How To Dress Your Age (& Which Buys Really Matter)

On one hand, we'd like to take age out of any equation in life and instead applaud milestones — landing that dream job, finding your life partner, traveling the world — regardless of when they're achieved. On the other hand, there’s a big difference between where you stand at age 25 vs. 45 — and between the many life lessons you learn at each age.

Just as your identity continues to evolve along your winding journey, so does your style. To help guide your fashion path as you climb that life ladder, we narrowed down 25 essentials to invest in, depending on your age bracket. We're talking foundation pieces to spring for in your 20s, plus the add-ons for all the subsequent decades. By all means, though: If you want to pick and choose fashions from every age, go for it. 

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Your 20s are an adventure — your time to discover who you are and who you want to become. As your sense of self evolves, so does your sense of style. You no longer need those labels you wore in high school to mimic your "cool" classmates. Now, you buy what you like — and, most importantly, what will keep up with your ever-changing life.
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20s: The Wear-All-Day Dress
A throw-on-and-go dress works wonders in a 20-year-old's wardrobe. If you had a late night out with friends, but still have to go to work the next morning, you can get an extra five minutes of snooze time with a frock that does the work for you. Because who wants to worry about putting together a semi-normal ensemble while still half-drunk?
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20s: The Perfect Black Booties
You're slowly growing your shoe collection, but you're not at the stage where you can (or want to) wear a different pair with each outfit. Invest in one style that goes with everything — your work dress, your going-out outfits, and everything in between.
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20s: The Multi-Functional Crossbody Bag
You're juggling a lot right now; keep your hands free with a stylish crossbody. Bonus points if you go for one that's not basic black.
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20s: The Going-To-Nail-The-Interview Suit
You're trying to land your first grown-up job right now, and you need the perfect suit to nab it. Choose a classic-feeling style that has a little personality to boot. Plus, you can easily mix and match these separates with other items in your wardrobe once you do get the job.
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20s: The Nice Pair Of Jeans
It's time to upgrade your denim collection, with a sophisticated pair that doesn't have too many bells and whistles (i.e., extreme whiskering and distressing). This one will work for casual Fridays and after-hours alike.
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You're kind of figuring it out by now. You may not be exactly where you want to be, but your job is better and your finances are a little more in line. And, your closet reflects that. Little by little, you can add in those classic, keep-forever pieces that define your personal style and show the world you mean business.
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30s: The Just-Because Heel
While you're not rolling in it, you may have some more extra cash than you did in your 20s. Splurge on that pair of heels you've had your eye on all season — just because you want them and deserve them. You work hard, girl.
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30s: The Screw Contacts Specs
You might have thought contacts were the way to go in your 20s, but after years of touching your eyes every morning, give it a rest. Plus, cool specs aren't the least bit nerdy.
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30s: The Power Bag
Show the world who's boss with a killer handbag that will be the envy of every one of your colleagues. Just make sure you go for a practical style that can actually fit your daily essentials.
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30s: The Forever Watch
This is the one accessory you actually will wear every day, so make it a good one. This silver-and-navy option is sophisticated, but still feels different from the rest.
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30s: The Everyday Earrings
It's no secret that the right pair of earrings can tie together an outfit. Spring for a cool pair that works with your entire wardrobe, but has some edge (you're still young!).
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You're on top of your game in most aspects of life. You get yourself, and you get your wardrobe. Confidence is key, and after (many) ups and downs in your 20s and 30s, you finally feel comfortable enough in your own skin to wear what you want. It's time to add those items that make you feel like your true self.
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40s: THE Coat
You've already got the staples — a trench, a denim jacket, etc. Splurge on a coat that will make you feel and look like a legend.
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40s: The Fancy Lingerie
Feel just as confident underneath your clothes, with a pretty lingerie set that's a major upgrade from the mismatched underwear you wore in your 20s and 30s.
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40s: The Black-Tie Dress
Stop trying to pass off your go-to cocktail dress as black-tie-appropriate. Go for a gorgeous gown for your next affair — one that will work for every formal function to come.
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40s: The Sleek Sneakers
Sneakers aren't just for kids. In fact, there's nothing cooler right now than a sophisticated woman wearing unexpected kicks with a more formal outfit.
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40s: The Updated Duffle
You've used that same weekender for years and years. Give your tattered style a rest in favor of something more elevated (but still practical) for your next business trip.
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You live by your own rules and let everyone know it. If you want to take a vacation, you do it. If you want to go out on the town, you go for it. Mix items into your wardrobe that will help you live your best life and make you feel happy (just like that much-needed, three-week-long trip to Bali).
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50s: The Perfect Blouse
It may seem silly to spend a lot on something as simple as a white blouse. But, it really is the most versatile piece in your wardrobe.
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50s: The It’s-Time Wallet
Swap out that wallet you've used for the last decade for a pretty, high-quality option that can double as a clutch for date night.
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50s: The Hide-Away Shades
You've got a busy life, and you wouldn't want it any other way. But, on the days you want to stay out of the spotlight, go for oversized shades with interesting details that highlight your personality.
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50s: The Upscale Trench
Everyone else is wearing a standard khaki trench; be the woman who stands out, with a graphic jacket that will actually make you excited when it rains.
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50s: The Party-All-Night Shoe
You're not the type to slow down, and you've got the funky (but sturdy) heels to prove it.
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By 60, you have a solid collection of classic staples. So, add in some offbeat, quirky pieces. Go all-out — or, just chill. Both are perfectly acceptable.
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60s: The Tailored (& Comfortable) Pants
Sit back and relax in non-skinny, non-constricting pants. That doesn't have to mean full-on sweats; soft, tailored trousers are cozy and still work for the office.
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60s: The Talk-Of-The-Table Necklace
You've mastered the art of hosting the perfect dinner party, so throw on an interesting necklace to spark conversation.
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60s: The Elegant Flats
You're never going to give up a good heel, but for the days when you do want to stay a bit more grounded, flats with fanciful details (like a high-shine metallic) have the same feeling as formal stilettos.
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60s: The Upgrade Sweater
Totally timeless. Switch it up with a cool knit to wear absolutely anywhere.
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60s: The Versatile Tunic
Throw this on over trousers, or wear it as a breezy dress for that last-minute vacay — or, you know, just for living your life.
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