Perfect Outfit Ideas For Every Age

They say age is just a number, but when it comes to your clothing, it’s also a fairly reliable indicator of what’s appropriate for you to wear. While we’re all for sartorial freedom of expression, it just feels wrong when someone who was around the first time Birkenstocks were cool is trying out trends fit for tweens.

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  • We’ve rounded up inspiring outfits and shopping suggestions for every age, whether you’re finding yourself in your twenties or balancing work and family in your forties or fabulous and fun in your sixties.

  • 20s: Experimentation

    Almost nothing is out of bounds (although office wear should show some restraint) so feel free to try out trends, reveal a little skin, and basically get down with your wardrobe in any creative or wild way you feel fit.

  • Denni Elias
    Photo credit: Style Du Monde

    Denni Elias, freelance creative consultant & blogger

    You’ve got one time in your life to wear hot-pants without earning serious side-eye, so if you feel comfortable, we say go for it! Just make sure to balance exposed gams with a covered-up top.

    Image courtesy of Style Du Monde

  • Laura Love
    Photo credit: Billy Farrell/

    Laura Love, model

    Alexa Chung has figured out how to pull off the schoolgirl shtick into her 30s, but for the rest us, your 20s are the ideal time to rock the nymphet look. Love nails the look by aligning her accessories, like a cheeky neck-tie and mary-jane heels, with the youthful vibe of the plaid babydoll dress.

  • Loeffler Randall Fenton Buckle Booties ($255) in Sand Leather

  • 30s: Sophisticated Trends

    By this decade, you’ve figured out your style and are hitting your stride in accomplishing goals personally and career-wise. Sure, you’ll still rock a statement sweater or wear a plunging v-neck, but you’ll do so with pieces that feel decidedly more elevated.

  • Eva Chen
    Photo credit: Kirstin Sinclair/FilmMagic

    Eva Chen, Editor-In-Chief of Lucky

    As a relatively youthful Editor-In-Chief, Chen balances trend-driven pieces such as her leopard sweatshirt with polished separates like a leather pencil skirt to create an image that is fashionable, yet powerful.

  • Taylor Tomasi-Hill
    Photo credit: Stockholm Street Style

    Taylor Tomasi-Hill, former Creative Director of Moda Operandi

    Notice how Tomasi-Hill finds sophisticated ways to show off her stylish side. Just check out how the playful pattern on her teardrop-print skirt is balanced by the office-appropriate hem-length.

    Image courtesy of Stockholm Street Style

  • 40s: Flexibility

    At this point, you’re less likely to chase every trend, and will be more focused on an intrepid mix of chic staples and statement pieces. Unfussy day-to-night options are key for a busy life that likely involves juggling family, career, and social life.

  • Jenna Lyons
    Photo credit: Leandro Justen/

    Jenna Lyons, President and Executive Creative Director of J.Crew

    Look to Lyons to see how a woman in her 40s can expertly navigate trends. A graphic popover shell makes a fashionable statement, but the overall effect is polished when paired with a basic button-down and trousers.

  • Nina Garcia
    Photo credit: IMAXtree

    Nina Garcia, Creative Director of Marie Claire

    Leather pieces are a great way to inject a little edge into your ensemble. Just make sure to choose pieces that aren’t skin-tight for an overall refined effect.

  • 50s: Wardrobe Workhorses

    Say yes to investment pieces that you know are worth it and will have for years to come. Forget those high-profile pieces that are uncomfortable and unpractical, instead opt for classic items that work as hard as you do.

  • Lisa Love, Senior West Coast Editor of Vogue

    Sheer sleeves are a genius way to show a little skin while still feeling somewhat covered-up.

  • Joanna Coles
    Photo credit: Taylor Hill/WireImage

    Joanna Coles, Editor-In-Chief of Cosmopolitan

    A boot cut pant is flattering to almost every figure, and the animal print feels like an age-appropriate way to inject a little oomph into your outfit.

  • 60s: Work Your Assets

    You’ve got a set style, and are likely well aware of which silhouettes are most flattering for your figure. Embrace that knowledge, and go ahead and treat yourself to that luxurious item that you’ve been thinking about for decades.

  • Tonne Goodman
    Photo credit: Style Du Monde

    Tonne Goodman, Fashion Director of Vogue

    Your closet classics can look just as sharp as any trendy item. Simply pair them with on-point accessories like a silk neckerchief and sunnies.

    Image courtesy of Style Du Monde

  • Anna Wintour
    Photo credit: Style Du Monde

    Anna Wintour, Editor-In-Chief of Vogue and Artistic Director of Conde Nast

    A sleeveless top puts the spotlight on Wintour’s arms—a wise move, considering they look incredibly toned!

    Image courtesy of Style Du Monde

  • Nicholas Kirkwood Pebbled Point-Toe Loafers ($395)

  • Michael Van Der Ham Printed Satin-Twill Skirt ($335)


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