Fashion Over 50: Retirement vs. Professional Dress

A reader recently asked me about the day I will retire…which I have no idea when that day will come.  She asked what I would keep in my wardrobe and what I would donate away?? The pictures in this post are a sampling of some clothing I have in a folder called, WORK WEAR.


The question had me thinking, so here is what I decided…

  1. I would probably own less skirts, and dresses.  Some are needed for special occasions, but not as many as I have for professional events.  I also feel more confident in pants these days.

2.  I would keep most of my jackets, toppers, cardigans etc.  One of my favorite pumped up casual looks is to wear jeans with a nice fitted jacket.  This is a perfect style for lunch with the girls or working at a non-profit.

3.  I would donate the suit pants…in retirement I see me in mostly jeans, knits, and leggings.  But I would keep one or two of my nicer dress pants for special occasions.  I want to be comfortable, but also confident and not sloppy.


4. I would keep ALL my accessories!! Just cannot imagine parting with them…and they could help me make retirement outfits more fun and Interesting!  However, I might donate some of my shoes….or, maybe not…they would be hard to say goodbye to!


5.  I would keep one long professional coat for special occasions, and donate the others.  This would leave me with my car coats, jackets, and wraps.

There are just not that many changes I would make except to have less, because there are fewer days I am before a professional group.  But, retirement to me is not an excuse to look sloppy, or tired, or frumpy.  I still want to look and feel confident with my wardrobe.

Would anyone like to add anything to the conversation about transitioning to retirement?





  1. Since I work in a professional office, kind of stilted, I am dressed up all of the time in dress pants with jackets, dresses, skirts with jackets, etc. I am definitely planning retirement and like you Pam, I would be donating some of my dress pants and dresses, but not all, keeping blazers and jackets for the most part, though a few would go. I see myself in retirement as working part time, doing something that is nowhere near an office!!, and I will need more casual things. Some shoes would go for sure, and I would let go of all but one long dress coat and all but one dressy car coat. Actually, I think I would probably be simplifying my casual wear to more of a J Jill casual kind of vibe, more knits. But as you said, I would never lean toward frumpy or sloppy. I really am looking forward to that closet purge!

  2. I turn 60 this year so even though I’ll retire sometime in the next ten years, I plan to still work outside the home in some way. I work in an office now and business casual is the attire, so I foresee keeping pretty much the same type of wardrobe … comfy and stylish pants, skirts and jackets (emphasis on comfy)!

    1. I hear you, Beth…comfy is key and it is so good that with today’s fashion options we can be comfortable and look great!

  3. As a retiree who recently moved across the country I have found that it really depends upon your lifestyle and location – just like work wear does! I would suggest that new retirees wait a whole year to see what you are doing and wearing before donating anything unless you absolutely dislike the garments or they are worn out. You may surprise yourself by what your new style becomes as your activities evolve.

  4. I love your list of “What you’d keep and what’d you’d let go” when you “ever” retire! I’m surprised you didn’t end with – check back with me in 10 years! If I was having as much fun as you seem to be having, I’d leave that whole retirement thing up in the air, too! 🙂 Seriously, I agree with your choices – less structure, more comfort – and still looking good doing it! My husband and I are so looking forward to the time we can “come home” as we call it! We have so many things we plan to do – travel, volunteering at our church/missions projects, spending as much time as possible with the grands! BTW – I LOVE your hair in #4 (keeping all your accessories)!!! That length is so very flattering! But of course, you always look fabulous! Thanks for such a great, informative blog! Stay warm!

    1. Thank you, Shirley! We look forward to the same list of activities! I know I will be working for awhile! And for now, that’s OK.

  5. When I retired, I was happy not to have to wear scrubs everyday and to roam around my home in comfy clothes. However, after following this blog and some others I realized that my transition into a different lifestyle which involved volunteer work, visiting, traveling, etc.; was all new to me. My identity was connected with my job–I was a nurse and when I retired I realized, I really did not know who I am. It has been an exciting journey as I have lost weight and experimented with different fashions and have found a wardrobe that seems to give me confidence as I learn to try new things and venture out into new areas. I am still on the journey of losing weight so most of my clothes are purchased through Thriftown, Clothes Mentor, and Goodwill. I aim for clothes that I can mix and match. I can dress jeans up or down. Blazers and sweaters are important items and can be worn even if weight goes down. Accessories are wonderful in changing the complete look of an outfit with a purse or jewelry. I now slip on makeup and nice outfit just to go to the grocery store not to impress others but to feel good about ME and a smiling me seems to be contagious with those I meet everyday. I also had to add some work out clothes to my wardrobe since I now exercise as part of my day. It is amazing what cute tops and bottoms they have these days! This blog has given me so many ideas of how to pull together my retirement wardrobe! Thank you so much Pamela!

    1. What an awesome comment, Teresa Ann. It sounds like your have gone from scrubs to fun! I so happy you have gained some inspiration here. Thanks for sharing.

  6. I retired 2 years ago and was very concerned about what I would wear ‘on the other side’. I found that I don’t wear my dresses or my many business jackets or my heels.

    The big change is that my jackets and topper sweaters are longer. Now that I wear pants, almost exclusively, I need something to cover my butt.

