How To Dress When You’re Retired So You Don’t Look Frumpy

If you’ve recently retired, you may find yourself unsure about how to dress. On the one hand, it’s great to be able to dress down in comfy clothes, but on the other hand, it’s all too easy to let yourself go and slide into frumpville. Here are my top tips to help you find the happy medium in your retirement style.

1. Evaluate Your New Lifestyle

Wearing the right clothes for the occasion is a big part of looking stylish. Think about it. If you’re dressed for what you’re doing, you’ll feel good and always look appropriate. Before you buy any new clothes for your retirement lifestyle, give some long, hard thought to what that lifestyle will look like.

Do you plan to attend the gym for yoga or aerobics classes every day? Good for you! Stay motivated in pretty fitness clothes. Are you planning to travel? Ensure you have walking shoes that are both comfortable and cut. And if you’re looking forward to days of reading books, taking walks, and enjoying coffee with friends, look for pieces like jeans, leggings, cardigans, and boots that’re comfortable and easy to put on, yet still look stylish.

2. Embrace Comfort, Not Frumpiness

Gone are the days of pantyhose and heels. One of the benefits of being retired is that you can spend each day in comfortable, casual clothes. But just remember that ‘comfortable’ can still look good. Sure, wearing sweatpants around the house is easy and feels comfortable, but if you do this day in and day out, not only will you feel frumpy, but you’ll also feel embarrassed when someone drops by unexpectedly.

A better and equally comfortable option is a pair of leggings and a tunic top. When selecting leggings, opt for good-quality ones that are slightly thicker or faux leather leggings. Not only do they give you good coverage and help hold you in a little better, but they’ll also last longer. For a tunic top or sweater , opt for something that covers your bottom and is modern and current.

And don’t forget about footwear. Leggings look great in colder weather paired with riding boots or booties. In the spring and summer, opt for a practical yet on-trend pair of slip-on sneakers.

3. Don’t Ditch Cute Shoes and Accessories

Accessories truly make the outfit, and a great way to save money and look fab every day is to wear your core basics over and over again but shake them up in different ways with accessories. Change your necklace, add a scarf, and try a belt… The combinations are almost endless, and there are accessories for every budget. My best suggestion is don’t scrimp on your handbag. Not only do you carry it all the time, but it can also make a stylish statement, so look for a good-quality one.

4. Repurpose Your Work Wardrobe

If your former work environment was on the formal side, there’s a good chance you’ll have a suit or two (or five) in your closet that you paid good money for and can’t bring yourself to let go of. The good news is that you don’t have to. Repurpose a sit by breaking it up and wearing it more casually.

Take a look at what I’ve done in the picture above. I’ve taken a black leather Chanel style jacket and dressy blouse that may have had have in your work wardrobe and have paired it with a pair of jeans and a casual shoe. This would make a fabulous outfit for going out to dinner with friends, attending a lecture, or running out to see a movie. Keep the look polished by adding accessories and a rocking  small fun bag.

5. Don’t Let Go Of Grooming

Whether you’re working or not, truly stylish women over 40 understand that staying well-groomed is the key to looking youthful, regardless of what you wear. Things like maintaining a flattering haircut, giving yourself (or treating yourself to) a manicure, investing time in skincare, and wearing a little makeup can add up to make a significant difference in your appearance.

6. Have A Go-To Dress-Up Look

Even though most retirement lifestyles are casual, you will need a dress that you can count on for occasions like special dinners out and other events that call for slightly dressier attire. I recommend investing in a go-to dress that can be easily dressed up or down for a versatile look. Look for something flattering and not overly trendy, such as the pretty peach one I’ve shown here.

This is a timeless silhouette with a belt that provides a nice yet effortless definition at the waist. It’s also available in black, but I’m showing it here in the peach version, a shade that gives a nice flush of color to an over-40 gal’s complexion. If possible, opt for an item that can be worn year-round, paired with tights and boots or booties in the winter, and sandals like these comfortable nude ones in the summer.

7. Stay Up-To-Date With The Trends

Now, more than ever, it’s essential to stay up-to-date with the trends. Why? Because retirement means you’re less likely to be out and about and interacting with younger people. That means you’ll have fewer opportunities to see what people are wearing now, making it all too easy to get out of touch and begin dressing too old for your age. One effective way to stay up-to-date with the latest in real-life fashion and style is by visiting sites like Instagram and Pinterest.

Have you recently retired? How are you finding it? What do you typically wear?

Meet the author

Deborah Boland

Deborah, a former Fashion & Lifestyle TV host and Image Consultant, understands the style challenges women face in their 40s, 50s, and 60s. As the founder of Fabulous After 40, she helps women tweak their chic and embrace fashion with confidence—so they always look and feel amazing.

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