30s: The Good Hair Day Necessity
You've got your signature hairstyle down, but you don't really have the time to style it just so. This multi-purpose foam protects against heat damage, decreases drying time, and eliminates frizz. Bam!
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You’ve come to the age where you are very in tune with who you are. And, after enough trial and error in career, personal life, and (most noticeably) style, you know who you definitely aren’t. You’re comfortable in your own skin (at last!), so let your wardrobe convey that confidence. Now’s the time to perfect your very own sartorial mix, which means doubling down on the things you love that truly make you, well, you.
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40s: THAT Jacket
The moto, parka, and denim jackets are already hanging in your closet. So, it’s finally time to splurge on that eye-catching showstopper that just makes your outfit.
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40s: Luxe Lingerie
What's underneath should feel just as considered as what you're showing to the world. And, that starts with pretty lingerie that's as elegant as you are.
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40s: The Weekend Uniform
You’ve done the jeans and knit thing for decades. Give your Sunday uniform a sophisticated upgrade by opting for a jumpsuit. It’s what all the French women are wearing, after all.
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40s: Everyday Jewelry
By now, your jewelry box is filled with special trinkets from travels, relationships, and treating yourself to stuff you like. A pounded-metal cuff makes a nice addition because of its wear-with-everything brass finish.
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40s: The Black Tie T-Shirt Dress
At this point, you have one or several black shift dresses, so now’s the moment to mix it up with something a bit more unexpected that’s incredibly sexy in its simplicity. Plus, how rad would it be if you showed up at a gala in the fanciest t-shirt ever?
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40s: The Perfect Shade Of Red
Who doesn't look good in crimson lipstick? No one, that's who. Splurge for this beauty in deep wine.
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You no longer need to prove just what you’re all about, which means you've got the head space to indulge in life’s major upsides (like using those vacation days, for once). Add pieces to your closet that really help you live your life better, rather than get in the way of the adventure of it all.
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50s: The Sleek Raincoat
Just because it’s raining, doesn’t mean your jacket game should suffer — that windbreaker you’ve had since 30 won’t do anymore. A classic silhouette with an updated twist (note the see-through detail) is quirky, yet sophisticated.
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50s: Globe-Trotting Luggage
You’ve worked long and hard to be able to travel to that dreamed-of far-off destination. Functional luggage that won’t fall apart will ensure you get from home across the globe and back in a snap.
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50s: Denim Du Jour
It’s okay to have a little fun with your wardrobe — and that boils down to your denim. Hand-painted jeans that are one-of-a-kind tell the world you’ve still got it.
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50s: The City Boot
When looking polished is just as important as staying comfy, a chunky ankle boot, featuring fresh-feeling ponyhair, is your go-to for dashing around town.
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50s: A Perfectly Tailored Shirt
A button-up in classic blue is no-frills and gets you through everything, and custom alterations mean the fit will be impeccable. This specific option features a faint tuxedo detail that looks professional with a wink when tucked into trousers for work. It can also be worn undone with jeans when you’re running around town with the family.
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50s: Gorgeous Cream Blush
When you don't want to overthink your beauty routine, cream blush is a lady's best friend.
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You live by your own rules and no one can tell you what to do. So, why give in to fashion conventions now? Throw out the rule book for growing older gracefully and do what you please, while always turning to your favorite silhouettes. Mix your well-loved classics with on-a-whim buys that show you still know how to mix high and low, luxury and indie finds like the best of ‘em.
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60s: Conversation-Starting Necklace
A bold necklace is a no-brainer choice for a woman who likes her accessories to be as independent as she is, and this one from Lizzie Fortunato can keep up with your stocked calendar; it goes great with cocktail dresses and jeans.
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60s: The Rock 'n' Roll Suit
You’re about as chic as they come now, just like the Saint Laurent Le Smoking suit.
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60s: The Cooler-Than-You Shoes
Entering your seventh decade is no time for sartorial surrender. On the contrary! Metallic, colorblocked clogs are easy, sleek, and still give off that carefree vibe that you’re all about right now.
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60s: The Statement Scarf
A statement-making scarf is great for any age, but a tie-dye pick feels unexpected in a cool, downtown way.
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60s: The You-Earned-It Wallet
Splurge a bit on the little things, like a fancy wallet that’ll put your frayed, black coin purse you’ve used for 20 years to shame.
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60s: The Natural Shine
Silver for the win! This eco-friendly conditioner will help your locks look gorgeous, never yellow or dull.

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