4 tips to transition a woman’s wardrobe from professional to retirement


Pamela Lutrell shopping Chico's for wardrobe transition from professional to new life-style

Today, I would like to discuss four tips to transition a woman’s wardrobe from professional to retirement… with confidence.

I want to thank reader Kate for commenting about her feelings now that she is in this transition to a retirement wardrobe.

Kate, I know you are not the only one to feel lost in the process.

Pamela Lutrell shops Chico's for her new life-style transition

Chico’s Striped Tunic

Though I am not fully retired, I am in a new place where I can be more relaxed and creative with my style. That is why I have been in dressing rooms often lately…experiencing different looks in order to discover what my new confident life-style will be.  You can see there are hits and misses.

Pamela Lutrell shops JJill for transition to new life-style away from professional world

So, these are the tips most important for me to keep in mind during this time:

  1. I want to wear clothing that makes me smile when I look in the mirror and portray confidence.  If I put on something that drags my attitude and confidence down…then it needs to go! A sloppy sweatshirt, or dirty tee with ill-fitting jeans, needs to go.  For some reason, I am liking me in some of the hoodies I have tried.  Like the Soft Elements from JJill here…however, I have not purchased a hoodie as of yet!  You can also see that this Pure Jill Brushed Scoop neck (below) at JJill is a cute, flattering option to a sloppy oversized sweatshirt.  There are ways to step up casual.  When I was a mother of young children, I let go of me and looked sloppy more days than not. That must not happen during retirement or semi-retirement. 

Pamela Lutrell shops JJill for nicer casual style in wardrobe transition to retirement

2. What do I want to tell the world about me with my style through this transition? It always matters what you say with your style whether it is to a boss or client….or a neighbor or a grandchild.  My style is part of the legacy I leave. What I wear tells others something about me…no matter what shape it is in.

Therefore, I create my Pamela-style by communicating consistent, daily messages about me.  

I personally do this by selecting five adjectives and making sure each outfit I wear communicates those five adjectives. For years, I have referred to this as my Foundational Five. If what I am wearing does not say these five things to me, then I change.  Since I left the professional office world, I have been tweaking my adjectives, but currently I have decided the list will be







Pamela Lutrell shopping in Chico's jacket kept through wardrobe transition out of professional world

I have used my adjectives as I “purge” my professional wardrobe…and I recently did another purge…that is three since leaving the professional office world.  However, there are pieces from that life I have decided to hold on to, such as this gold Chico’s jacket (it communicates my adjectives).  I have written often how much I love a blazer with jeans…that is a foundation look for my style. I also use the adjectives for shopping and transitioning the wardrobe.  I do not want to purchase something that does not speak to who I am in this transition. 

The adjectives help me to be confident in my skin.  Any woman can possess confident style… no matter your income level, your age, or your size.   Just decide what you want to say about you and hold to it every day!  Don’t allow the “frumpys” or the “lazys” to take over in the transition.

Wardrobe transition ideas at Chicos from professional to retired life

 DRESS for each day as if it holds something special….because it does.  When I leave the house now, I step up my game just a bit.  Of course, there are days we weed the garden or clean out closets.  But don’t let those tasks dictate your style overall.

  1. I can be comfy, cozy, relaxed and wear a confident smile.  How?  Well, fit is always critically important even with casual clothing.  I can’t be confident in ill-fitting clothes.  Clean clothes are absolutely an attitude changer…I must resist temptation to grab yesterday’s outfit and wear it again today.
  2. I have to be ME and true to my own adjectives. Sometimes comparisons to women on blogs or especially on Instagram can be self-defeating and demoralizing.  Get to a point where they can be inspiration, but not self-defeat.  Daily dressing is between you, your mirror, and your adjectives. 

 How will you portray confidence and say what you want to say during this new time of life?  We are the only ones who know our lifestyle and what we are doing and dealing with every day.  Our reader, Shirley, will now be caring from grands…when I care for grands, I look nice in order to inspire them, but wear clothing that will survive popsicle stains and mud!!  One more thing: Workout clothing is great and so stylish these days…make sure your recreational clothing instills confidence. I do feel very confident going to the grocery in a cute workout look with fun sneakers.

Pamela Lutrell in Joan Oloff sneakers for new life-style transition from professional world

These are the key points on my mind during a life-style transition these days, but if you have specific questions, then please ask and I hope these thoughts will help.

