10 Ways To Dress Comfortably (But Chic) In Your 60s
Getting older doesn’t mean giving up on style, but it does mean adapting your wardrobe to better suit your changing body and lifestyle.
I’ve spent years helping women in their 60s find that sweet spot between comfort and chic.
Now I’m sharing my top tips for looking pulled-together without sacrificing an ounce of comfort.
These aren’t just fashion rules—they’re practical solutions for real women who want to feel good in their clothes.
1. Embrace Soft Knit Sets
Matching knit sets have completely transformed my wardrobe since turning 60. They offer the ease of a sweatsuit but look ten times more polished. The trick is finding sets with structure—think ribbed fabrics or subtle patterns that hold their shape.
I recently bought a camel-colored set with wide-leg pants and a boxy top that feels like pajamas but looks like I made an effort. The best part? No fussing with separate pieces in the morning.
Look for natural fibers like cotton blends that breathe well. Many brands now make these in gorgeous jewel tones and neutrals that mix and match beautifully with other pieces you already own.
2. Upgrade to Premium Stretchy Jeans
Gone are the days of uncomfortable denim digging into my waist. Premium stretchy jeans with a higher rise have been my game-changer. They smooth everything out while providing serious comfort.
The secret is the fabric technology—these aren’t your granddaughter’s jeggings. Modern stretch denim with at least 2% elastane gives you movement without bagging out at the knees by lunchtime. Straight or slightly bootcut styles balance proportions beautifully.
Pair them with a silky blouse or fine-gauge sweater for an instantly put-together look. Dark washes work hardest in any wardrobe, but don’t be afraid of medium washes with minimal distressing for a more casual vibe.
3. Master the Art of Layering Lightweight Pieces
Layering has saved me countless times when dealing with unpredictable temperatures. The key is using thin, lightweight fabrics that don’t add bulk. My go-to combination starts with a simple cotton tank or shell.
Over that, I add an open shirt, lightweight cardigan, or unstructured blazer. These layers create visual interest while giving me options throughout the day. I can add or remove pieces as needed without looking disheveled.
Stick with similar color families for a lengthening effect. I love navy with lighter blues or creams with tans. This approach keeps things coordinated even when you’re peeling off layers in an overheated restaurant or adding them back on in chilly theaters.
4. Find Your Perfect Midi Dress Formula
After years of trial and error, I’ve found midi dresses to be the most flattering length for women our age. They hit at that sweet spot between knee and ankle that’s universally flattering and appropriate for almost any occasion.
My formula is simple: slight A-line shape, elbow-length or 3/4 sleeves, and a fabric with a bit of drape. This combination skims over the areas many of us feel self-conscious about while highlighting our best features. Jersey knit is particularly forgiving.
The beauty of a great midi dress is its versatility. I wear mine with flat sandals for casual days, low block heels for dinners out, and even with stylish sneakers when I’m being a tourist. Add a denim jacket or lightweight cardigan to extend the wearability.
5. Swap Stiff Trousers for Elevated Joggers
Who knew joggers would become my wardrobe hero? Not the gym variety—I’m talking about the elevated kind made from flowy fabrics like Tencel, fine cotton, or silk blends. They’ve got all the comfort of sweatpants with none of the sloppiness.
The magic is in the details: look for pairs with flat front waistbands, subtle tapered legs, and refined finishes like cuffs or side stripes. I pair mine with structured tops to balance the relaxed bottom half—a crisp button-down or a fitted knit works beautifully.
For footwear, leather loafers or sleek sneakers keep the look intentional rather than like you forgot to change after your morning walk. These trousers work for everything from grocery shopping to casual dinners with friends.
6. Invest in Statement Comfort Shoes
Shoes can make or break comfort, especially as we age. I’ve finally stopped torturing myself with uncomfortable footwear and discovered brands making stylish shoes with actual support. My feet have never been happier!
The current trend toward chunky soles and practical designs has been a gift. Brands like Ecco, Clarks, and even Cole Haan have created options that don’t scream “orthopedic” but still offer cushioning and stability. Metallic finishes and interesting textures elevate basic styles.
I invested in three key pairs: a supportive sneaker in a neutral color, a cushioned loafer with a slight platform, and a block-heel sandal for dressier occasions. These cover all my needs while keeping my feet and back happy through long days.
7. Try Wide-Leg Pants with Fitted Tops
Wide-leg pants have become my secret weapon for comfort without sacrificing style. The generous cut through the leg gives me freedom of movement while creating a lovely flowing silhouette that’s both modern and flattering.
Balance is everything with this style. I always pair my wide-legs with something more fitted on top—a tucked-in tee, a slim-cut blouse, or a body-skimming sweater. This proportion play keeps the look from overwhelming my frame.
High-waisted styles work best, creating a long, lean line. I love them in linen for summer and wool blends for cooler months. The right length is crucial—they should just graze the top of your shoe to create that elegant, unbroken line from waist to floor.
8. Perfect the Art of Accessorizing Simply
My wardrobe became instantly more versatile when I mastered the art of simple accessories. Instead of trendy pieces that quickly look dated, I focus on quality items that add polish to even the most basic outfits.
A few well-chosen accessories work harder than a closet full of mediocre ones. My essentials include a medium-width leather belt, a couple of silk scarves in colors that complement my wardrobe, and statement earrings that frame my face nicely. These pieces transform simple basics into put-together looks.
I’ve learned that less is definitely more at our age. One standout piece—like a beautiful scarf or interesting necklace—makes more impact than piling on multiple items. This approach feels more modern and lets your natural elegance shine through.
9. Discover the Power of Thoughtful Layering Pieces
Lightweight jackets and toppers have revolutionized my wardrobe. Unlike heavy blazers or structured coats, these pieces add polish without weight or restriction. They’re perfect for our age when comfort is non-negotiable.
My collection includes an unlined linen blazer, a knit cardigan with subtle structure, and a kimono-style jacket that works over everything from jeans to dresses. The key is finding pieces with some drape that still maintain their shape. Avoid anything too boxy or oversized.
These third pieces instantly elevate simple outfits and solve the “arm coverage” issue many of us prefer as we age. They also provide that finished look that makes casual clothes appropriate for lunches, appointments, or shopping. Even better, they’re perfect for travel when temperatures fluctuate.
10. Embrace Forgiving Wrap Styles
Wrap dresses and tops have been my reliable friends through weight fluctuations and body changes. They adjust to your shape, highlight the waist (or create one where needed), and offer customizable coverage that’s so helpful as we age.
The V-neckline of most wrap styles is universally flattering, drawing the eye up to the face. I look for true wraps or faux-wrap styles that don’t gap or require constant adjustment. Jersey or similar knit fabrics offer the perfect combination of structure and give.
For cooler weather, I layer a thin turtleneck underneath or add a cropped cardigan on top. Prints work wonderfully in wrap styles—they add visual interest while being forgiving of any lumps or bumps. These pieces always earn compliments while feeling like secret pajamas.