How to Stay Stylish in Retirement

Updated on December 22, 2019
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Freedom! You’ve retired, and can’t wait to give away, sell or recycle your work clothes. You no longer have to wear a suit and tie, or dresses, skirts, trousers and blouses.  But even though you may not need them anymore, those clothes were reliable and classy. It wasn’t hard to decide what to wear to work. What do you wear now that you’ve got time on your hands to pursue your interests or just relax? How do you stay stylish in retirement?

Who Are You and What Do You Do?

You may not be going to the office every day anymore, but you’ll be going somewhere – on a cruise, out to dinner, shopping around town, to the gym or just out to work in the yard. Think about how you’ll actually be spending your time and choose comfortable outfits that meet your needs. We’re not talking velour and terrycloth though. Choose quality fabrics, classic color combinations and pieces that are versatile and can be worn throughout the day and into the evening.


There’s nothing like the gleeful feeling of shoveling out an overstuffed closet. Many style experts recommend adherence to the “two-year rule:” if you haven’t worn it in two years, odds are you won’t wear it again. If it’s in good shape, donate or sell it. If it’s torn, stained or threadbare, your local recycling center may have a bin to chuck it into. If the item has sentimental value and you’re just not sure you can part with it yet, box it up and wait a year – if you still haven’t worn it, you’ll be ready to say goodbye.

Classics are Classic for a Reason

There are certain pieces that just never go out of style. A nice pair of black trousers and a classic white cotton shirt or silk blouse will always come in handy. A great pair of jeans that fit well, or leggings topped with tunics in quality fabrics and neutral colors can form the foundation of your new, more casual wardrobe.  Shoes can be comfortable without looking overtly “sensible.” 


It’s tempting to bust out those trendy looks you didn’t get a chance to wear because of work. But be attentive to the effect: express your personality but don’t try too hard.  Less is more with colors and prints as we age, and looser, more flowing clothing can be more flattering to a rounder silhouette than trussing up a softening body with too-tight clothes. Additionally, think twice about dyeing your hair.   Lean into your naturally occurring greys. Accepting yourself with confidence and expressing yourself with grace are the touchstones of how to stay stylish in retirement.

Accessorize Creatively

While your clothes may become subtler in color and looser in fit, retirement is when you can use accessories to make a style statement. Hats, bracelets, watches, bags, glasses and even canes can help you express yourself. A chunky necklace or bracelet, a dapper hat or a new, bolder eyeglass frame may be all you need. Don’t overdo it, though. Let a statement piece make its statement without interference from too many other add-ons. Remember, Coco Chanel once said, “before you leave the house, look in the mirror and take one thing off.” Then, get out there and enjoy retirement in style. 


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