Our Privacy/Cookie Policy contains detailed information about the types of cookies & related technology on our site, and some ways to opt out. By using the site, you agree to the uses of cookies and other technology as outlined in our Policy, and to our Terms of Use.


Are You Dressing Your Age?

In your 20’s: Now’s your time to experiment with trends and have some fun. Face it, ladies, you’ll never look better! Start small by incorporating a graphic tee that showcases your big personality. Pair with ripped jeans by day; fitted pencil skirt by night.

To buy: Old Navy, $15

If ever there was a decade to rock those towering heels you’ve been eyeing, now is the time. Try a wedge if you’re new to the rodeo, or go bold with a classic stiletto. Whatever you choose, be sure to walk confidently - a teetering, unbalanced gait does not a stylish lady make.

To buy: Piperlime, $120

In your 30’s: By now, you’ve learned what works for your body and what doesn’t. And if you’ve added babies to the equation, your shape has likely changed a bit in the last decade. Fret not! A leather A-line skirt is both age-appropriate and universally flattering, but youthful in texture. Pair with that graphic tee you were sporting 10 years ago for a more grown-up version of the same old, lovely you.

To buy: H&M, $35

Whether you’re climbing the corporate ladder, saving lives or changing diapers, your 30’s are a perfect time to take yourself a bit more seriously. Don’t want to reinvent your entire wardrobe? Just add a blazer. Whether sporting your favorite boyfriend jeans or a fitted wrap dress, a tailored blazer adds class to any look. Throw in a jeweled statement necklace to keep things light, rather than stuffy.

To buy: Topshop, $90

In your 40’s: Feeling frumpy at 40? Meet your new best friend: the tailor. Whether you’re less-than-enthusiastic about your widening hips or are worrisome about a sagging bosom, tailors are magicians in disguise. Look for classic pieces in a quality fabric (we love these slimming pants!) and throw in a few extra bucks for a nip and tuck… no, not that kind!

To buy: J. Crew, $90

A great underwire bra is a must if your girls are feeling the weight of 40. Pro tip: your size might have changed drastically in the last decade, so be sure to visit your local boutique to be fitted for your proper dimensions. This everyday design boasts comfort, class and is - shall we say - uplifting? You’re welcome.

To buy: Target, $17

In your 50’s: Quality fabrics in a medium weight make all the difference in flattering your figure, so embrace nubby textures like twill and tweed in the winter; linen in the summer. One closet staple you’ll rely on time and time again? A classic white button-down. If it’s good enough for Diane Keaton, it’s good enough for you.

To buy: L.L. Bean, $40

Every wise woman knows the power of a great accessory, and at 50, meet yours: the scarf. Whether tied turban-style around your hair or looped on your neck, a chiffon scarf will add loads of personality to any wardrobe. For bonus points, try a bold, leopard pattern - YOLO, right?

To buy: J. Crew, $45

Don't worry; we haven't forgotten the bag! Here are four bonus options to tote around for decades to come...

In your 20's: Celebrate life's events - big and small - with this confetti-inspired clutch. Keys, phone, wallet, GO.

To buy: Lord and Taylor, $96

In your 30's: Forgo the overly floral, mega diaper bags in lieu of a stylish crossbody that you can sport long after the tots have grown.

To buy: Nordstrom, $295

In your 40's: You're in need of a multipurpose tote that will age as graciously as you do; this 100% Argentinian leather tote will do the trick nicely.

To buy: Cuyana, $150

In your 50's: Bold and unexpected, this forest haircalf mini bag doubles as a wallet for everyday use. Perfect for tucking in your signature red lipstick and those years of wisdom you've gleaned.

To buy: Loeffler Randall, $395

More from lifestyle