New Life For A Favorite Black Jacket?

casual outfit with black jacket

I’m still just beginning to get a sense of how my style will transition as I shift from a full-time administrative position to being self-employed. At first, I thought I might want to go in a more Bohemian direction, but when I tried those styles, they just didn’t feel like me. I still want to look modern, polished and put-together, though not too stiff or formal.

Wearing: earrings (similar) | jacket (similar) | top | watch |
bracelet (similar) | bracelet | bag | jeans (similar)| shoes

I’ve begun going through some of my workwear pieces to see if they can Adapt To Life On The Outside. This lightweight wool black jacket has been in my wardrobe for a couple of years, and was always a favorite. I thought I’d see if I could style it for a more off-duty look, and I think it has possibilities. I might wear a look like this to meet friends for a casual lunch, or go to the movies or a museum. So I’ll hang onto the jacket a bit longer and see if I actually continue to wear it.

leopard top, Givenchy bag

Do you have any workwear pieces that you’ve successfully incorporated into your off-duty style?

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  1. I found that my NYC work clothes were hopelessly formal in small-town south of France–for the weather, culture, color, lifestyle. I donated a lot of clothes (and shoes) to a shelter for battered women, figuring they would need them for job interviews. Rolling up sleeves on blazers, as you do here, helps. Mixing formal pieces with very informal ones helps, but sometimes it just doesn’t work–it’s like whipped cream on a pepperoni pizza–two things that are each great but not at the same time. I also lowered the heels on my shoes. I used to wear loafers or ballerinas to work and change into heels that I kept in a desk drawer. Now I have to walk all the time in the shoes I’m wearing, no changing possible. So flats it is.

  2. I’ve bounced around, from the full-time work world, to free-lance here and there, to full-time stay at home mom. It’s true that shoes, for me at least, are the big divider. My ranks of higher heels I kept donating and thinning out. I loved them when they were appropriate, but now I like to move fast and be comfortable. Then foot surgery accelerated the process! So flats and boots (mostly) for me too. I have a couple of higher pairs for church and other occasions that call for them.

    I’m a skirt-wearer in even my most casual moments, but the type of skirts i wear now is different. Far fewer fine wool slim skirts, and far more “rustic” cotton and twill, with casual touches like pockets…

    I wear the same kind of shirts as before, basically. Button downs are versatile and subject to tweaking, and I usually wear with rolled sleeves and much of the same jewelry as before. I never wore strictly tailored jackets, so my collection of more relaxed jackets can move back and forth.

  3. I donated most of my dressier tops, skirts and dresses to an organization that helps women prepare for jobs. I am a plus-sized woman and the group told me that they really appreciated getting nice quality working clothes for larger women. I did keep a set of lightweight wool separates – black blazer, sheath dress, pencil skirt and trousers – that have served me well in retirement. Of those pieces, the blazer has gotten the most wear; so much so that I’ll have to replace it soon. It is a perfect topper that goes with almost everything else in my closet from simple dresses to jeans.

  4. I have pared down my closet considerably over the last three years. The most dramatic change I made was choosing to eliminate some random pieces. In addition to the basic black skirts and slacks I had accumulated several random colors: purple slacks and shoes…light tan slacks….green slacks. It seemed they mostly went with just one other piece, and so I eliminated those rogue items. Some didn’t have anything to “go with” anyway. Now my wardrobe is smaller but better organized, and definitely more casual. I did keep some jackets to spruce up jeans. And I’ve added a pair of colorful tights to go under a basic navy shift I used to wear with heels.

  5. It’s good to know that I’m not the only woman with this dilemma. I retired over 3 years ago from nearly 4 decades in corporate life and I’m just finishing clearing out the corporate suits from my closets. I traveled the globe in those clothes and many pieces had sentimental value. Donating them to Dressed For Success made me feel better about the process.

    Yup, shoes were and still are a big issue. I still wanna buy those black heels. I’m also working through training my eyes away from the black and navy suits. It’s what I bought for so many years.

    I, too, tried the boho look but just didn’t like it on my petite frame. Stevie Nicks carried it off 40 year ago and that’s where it should have ended. I think – but I’m still not sure – that a soft tailored look is for me. The sea of black in my closet also has to change – that might take some time.

    Please keep the transition blog and comments going. It is interesting to hear how others are handling this major transition!

  6. I think I have the only transition that was to a slightly dressier look! I worked for decades in the flavor industry and wore ‘sensible shoes’ to cushion the hard concrete and tile floors, non skid, thank you very much. I had a knee length lab coat worn daily , so my actual clothing was a conglomeration of wash and wear tailored pants ( poly rayon for that ‘wool’ look) and tops with stretch- light sweaters and knit tops and blouses. I would keep a neutral blazer on the back of the office door and that would usually be black. In case of a meeting, that would have to do . But in reality , the ‘suits’ would really enjoy seeing us tech folks dressed like tech folk. I think they believed if we were too dolled up, we must not be very good at our jobs!
    Now I wear mostly trousers and ankle pants with fun little booties and cute shoes. Tops that may not stretch ( woven blouses ) have crept into the closet. Some bedazzling on trim even.. LOL. Most of those wash and wear pants were donated. This part of my life has made shopping fun again.

  7. I kept a few blazers but only wear them with tee shirts, never other tops. Yours is a great jacket, and I’d love to see it styled with jeans, a white tee and either booties and very casual flats.

  8. I work in accounting in a small, albeit university town, where everything is casual dress. I rely heavily on Eileen Fisher for my work clothes so that I can can be well dressed but not over dress my clients. I wear clean lines with no frou frou which seems to be a good middle ground.

