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How to Look Classic, Not Stuffy

Elevate a traditional style with a few modern tweaks


spinner image Chico’s Wide Leg Linen Pants; Talbots Denim Button-Front Shirt in Marin Wash; LifeStride Women’s Kimmie Espadrille Wedges in Fire Red; H&M Women’s Pleated Skirt in Light Beige
(Left to right) Chico’s Wide Leg Linen Pants; Talbots Denim Button-Front Shirt in Marin Wash; LifeStride Women’s Kimmie Espadrille Wedges in Fire Red; H&M Women’s Pleated Skirt in Light Beige
Sarah Rogers (Source: Chico's; Talbots; LifeStride; H&M)

Many people prefer clothes that whisper “classy” to trendy ones that shout “Look at me!” In search of a pulled-together wardrobe with continuity, they steer clear of prints, bold colors and of-the-minute styles. This tasteful strategy is appealing until the “safe” clothes they depend on start looking dated. That’s a hint to get out of your fashion rut. The idea of a wardrobe that lasts forever is a fashion myth. Even if your weight stays stable, a classic wardrobe still benefits from a yearly reboot to keep a modern aesthetic going. Here’s how to jump out of the past and into the present with a cocktail of revised classics that are shaken and stirred.

spinner image Chico’s Wide Leg Linen Pants
Chico’s Wide Leg Linen Pants in Alabaster
Courtesy Chico's

1. Relax your core tailored pieces.

Tailored blazers, straight-leg pants, pleated skirts, button-down shirts and shirtdresses are still the basis for a classic wardrobe. However, they do change, and more styles are incorporating comfier stretch fabrics and knits, roomier proportions and updated details that push classics from cliche to chic. Your closet doesn’t need an entire makeover. Just one jacket, pant or skirt can launch an upgrade. Consider a stretch knit blazer like the Scoop Women’s Relaxed Scuba Knit Blazer in Racing Red or Whisper White ($45, walmart.com) or a knit “lady” jacket like the Mango Women Knitted Buttoned Jacket in Black ($80, mango.com), pants and skirts with a relaxed fit and elastic waistband like the Chico’s Wide Leg Linen Pants in Alabaster ($99, chicos.com, pictured above) and the A-line and midi length EP Modern by Evan-Picone Women’s Mid Rise Pleated Skirt in Black ($32, jcpenney.com) for instant oomph.

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spinner image H&M Women Pleated Skirt in Light Beige
H&M Women Pleated Skirt in Light Beige
Courtesy H&M

2. Mix categories to spice up outfits.

Most women over 50 know that adding a blazer to jeans and a T-shirt dresses up the casual twosome and dresses down the structured jacket. Still, many women still keep their serious work/tailored/going-out clothes pretty much separate from sporty/weekend items when pulling together outfits. That’s a mistake. One quick way to take the stuffiness out of classic clothes is with unexpected mixes that blur the lines. You may, for example, pair a chambray shirt or striped boatneck tee like the Free Assembly Women’s Boatneck Tee with Long Sleeves in Azalea Mitten Stripe ($13, walmart.com) with tailored pants like the J.Crew Factory Linen-Cotton Blend Elastic-Back Sailor Pant in Dusty Ivory or Black ($54, factory.jcrew.com), belt a sporty utility jacket like the Gap Women Belted Shirt Jacket in Chino Beige ($55, gap.com) over a pleated skirt like the H&M Women Pleated Skirt in Light Beige or Black ($46, www2.hm.com/en_us, pictured above) and add low slingback pumps and a fancy blouse to your favorite straight-leg jeans. The effect produces a cool I-just-threw-this-together vibe.

spinner image Talbot Denim Button-Front Shirt in Marin Wash
Talbot Denim Button-Front Shirt in Marin Wash ($90, talbots.com)
Courtesy Talbots
spinner image Goodfellow & Co Men’s Long Sleeve Collared Button-Down Shirt in Navy Blue
Goodfellow & Co Men’s Long Sleeve Collared Button-Down Shirt in Navy Blue ($30, target.com)
Courtesy Goodfellow

