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

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