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

If you’ve recently retired, you may find yourself at loose ends when it comes to deciding how to dress. On the one hand, it’s great to be able to dress down in comfy clothes, but on the flip side, it’s all too easy to let yourself go and slide into frump-Ville. 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 go to the gym for yoga or aerobic classes every day? Good for you! Stay motivated in pretty fitness clothes. Are you planning to travel? Make sure you have walking shoes that are as cute as they are comfortable. 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 are comfortable and easy to pull on but 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 good but if you do this day-in, day-out, not only will you feel frumpy, you’ll feel embarrassed when someone drops by unexpectedly.

A better and equally comfortable option is a pair of leggings and a tunic top. When it comes to selecting the leggings, choose good quality ones that are a little thicker. Not only do they give you good coverage and help hold you in a little better, but they’ll also last longer. As for a tunic top, choose something that will cover your bottom and is modern and current. The one I show here is in shades of purple and violet, the 2018 Pantone color of the year.

And don’t forget about footwear. Leggings look great in colder weather with riding boots or booties and in the spring and summer, opt for an on-trend yet practical pair of slip-on sneakers. I chose these in lavender, a Spring fashion trend color.

3. Don’t Ditch 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 really 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 letting go of. The good news is that you don’t have to. Repurpose a sit by breaking it up and wearing it more casually.

Look at what I’ve done in the picture above. I’ve taken a standard black blazer that you probably have in your wardrobe and have paired it with a pair of jeans and a casual shoe. This would make a fabulous outfit for going out to lunch with friends, attending a lecture, or running out to see a movie. Keep the look polished by adding accessories and a-rockin 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 secret to looking youthful no matter what you wear. Things like maintaining a flattering haircut, giving yourself (or treating yourself to) a manicure, putting some time into skincare, and wearing a little makeup add up to make a big difference in how you look.

6. Have A Go-To Dress-Up Look

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

This is a timeless silhouette with a belt that gives it a nice yet easy waist definition. 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 you can, choose something you can wear year-round, with tights and boots or booties in the winter and a sandal like these comfy nude ones in the summer.

7. Stay Up-To-Date With The Trends

Now, more than ever before, it’s important to make a point of staying up 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 good way to stay up on the latest in real-life fashion and style is by viewing 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.

Learn More About Deborah Explore Her Latest Posts