Tomorrow, I am going to show you how I have kept some elegance in my wardrobe and, also, show you a friend’s wedding/casual chic style.

Below is a slideshow of stylish “stepped-up” casual styles for any woman…..



Remember, no matter what you are wearing during your transition time, make sure you can always


By Pamela Lutrell


  1. Thank you for this post. I am transitioning as well from full time work to retirement and I have realized I have tons of ‘work clothes’ and need some more casual pieces, but do not want to look sloppy. You have some wonderful suggestions today and I appreciate them as well as many of your readers probably share this as well. I am purging more than just my wardrobe as we are in the process of moving from our current home into another that was left to me due to my Mother’s passing. Her house is paid for, ours is not so we made the obvious choice. Thanks again for sharing your insight on transitioning into a retirement wardrobe.

  2. I always enjoy your try-on features. That Chico’s blazer is a beauty! These are good tips for transitioning to new phases of life, no matter what they may be. I also tweaked my Foundational Five adjectives too, and was surprised at how they have changed. This is due in part to finally feeling comfortable being retired (this took a long time), and also to steering away from my habit of purchasing office wear. I’m still drawn to it even after several years. Those adjectives are so helpful in both dressing for our days and in shopping!

    1. I have always been glad that you have seen the results of the five adjectives, Karen. It does make a difference and they do need to transition as our lifestyle transitions. Thanks for the support!

  3. Hi Pam! Love the JJill hoodie you were modeling! That is the look I am looking for in my upcoming retirement/”Mimi daycare” days to come! Comfy, practical yet stylish! Even though I have almost 3 months before I fully retire (I LOVE that word! 🙂 – I have already started my “purge”. I had a load of clothes and shoes and a few purses in the back of my SUV and drove one little town over to donate them to a local church who has a “Clothes Closet” ministry for folks in need. It felt so good to know that these clothes – even though I no longer wanted or needed them – were still in good shape and that would be a blessing to someone who could really put them to good use. Even though money will be tighter, I find that my needs are becoming smaller. Just being home, finally able to focus on those things I planned to do “When I Retire” – as well as spending time with my Little Loves (thanks for the mention! So excited to be able to help my kids with some daycare when needed – not to mention all the fun and snuggles I’ll be giving and getting!!!! ) When so many are fearful and anxious today, my heart is full of hope and love and faith in my Jesus! Be blessed today!

  4. Thank you for your post. I love jjill and find the sizes so reliable. Due to covid I’m “saving” my good clothes for when we can travel and socialize again. My problem was gaining weight over the past 9 months and it’s not with child! Somehow I lost 25 pounds before quarantining and it most of it magically found me when my only activity was grocery shopping and cooking. 😩

    1. I hear you, Janet. You are certainly not alone. A challenge of COVID has been to MOVE every day and keep it going. Even if you just walk around the house…that is better than sitting…or cooking. My cooking is going to turn uber healthy now that the holidays are past.

  5. My paternal grandmother was a manager/trainer for Max Factor many years before women were much in the workforce. She was so classic, chic and elegant, she still looked like she was going to work many years into retirement. She was a huge influence on my style and taste, but times are way more comfortable now. I need to find an adjective to replace “polished” now that I’m retired, because it’s causing me to veer right back to work looks, an easy mistake for me to make after so many years of spending the vast majority of my clothes budget for workwear. I’m debating putting in “active” but am wondering if that implies constant athleisure?

    1. What about “engaged”? Meaning that you look engaged, current, active in the life you are leading currently. I can see where polished might trip you up in the casual area. Maybe some of the readers have an idea as well…if I think of another, I will chime back in.

      1. I retired early ( at 51) and I’m 71 now. In these 20 years I still haven’t come up with a look I feel comfortable with… so much depends on my weight. When thin, my casual is jeans ( always straight leg for length)with tucked in blouses or t’s and a cool belt and a short leather jacket. When I’m pudgy like now, it’s yoga pants( still straight legs) with a hide it all fleece on top. I will NOT accept the pudge and buy bigger clothes. I don’t have the $ and I will never get to my healthy weight that way. So I’m going to search my closet for some clothes that speak to this transition: chubby to thin, as well as long ago retired professional.