3. Style your clothes like a pro.

There’s a difference between wearing classics clothes and wearing them with panache. DIY styling tricks can quickly deflate the stuffiness and add a playful personal touch. For starters, resist perfection and a constant cycle of ironing, steaming and straightening the life out of your clothes. Stop buttoning every button and aiming for a fresh-from-the-dry-cleaner effect. A subtle lived-in look adds charm and attitude to classics. Start by unbuttoning a row of buttons to a V neckline, untucking or half-tucking shirts, roll longing sleeves … and do it a little unevenly — not symmetrical cuffs! Try swapping a polished leather belt for the self-tie belt on shirt dresses and layer a basic white tank under open shirts, jackets and cardigans for a contemporary combo. Guys can try toning tees to shirts or pants for a stylish monochromatic look and swapping old traditional shirts with long shirttails for the new shorter button-downs designed to be worn untucked. Or get all your favorite old shirts shortened to “untuck” level at your local tailor, as my husband did recently!

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spinner image Boden Women's Julia Jersey Shirtdress in Navy
Boden Women Julia Jersey Shirtdress in Navy
Courtesy Boden

4. Choose a new “go everywhere” dress.  

The little black dress (aka the LBD) worked for the era of pantyhose, shape wear, heels and full makeup, but today’s version of a classic “go everywhere” dress requires more versatility. It needs to look good with ballet flats, sandals, mules, boots and sneakers, have the flexibility to slip under a cardigan, get you through a day of work, errands or appointments and go to dinner or a weekend get-together without missing a beat. For maximum wear, make the dress black, another neutral color or a neutral print. Classic wrap dresses and shirtdress styles in new knits and midi lengths like the DVF for Target Women’s Long Sleeve Midi Sea Spots Black Wrap Dress ($50, target.com), the Loft Belted Pocket Midi Shirtdress in Perfect Camel or Black ($60, loft.com) and the Boden Women Julia Jersey Shirtdress in Navy ($77, bodenusa.com, pictured above) have 24/7 chops and built in comfort. And yes, below the knee midi lengths are now “classic” and a real asset for those hesitant to go bare-legged.

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spinner image LifeStride Women’s Kimmie Espadrille Wedges in Fire Red
LifeStride Women’s Kimmie Espadrille Wedges in Fire Red ($52, kohls.com)
Courtesy LifeStride

5. Let color, prints and textures wake up your closet.

The truth is, neutral colors like black, navy, white, beige, tan and gray really do give clothes a posh look. But a diet of solid neutrals can be boring to wear, and even the most tasteful clothes love a little sizzle. Shake up your closet by adding prints, stripes and textured fabrics like linen, pique, eyelet or crinkle gauze, or add one pop of color in your favorite hue of the minute — from bright red to pink or dusty blue — to any neutral outfit.

spinner image Naomi Watts at The Vineyard Theatre 40th Anniversary 2023 Gala honoring Billy Crudup in New York City
Naomi Watts
Bruce Glikas/Getty Images

6. Change your hair, makeup and sunglasses.

Whether you opt for styling tricks and fresh mixes or buy a few updates, don’t ignore what’s going on from the neck up! This may be the moment to cut your hair and recharge your makeup. Two archetypical classics — bobs and red lipstick — now rank as superpower solutions. Aside from the flattering visual benefits, a bob works for any hair texture but when blunt cut makes thin, fine hair look thicker. Red lipstick, on the other hand, restores color, definition and a dressed look to your face, even without any other makeup. Try a neutral classic red like the L’Oréal Color Riche Original Satin Lipstick in Maison Marais ($11, ulta.com) and the Revlon Super Lustrous Lipstick in Love That Red ($11, cvs.com) to get hooked for life. Finally, invest in bold black sunglasses with a hint of sex appeal like the swanky-looking WMP Eyewear Full Flat Lens Cateye Sunglasses for Women in Black frame/Gradient black lenses ($39, target.com). Who says you can’t be classic and a little trendy?

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