  9. I love all these comments, as I’m in the same boat. And I’m in a certificate program for apparel design. My focus is on designing for the “une femme” women, and myself, who is wanting to look relevant and great, but comfortable. As our bodies change and our style needs change, it’s important to look for well fit clothes no matter what styles. Fun times!

  10. Leopard and red! Love that. And my retirement style has taken its cue, as others say, from shoes. Sneakers, Birkenstocks, and more sneakers. Good thing they are in style now. All else has followed. I now find I am looking to up my t-shirts, jeans and jacket game, because that’s all I want to wear.

  11. Like so many of the comments above, I’m still transitioning from 38 years in a corporate setting to retirement. (I still have my St. John suits from the ’90s in my cedar closet waiting for a day that will never come!). I’ve been inspired by you, Sue, to focus on Eileen Fisher, especially long vests and sweaters instead of blazers. I just returned from a weekend in New York and felt comfortable and chic in some variation of my basics from daytime to the theater. Comfy shoes are a must but there are so many stylish choices I don’t feel there’s any sacrifice.

  12. I love reading all of these comments! It’s so hard to find a stylish, elegant, yet comfortable way of dressing for all of the occasions of life. Even when one is self-employed, there is a need to find the right way to develop the wardrobe. There are so many events and occasions to dress for, outside of work time. I like the idea of retaining things, like the blazer, and learning new ways to use them with other pieces. I would LOVE for this blog (Susan) to develop a style challenge or wardrobe challenge that is similar to others that have been started! I think you’d be great at this and would love to see what you could put together to help people put together a stylish wardrobe, such as yours, complete with accessories, shoes, bags, etc… Would you consider the challenge??? 🙂

  13. Let me add, that I know there are many “wardrobe challenge” blogs out there, but many are catered to women in the 30’s – 40’s age group, and I’d love to see someone take that same style savvy and apply it to fashions to recommend for a capsule wardrobe (seasonally) for women in the 50’s and beyond group. I am in my 50’s and thoroughly enjoy reading your blog!!

    1. That’s a very intriguing idea! Let me research a little bit and think about how it might be formatted, but I think it could be fun and a great learning experience.

      1. Just more info regarding the above comments…the blog has a tab for other stylists and bloggers with info about Stylegistix which is a tool for putting together and posting theses types if style challenges. I believe several other bloggers are using the same format to create their capsule wardrobes. Just thought I’d pass that along if you’re interested. There may be other optiond, as well!! Hope that helps!!

  14. I really like this outfit, especially with the punch of the shoes. The jacket is classic so I bet you find all kinds of new ways to style it. If you were feeling a bohemian vibe I wouldn’t be surprised if you slowly head that way but transitions are usually a long process. No matter what, I’m glad you are free to experiment and define your own boundaries now.

  15. Although I’ve been retired for a few years, I can’t bear to give away really nice business suits and dresses. This year I’ve been working at bringing a few jackets, skirts and dresses into my day to day wardrobe. A red suit skirt was my biggest success. So I set myself a challenge in the spring and brought out a few business jackets and wore them with jeans. I had fun but it seems to work in the cooler/colder months as summer is all about shorts and cut offs, beach and flowery dresses, none of which was my business wear!
    So, thank you, Susan, I’ve found some reasons to be cheerful as the autumn leaves fall, more jeans and jacket experimentation!

  16. I work corp during the week and literally can’t stand those clothes on the weekends, but a blazer like yours would be so great to throw over a pair of jeans and a cute top. I feel like it would make the outfit the perfect balance between too casual and too business. I am, once again, inspired by your blog and am going to add a black blazer to my wardrobe.

  17. I love that jacket on you. It is a classic style & a great length. I am currently reassessing my wardrobe now that I am retired. I have started to wear more tailored pants with a denim jacket & sneakers to dress the pants down a bit. I am quite happy with the look which means that I still get to wear some of my favourite pants. Thanks for highlighting this issue.

  18. Thanks again Susan for the ‘fashion challenges in retirement’ ideas. I retired four years ago and have become a minimalist wardrobe aficionado…sort of. It is joyful to see all my clothes on one rack with nothing from my past professional life. Everything in my closet is what I want to wear…nothing I have to make work. I’ve staged my walk-in closet like a boutique (thanks YouTube) and now love the freedom I have space-wise and fashion-wise. It’s fun to get dressed for the day now. My work is all volunteer and I too love Eileen Fisher! Some of the shoes & bags you show are out of my price range and I appreciate that you give us alternatives. You have wonderful style. Blessings…

  19. All you transitioning ladies, please please consider donating your corporate workwear to your local Dress for Success affiliate! I am a volunteer there and we always need donations, especially plus sizes. Anyone looking for a volunteer opportunity should also check us out. I will admit that one reason I chose to volunteer there was that it gave me a reason to still wear some of my professional business clothing I didn’t want to part with!

  20. And…please don’t forget us working girls! I am still about 5 years from retirement–At least! and work in a business where business casual means closed toe shoes and no denim. We still need your inspiration for the office/classroom/meeting setting. Thank you!

  21. Hang onto that jacket, Sue. It looks great with jeans. I’ve been retired for three years, and it was an e-mail ad for Net-a-porter called “Sunday Style” that inspired me with my “transition from work to play” wardrobe. So,like you, I’ve been dressing down all my professional wear.And if it doesn’t work for the new me, I’ve consigned it or sold it or given it away. Had a lovely afternoon tea party with several young colleagues my size who were thrilled to go home with suits and dress pants. That was the most fun! Every once in a while they send me a picture of them in their new duds.

  22. Wonderful post!
    Colette’s wardrobe architect is a wonderful tool for analyzing and developing your personal style. I hope you find it as useful as I did.

  23. I love the leopard print top, Susan, especially like the longer length and wondered if you purchased it in a regular or petite size?