Javascript is not enabled.

Javascript must be enabled to use this site. Please enable Javascript in your browser and try again.

Skip to content
Content starts here
CLOSE ×

Search

Leaving AARP.org Website

You are now leaving AARP.org and going to a website that is not operated by AARP. A different privacy policy and terms of service will apply.

How to Look Classic, Not Stuffy

Elevate a traditional style with a few modern tweaks


Many people over 50 prefer classic quiet clothes to trendy ones that shout “new.” They avoid bold statements, loud colors and exaggerated details. This self-confident, no-gimmicks attitude is admirable … until it starts looking dated, dowdy and dumpy. That’s when a few stylish changes are a good idea. Here’s how to keep the classic aesthetic going but jump out of your time capsule and into a more contemporary version of yourself:

spinner image A New Day Women’s Boxy Long Sleeve T-Shirt in Black/White Striped; Maeve Plus The Denim Colette Wide-Leg Jeans in Denim Medium Blue; Quince 100% Organic Cotton Knit Blazer in Camel; Old Navy Oversized Striped Shirt for Women in Mini Blue Stripe
Left to right: A New Day Women’s Boxy Long Sleeve T-Shirt in Black/White Striped ($15, target.com); Maeve Plus The Denim Colette Wide-Leg Jeans in Denim Medium Blue ($130, anthropologie.com); Quince 100% Organic Cotton Knit Blazer in Camel ($70, onequince.com); Old Navy Oversized Striped Shirt for Women in Mini Blue Stripe ($28, old navy.gap.com)
Target; Anthropologie; Quince; Old Navy

1. Update core pieces

Classic blazers, striped tees, high-waist jeans and button-down shirts have blown up on social media. Take a closer look. That blazer may be a knit, the tee may have dropped shoulders, the jeans feature a wider leg and the shirt is oversized. All are still classic but with a contemporary twist that’s far from boring. There are very few “timeless” classics that last or look flattering forever. Stretch fabrics, relaxed fits and updated design details make all the difference.

spinner image Image Alt Attribute

AARP Membership

Join AARP for $12 for your first year when you sign up for Automatic Renewal. Get instant access to members-only products and hundreds of discounts, a free second membership, and a subscription to AARP The Magazine

Join Now

spinner image J. McLaughlin Women Cody Denim Jacket in White; Old Navy Rib-Knit Tank Top for Women in White Lilies; oft Chambray Oversized Everyday Shirt in Fresh Blue Wash; Talbot’s Field Jacket in Rattan; Superga Women’s 2750 Cotu Classic Sneaker in White
Clockwise from left: J. McLaughlin Women Cody Denim Jacket in White ($198, jmclaughlin.com); Old Navy Rib-Knit Tank Top for Women in White Lilies ($13, oldnavy.gap.com); Loft Chambray Oversized Everyday Shirt in Fresh Blue Wash ($49, loft.com); Talbot’s Field Jacket in Rattan ($120, talbots.com); Superga Women’s 2750 Cotu Classic Sneaker in White ($66, amazon.com)
J.McLaughlin; Old Navy; LOFT; Talbots; Amazon

2. Mix dressy and casual items

Just adding jeans to a dressy blouse or tailored jacket is a fast formula for flipping classics from conservative to cool. But don’t stop there. Try pairing tailored pants, skirts and dresses with a more casual jacket. A leather moto jacket or blazer is the obvious choice, but jean jackets and cargo/utility styles work well for warmer weather. Blend sporty hoodies, chambray shirts, white tanks and sneakers with your more structured or work-worthy pieces. The unexpected blend is the secret sauce that animates a classic recipe.

spinner image Bonobos Stretch Everyday Shirt in Grey End On End; Abercrombie & Fitch Nylon Trench Coat in Light Brown
Left to right: Bonobos Stretch Everyday Shirt in Grey End On End ($89, bonobos.com); Abercrombie & Fitch Nylon Trench Coat in Light Brown ($120, abercrombie.com)
Bonobos; Abercrombie & Fitch

