7 Pieces You Should Upgrade in Your Wardrobe After 60
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
1. Your Everyday Handbag
A well-chosen handbag pulls an outfit together, and after 60, it’s time to move beyond trendy bags that lack structure or sophistication. If your current go-to is showing wear, feeling too heavy, or looking a little outdated, an upgrade is in order. I look for a mid-sized leather bag with clean lines, minimal hardware, and a shape that transcends time. I want something that looks polished but isn’t fussy. This Toteme T-Lock bag switches from clutch to shoulder bag with ease.
I also carry a tote more days than not and find a beautiful leather tote elevates every outfit. My current favorite tote is my small zip-top leather from Cuyana, which I share more about here.
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!
I keep black and navy on rotation, but lately, I’ve been adding lighter neutrals like taupe and ivory to freshen things up. They pair beautifully with everything from sweaters to structured jackets.
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.
I typically gravitate toward a classic crewneck or V-neck in a neutral tone, but I also love a great cardigan and turtleneck. The key is finding one that’s lightweight enough to layer but substantial enough to feel luxurious. I’ve found wonderful options at all sorts of retailers, with the most budget-friendly selection is at Quince. Looking for more of my favorite cashmere? Check out my full list of recommendations (and my tips for caring for your cashmere) here.
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.
Loafers have also become a staple in my wardrobe. They give just enough structure to make an outfit feel intentional, but they’re easy to slip on and go. If you need more arch support, Vionic and Birdies are great brands that blend comfort with style.
P.S. I’ve rounded up even more great options in The Best Comfortable Loafers and Flats for Women Over 50.
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?
Subscribe to A Well Styled Life
Click here to sign up for my email newsletter and get first access to all my blog posts and more sent straight to your inbox.
I appreciate your blog and read it often. The issue I have with white shirts is that for I can’t wear stark white. I would also like some stretch. What would you recommend?
There are lots of soft and off white shirts available. Check J Jill
Hi, Jennifer…
As usual, a very very helpful post. One request, though. When possible, please note the rise in pants and jeans. I am short-waisted but have a torso that is very long overall. I have tried so many wonderful looking pants – Athleta Endless Pants, Quince, Eileen Fisher, etc. But my body needs a 12-inch rise, and I seem to spend too much time returning pants. I’m thinking of hiring a tailor to sew bespoke pants so my closet includes something more polished than jeans. BTW, Lands End is one of the few retailers that varies the rise length with size. All my LE jeans are Tall size 6 for the rise, hemmed by the tailor for my short legs! Thank you!
Not all brands label the rise but I will be sure to call it out when I can. I prefer a high rise also. Good to know about LE!
I loved the post today, very informative. I know it’s after the fact, but I realized there were a few things about dry eye that were not mentioned yesterday. Never ever sleep with a fan on in the bedroom (my husband knows this) yes, it dries your eyes out even when they are shut. Watch that the car vents are not blowing in your face, because they always are. Heat is generated by your computer, yawn and take lots of breaks. And I was told by an eye doctor years ago that the single most important thing you can do is drink plenty of water. ‘Plenty’ is twice as much as you think, so you want know where all the ladies rooms are. LOL
Lol, great points! My husband loves a fan on in the warmer months so I’m committed to sleeping in an eye mask.
Fantastic post thank you Jennifer. l just turned 61 and now l am far more interested in clothes that will last and are quality rather than fast fashion. I recently splurged on a Barbour Beadnell Sage jacket and l wore it nonstop abroad this winter and now back in the States. Love the Frame cashmere turtleneck you recommended too.
I’ve been eyeing the Barbour barn jackets but waiting for a color that appeals to me. Quality is so worth it! Better for the planet too.
Hi Jennifer
Great post that I will refer to time & time again in the future as I continually upgrade my wardrobe with thoughtful purchases . I don’t always do that and now I realize that I have a lot of clothes that are not the best for me. A lot of jackets with gold buttons for ex when silver is better for me.
Question – Do you buy the Organika Canadian made Marine Collagen Powder or the Vital Proteins Marine Collagen ? I thought it was the Vital Proteins which is the one that I purchase but maybe you have switched ?
Little details like buttons can make a big difference. I use the Vital Protein powder.
Thank you for sharing these tips. The image with the Birdies loafers looks elevated because of the scarf. A scarf instantly elevates most outfits, like a cashmere shawl in autumn and winter.
Thanks for the post today.
So enjoyed your tips.
I find Vivaia footwear offers more footbed support than Rothy but with the same fabrication and comfort. I also wanted to tell you wore my white jeans with chocolate boots and pink sweater out in the cold weather and loved the look.
It sounds like a fabulous outfit!!
I recently discovered your blog and enjoy the focus on our age group. I I live in California, am retired and do some form of exercise daily such as yoga, walking, gym, strength straining. I do these activities at various times of day depending on my schedule for the day. I would love to see a post on athleisure wear because that’s what I find myself wearing most days. I’m not crazy about the short tops that are in style now and would love to see some tunic and average length tops for different seasons. I’m average size at 5’5”.
Great post Jennifer. Always appreciate the things you find and share!
Can you tell me about the blouse you’re wearing with the Athleta navy pants in this post ? That outfit has such simple polish, great for the work place !
It’s a stretch blouse from J.Jill from a few years ago. It packed like a dream and never wrinkled.