        1. Try selecting adjectives with what you want to say with your outfit and then go into your closet and put together looks that say about you what you want others to say…that keeps you confident during the weight ups and downs.

  6. While I don’t plan on retiring for several years, I think that business dressing has certainly become more casual, especially during the past year when everything seemed to become more relaxed. I enjoy dressing fashionably but I’ve always placed comfort high on the list.

    Unfortunately I’ve gained weight over the past year and am having a hard time losing it. Some of my clothing is no longer comfortable so when I do shop, I try to find items that will work if I lose or gain weight.

    Many of the pieces you’ve shown would really work for me now! This is helpful.

  7. That blue/white chicos came in the mail today, can’t wait to take it out for a spin. I’m loving in retirement, the time I have to get ready to go somewhere, no rush, I can try on outfits and if something isn’t right anymore, I have a donation basket right in the closet and in it goes. I’m trying to teach myself new shopping habits, that’s harder for me…

    1. Don’t beat yourself up, Sheryl. From listening to others, this is difficult for most. Learning how to adjust a wardrobe to this new phase of life takes time…give yourself permission to take the time.

  8. I have been retired for almost 11 years, & I am still tweaking my wardrobe. At first, I fell into the trap of wearing things because they were good enough to wear around the house but would never wear them when leaving home. In the past few years, I have come to the realization that it is ok to look nice for myself. This was & continues to be a big step for me. In fact, I wore a blouse this week that made me feel drab, so once it is laundered, it will go into the donation bag.

  9. Oh, man. I loved working & I love retirement, but this wardrobe transition business challenges me. I did the opposite from many, as I’ve mentioned before: because my work clothes were casual — jeans, a shirt or sweatshirt with a tee under it, hard-hat & work boots — when I retired I thought I’d wear all the “cute” clothing I’d missed out on for 35 years.

    Turns out I like my jeans & tees & they suit both my personality & lifestyle. Even my husband is happier: “for a while there I felt like I was cheating on my wife” is how he put it. “you weren’t you.” 🙂 I’m back to being me & my challenge now is staying in the casual lane but putting a more fashionable twist on it. And I’m STILL working on my 5 Adjectives: Confident, Bold, Smart, Sassy, Competent.

    And speaking of jeans & a blazer: I was watching a couple of videos of VP-elect Kamala Harris & just love her look, slim jeans, a blazer, a simple tee & her Converse sneakers. She radiates such joy & confidence. So much about how we present ourselves is in the attitude, not the clothing itself. I’ve found that watching YouTube videos of woman whose style I admire is a real education.

    1. I like your adjectives, Janet. I find myself living in jeans more and more these days! Thanks so much for being here.

  10. Loved this blog. I have been retired for many years now. The major change in clothes came when my husband died and with him an active social life with lots of travel. Of course with the virus that is out of the question for all of us. Now a clean pair of jeans and a tee shirt seem to be what I wear most of the time. I do always wear earrings and keep my short hair trimmed in an effort not to look like a sheep dog. I do like your positive attitude and great suggestions. Thank you.

    1. You are welcome, Jill. A clean pair of jeans, a tee and great hair is a excellent way to face the day!!

  11. Great article! As a retired nurse after 32 years, I was accustomed to wearing scrubs for most of those years. I wore scrubs and had a few nice outfits for church and going out and that is it. I am now fully retired and involved with a few charities, church and going out. I realized some time ago that I tend to dress slouchy and that is what originally brought me to your blogs. I have been transitioning to improving myself and trying to dress with elegance. style, and confidence. Your blogs have helped me so much. Thank you. I also want to let you and your readers know that I ordered two shirts from Foxcroft and I was amazed at the fit, the packing, and the promptness of the service I received!

  12. Love, love this post! I retired 2+ years ago, and although I have purged a good bit of my work-drobe, I still need the wisdom of you and your readers to set me in a new direction. This got me thinking more about what’s left in my closet and how to make it current for my new lifestyle.

  13. This post struck a note with me today.
    For me the last 2 years since retirement has been a major transition. Determining a ‘style ‘ in my retirement life is taking longer than I expected. Your comments and strategies will be my focus for the next while. I’ve chosen one adjective- curious!

    1. Curious is a great adjective, Karen! I believe you are the first…that I am aware of…in the audience to select it. May we all be curious in life!

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