    I’m now enjoying wearing bracelets as I don’t have to worry about them getting in the way of writing or banging on a conference table. My pearls and scarves remain with me. It’s been fun! ?

  7. I was in a professional environment for the past 40 years and am now semi-retired doing contract work. Even if I’m in my office by myself, no appointments, lunches, etc. I need to feel “put together” for my own self-image. I did donate many, many suits and professional dresses but kept a few of everything. Also, some of those little black dresses are good to keep around. I donated lots of shoes and coats. I love having mostly one style in my closets and I also love buying new outfits that I would not have previously purchased, because I wouldn’t wear them to work. I kept all my accessories. Even a jacket and casual slacks or jeans begs for a scarf and cute flats. How I dress impacts how I feel in any environment/situation.

  8. I retired several years ago and moved to a 55+ active adult community and love this life style. My wardrobe now of course is more casual. My favorite style is jeans with white shirt and blazer. But I am having trouble finding jeans that look good on me. I carry my weight unfortunately In my legs, so can not wear skinny jeans and even straight leg jeans do not look good most of the time. I mostly wear the Chico traveler pants. So I have kept most of my blazers that I wore when working.

    Can you tell me what size shoe you wear. You have worn so many good looking flats and wonder if you wear a M or W. if you wear a W what brand do you find work the best for you.

    1. Hi Esther, You might try the jeans at dressbarn (now called Roz & Ali). They fit well and have all types of lengths and cuts for the legs. I wear a Medium shoe and my favorite lines are Rockport Total Motion and Sam Edelman. I hope that helps. Thanks for the comment.

  9. I always worked in the design and arts field and ran my own business…so it was “business casual” usually. Now I am running a business from my home, in a retirement community of sorts, but still dress every day. Black leggings, colorful top, always a scarf and jewelry and ballet flats. Yes, many fewer skirts or dresses except in summer when I prefer them anyway. I have many meetings, either for my business or my HOA board or Garden Club. Many people wear jeans and sneakers…but that was never me before so it certainly is not now! I think our personal style carries over as we age and transition into new ways!

    1. I think you are right, Libby…we do transition in new ways. I look forward to seeing how that works for me when I am ready.

  10. I retired 16 years ago and at first kept my suits and blazers, dressy coats and heels-just in case. I never wore a single one of them after I left work, and my lifestyle changed dramatically-I volunteer in a vegetable garden that donates produce to food banks, and also with other garden related organizations. I am constantly out of doors, running from project to project. Always in jeans and t shirts, frequently filthy! I love it! To each his own…when I do dress up, it is almost always in pants and a nice jacket, with booties or cute sneaks (not big white athletic shoes). An Hermes scarf and some nice earrings, and I can go anywhere I care to go. I like looking up to date during those times, but I don’t worry about fashion when I’m gardening.

    1. I can see me hanging on to things I may not wear and eventually pass along. Sometimes we just have to get into the new lifestyle to figure it out. The gardening sounds fun and so worthwhile!

  11. Retired 12 years ago. I got rid of my skirts and dresses, as I wear pants all the time. I find a lot of good pieces at Chico’s that work with my lifestyle. I periodically go through my fashion accessories and weed out the things I don’t wear anymore. I did not get rid of any of my shoes 🙂

  12. I have been retired for almost eight years. It took me a while, but I donated my power suits & most of my dresses & skirts to Dress for Success. My uniform of the day when I’m staying home is a simple top & comfy jeans or shorts, depending on the season. Yes, they have elastic waists but don’t judge. When I’m out & about, I wear dress jeans. I am partial to cardigans with sleeveless tops or sweaters in winter. In summer, I wear knee length skorts & well fitting t-shirts because I hate being hot. My shoes are a work in progress because I have really bad feet. I always wear makeup & do my hair even when I am staying home. I also always wear earrings at home & add other accessories when I am going out.

    1. Hi Becky…thanks for mentioning Dress for Success…a perfect place to donate professional clothing. I have the same “challenges” with heat so I understand. You might try Rockport shoes…they are so comfortable. Thanks for stopping by!

  13. I do plan on ditching the suits but otherwise I will wait and see. I won’t have the money to buy expensive pieces so I don’t want to get rid of things until I’m sure I don’t need them.I look forward to more freedom to wear my style and colour preferences and no matter what, I want to simplify!!

    1. Good comment about keeping your quality, investment pieces, Janet. If we need them, we have them and if not we can donate. Very good observation!

  14. This is an excellent choice of topic. I appreciate your post and all the comments that were shared. I agree that it will be a gradual change of wardrobe as I explore my transition into a different me. I’m excited to surprise myself.

  15. Pam – you look particularly stunning in the first photo in the fabulous blue jacket. Could you let me know where that jacket from? Thanks.

  16. We were obviously on the same wavelength today, Pam! My Fashion Friday post entitled “What do you wear at home?” dealt with my own transition from a working wardrobe to retirement. I’d love it if you’d stop by and let me know what you think.

    1. Good post, Elaine. You are so right that life is short…why spend that time sloppy and uninspired! Let’s dress like we are engaged and enjoying each day.

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