3. Style your clothes

Styling tricks give button-downs, shirtdresses and belted items a casual lived-in effect and fast-track them from formal to fashionable. First, try wearing a shirt untucked and rolling up the buttoned sleeves. Don’t aim for perfection — the more uneven and rakish the better. Unbutton the necklines of prim and proper blouses and shirtdresses to a V-neck. Not only does it look fresher, but you’ll elongate your neck and torso. Guys can look for dress-casual shirts designed for untucking with a strategic mid-zipper length. And always tie and knot trench coat and shirtdress belts instead of buckling up.

spinner image Boden Women Rivera Collar Maxi Shirt Dress in Vermillion; H&M Women Jersey Wrap Dress in Cream/Zebra-print; Banana Republic Sedona Linen Dress in Buffalo Brown
Left to right: Boden Women Rivera Collar Maxi Shirt Dress in Vermillion ($144, bodenusa.com); H&M Women Jersey Wrap Dress in Cream/Zebra-print ($35, www2.hm.com/en_us/); Banana Republic Sedona Linen Dress in Buffalo Brown ($190, bananarepublic.gap.com)
Boden; H&M; Banana Republic

4. Choose a new “wear everywhere” dress

The “little black dress” is legendary for dress-up/dress-down situations. However, many LBDs that worked in the era of high heels, 9-to-5 corporate clothes and shape wear look dated today. Instead, try a below-the-knee midi in a wrap or A-line and shirtdress styles to fill the gap and wear with anything from a modern sneaker to sandals to flats. Though black always works, try a floral, animal print, a warmer neutral such as brown, tan or olive or even a classic red as an alternative. It’s the dress you’ll wear to run errands, work from home, wear to the office or out to dinner.

Entertainment

Ancestry

30% off a 1-year subscription

See more Entertainment offers >
spinner image Gap Linen-Cotton Blazer in Rose Crystal Pink; Rothy’s The Flat in Bright Red; Artisure Women’s Classic Leather Penny Loafer Drivers in Red; GH Bass Women’s Weejuns Whitney Exotic Penny Loafers in Emerald Croco
Clockwise from left: Gap Linen-Cotton Blazer in Rose Crystal Pink ($128, gap.com); Rothy’s The Flat in Bright Red ($129, rothys.com); Artisure Women’s Classic Leather Penny Loafer Drivers in Red ($41, amazon.com); GH Bass Women’s Weejuns Whitney Exotic Penny Loafers in Emerald Croco ($165, macys.com)
Gap; Rothy's; Amazon; Macy's

5. Add color to energize clothes

Neutrals such as black, navy, gray and beige are the backbone of a well-considered wardrobe, but a steady diet of them day after day can be boring. Classic fans often resist color, but all you need is one pop to give a spark to a basic look. The key is to stick with classic styles. Shoes are the simplest entry point, so try loafers, loafer mules or flats in a primary red or green. For an even bigger update, select one of your favorite and most-worn items of clothing — a blazer, cardigan or skirt — and try it in a color you love. Hint: makeup shades in pinks, corals and reds are always flattering.

spinner image Naomi Watts, Gabrielle Union and Sharon Stone
(Left to right) Naomi Watts, Gabrielle Union and Sharon Stone
Bruce Glikas/Getty Images; Matt Winkelmeyer/Getty Images; Marc Piasecki/FilmMagic

6. Tweak your hair, makeup and sunglasses

Bobs are back, red lipstick looks brand new, and aviators could not be hotter. These are all classics reinvented for 2023 that can amplify your style efforts and are worth another try. (FYI: A “box” bob is the trendy new name for a classic, blunt, chin-length bob — which is still one of the ultimate “fatteners” for thin, fine hair.) All variations of the bob from wavy to shaggy to textured are super-chic. Red lipstick comes in a vast array of shapes and containers from the classic bullet to chubby pencils, tinted balms and liquid lips in a tube with a sponge applicator. Choose a texture and red hue that resonates for you from sheer to full strength. Finally, invest in an updated pair of aviator sunglasses with angular or oversize teardrop frames. Who says you can’t be classic and trendy?

Discover AARP Members Only Access

Join AARP to Continue

Already a Member?