One of the great things about getting older is knowing what works for you—and what doesn’t. I’ve spent years refining my style, and while I don’t believe in chasing too many trends, I do believe in making thoughtful upgrades that help me look and feel my best. Adding a touch of a trend that aligns with my style keeps me looking and feeling up-to-date. Certain pieces in my wardrobe have seen better days, and others just don’t fit my lifestyle anymore. I’ve found that upgrading a few key items makes a big difference in how polished and put-together I feel. If you’re looking to refresh your closet, these are the seven pieces I think are worth upgrading in your wardrobe after 60.
7 Pieces You Should Upgrade in Your Closet After 60
I love brands like Cuyana, DeMellier, and Longchamp for their understated elegance and quality craftsmanship. A well-made bag lasts for years, and I like knowing that I won’t have to replace it season after season. If you prefer a crossbody for ease, opt for one with an adjustable strap that sits comfortably at your hip. The goal is to find a handbag that elevates your look rather than competing with it.
2. Tailored Trousers
The older I get, the more I appreciate a great-fitting pair of pants. I’ve owned plenty of trousers that were either too baggy, too stiff, or just didn’t sit right at my waist. Now, I’ve learned to look for pants with a smooth waistband that doesn’t dig in, a little stretch for comfort, and a silhouette that flatters without being too trendy.
A straight-leg or slightly tapered cut is my go-to. They skim the body in a way that feels effortless but polished. I love Eileen Fisher for her pull-on styles that drape beautifully. If you’re on the hunt for more great-fitting pants, I’ve rounded up my favorites here!
3. A Cashmere Sweater
SIMILAR HAT /SHOULDER BAG
There was a time when I thought any sweater would do. But after years of dealing with pilling knits and itchy fabrics, I’ve realized that cashmere is worth every penny. A great cashmere sweater feels indulgent, but it also elevates my everyday outfits in a way that nothing else does. The best part? With proper care, a great cashmere sweater lasts for years. My favorite cashmere sweater of all time is this Jenni Kane Fisherman sweater, which I’ve been lucky enough to find on sale during the Black Friday sales.
4. A Modern Blazer
I’ve always loved a good blazer, but as styles have evolved, I’ve realized some of my old favorites don’t quite work anymore. A stiff, boxy blazer can feel too corporate, while something overly fitted can feel a little dated. This sweatshirt blazer is a new favorite for its laid-back vibe and casual structure.
Now, I reach for blazers with a relaxed but structured fit—something that adds polish without feeling too formal. A slightly unstructured wool blazer or a soft ponte knit gives me the sharpness I want without feeling stiff.
Lately, I’ve been loving styles from J.Crew, Talbots, and Nic + Zoe. They have that effortless, modern feel while still being classic. I tend to stick with neutrals like navy and camel, but I also love a subtle plaid or tweed. I am a huge fan of knit blazers and woven jackets with stretch.
5. Stylish Flats with Support
/ ZIPPERED TOTE BAG
I used to think I had to choose between comfort and style when it came to shoes. But I’ve learned that the right pair of flats can do both. My days of flimsy ballet flats with no support are long gone, and I’ve swapped them for shoes that look chic but still feel great after hours on my feet. I’m a big fan of fabric shoes with stretch like these Rothy’s, which are machine washable.
A slightly pointed or almond toe elongates the leg without being too trendy, and I look for soft leather or suede that molds to my foot. I’ve found some wonderful options from Sarah Flint, M.Gemi, and Rothy’s that offer support while still looking polished.
6. Elevated Denim
Jeans are still a wardrobe essential for me, but I no longer settle for styles that are stiff, or uncomfortable. I look for premium denim with a flattering rise, just enough stretch, and a leg shape that works with my shoes. You can read more on my thoughts on current jean trends here. BTW, great denim can be found at many price points when you pay attention to fabric content. These Itty Bitty Bootcut jeans have an amazing fit and look great.
A high-rise or mid-rise straight-leg jeans is a classic choice that flatters most body types. Brands like AG, NYDJ, and Madewell make excellent options that blend comfort with style. A deep indigo wash or a rich medium blue feels polished, while a white or ivory pair is a great option for spring and summer.
7. A Timeless White Shirt
A crisp white shirt is one of those wardrobe staples that never goes out of style—but finding the right one makes all the difference. If your button-downs are stiff, boxy, or prone to gaping, it’s time for an upgrade. This Talbots no-iron shirt has been a favorite in my wardrobe for many years.
I also like slightly stretchy, wrinkle-resistant fabric that drapes beautifully without feeling stiff. Frank & Eileen, Eileen Fisher, and Banana Republic make elevated versions that fit well and hold their shape. A well-cut white shirt pairs effortlessly with everything from jeans to dress trousers, instantly elevating any outfit. Struggling to style your white shirt? Head over to this post where I share ten ways to wear this wardrobe staple.
What pieces in your wardrobe have you upgraded after age 60? Would you add any items to this list?