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Monday Musings: Evolving Your Personal Style and What I Wore

I frequently receive questions about how to discover, refine, or evolve our personal style. While it’s tempting to think we can settle on a “formula” once and for all, that may not serve us well. Growing, learning, and changing are part of what makes life so engaging—and that includes how we dress. Our wardrobes should reflect who we are today, rather than being stuck in the past. This year, I’ll be diving deeper into ways to evolve your signature style, and I welcome any questions you may have.

My personal style is evolving this year because boredom set in last year, which is never a good thing. My closet clean out revealed I had too many duplicates in the same category and the sameness left me uninspired. Versatle pieces that make up the backbone of my wardrobe had taken center stage. Basics are critical but not at the expense of those unique pieces that give an outfit personality. In short, I had put myself and my personal style in a box which stiffled my creativity.

I prefer minimalistic color palettes and shapes, but they need to be styled with attention to the details that make them interesting. Here’s what I wore last week.

WINE RED SWEATER COAT SIZE M / SIMILAR NAVY WIDE WOVEN BELT / NAVY TANK TOP SIZE M / NAVY PONTE PANTS size S / LEGENDARY BROWS IN TAUPE / LIPSTICK IN SECRET SALMA / COLORSCIENCE IN CLASSIC

New Year’s Day- I worked from home because I had a slight stuffy nose and thought I had a head cold coming on. I knew I wouldn’t be leaving the house, but I never stay in my jammies…unless I have COVID. I put on a navy tank top and navy ponte straight pants from Loft, blue socks that sort of matched, and topped it with a wine-red knit sweater coat from Amazon.

The long sweater has no closure. I felt chilled and wanted it to stay closed, so I buckled on an old woven navy belt from Banana Republic. As always, I applied tinted sunscreen, which acts like a light foundation, and added tinted brow gel and plum-colored lipstick. If I skip brows and lips, my face looks pale and colorless, which would not help me feel better if I caught my reflection in the mirror. I liked the belt because it felt cozy for some strange reason and added a bit of structure to a knit outfit. I spent my day knitting, then worked on the blog a bit, and defrosted some of my husband’s homemade chicken soup for dinner. If the house had caught fire and I had to run out, I would have felt presentable, plus I was cozy and warm.

Last year, I would not have worn the wine red cardigan, and I certainly wouldn’t have bothered with the belt.

NAVY CROPPED SWEATSHIRT PEACOAT size S / CHAMBRAY SHIRT size M / DENIM SKIRT size 29 / LEOPARD PRINT BELT / KNIT SOCK BOOTIES / SHOULDER BAG / SIMILAR NECKLACE / MINI RESIN EARRINGS

Luckily, the cold never developed, so the following day, I met a girlfriend for coffee and an inspiring chat about fashion. Later, my husband and I went out to dinner with some other friends. It was not raining, but it felt clammy out, so I wore this cozy Sweatshirt Peacoat over a soft chambray shirt and denim skirt. I love a double-denim outfit and am always a fan of a column of color.

I accessorized with a bold link necklace (similar), stretch sock booties, opaque tights, and some new lucite earrings that my husband gave me for Christmas. Let’s be honest here: I ordered them, and he wrapped them up.

The outfit was feeling boring, so I swapped out my black belt for this leopard print belt because sometimes matchy-matchy feels uninspired. Before we left for dinner, I added a blue chiffon scarf with little pops of color on it because the neckline felt too bare.

SIMILAR TRENCH COAT / CHARCOAL WATERCOLOR BLOUSE size M / IVORY CARDIGAN size M / MOTHER OF PEARL EARRINGS / GRAY STRAIGHT LEG CORDS size 29 / SIMILAR BOOTIES / BLACK BELT

The following day, I met some girlfriends for coffee and a style chat at the mall. It was raining cats and dogs, so I wore my trench coat (similar) over this charcoal animal print blouse and ivory cardigan sweater. I accessorized with these Mother of pearl earrings, a black belt, and a necklace I’ve had for longer than I can remember, layered with a simple strand of pearls. Layered necklaces are making a comeback, and “charm” necklaces continue to be popular, so I strung an extra pearl onto the chain necklace. Black square-toe booties (similar) finished my look.

$50 CASHMERE SWEATER size M / STRAIGHT ANKLE LEG JEANS size 29 / SHOULDER BAG / MINI RESIN EARRINGS / SIMILAR SILK SCARF / BLACK VELVET FLATS / PEARL BRACELET save 15% with code AWSL

On Saturday, I headed out for a dressing room try-on, which you’ll see later this week. I wore. a simple black cashmere sweater, my AG Straight leg jeans, and black velvet birdie loafers. I carried my black Totême handbag and added a pop of color near my face with this blue scarf (from my wardrobe archives). Adding a flattering color near your face is a great way to soften the effects of black against your complexion.

The black shoes, bag, and sweater draw the eye up and down my body. I chose a blue scarf (similar) with soft greens to pick up the blue shades in the Baroque pearl bracelet and the green of my new earrings by Lizzie Fortunato. I’m not sure how this fun brand crossed my radar, but I love their aesthetic.

RIBBED HIGH NECK T-SHIRT size M / QUILTED VEST size M / SIMILAR CUFFED JEANS / LOW BOOTIES / TOTE BAG / NECKLACE / SIMILAR BELT / SIMILAR EARRINGS

Yesterday, I had to run to the pharmacy, and then I hung out at home to work. I wore a simple long-sleeve tee, a lightweight vest, and my J. Jill cuffed jeans, which appear to be sold out (similar jeans here). I added my new Cuyana tote bag and low suede booties, along with an old coordinating belt from the wardrobe archives, earrings, and a silver necklace. I could have skipped any accessories because I was only racing into CVS and then staying home for the rest of the day, but the earrings, belt, and necklace helped my outfit feel finished.

A reader commented last week that she doesn’t dress up “just to go shopping”, but I believe that’s precisely when we need to make an effort. I encourage you to get up, dress up, and show up! Every day is a special occasion, so dress to express your vibrant self, and don’t save your best or favorite pieces for a day that may never come.

It only takes a moment to add a few accessories or interesting layers to your look, which makes the difference between simply getting dressed and styling your outfit.

How is your style changing this year?

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65 Comments

  1. I am enjoying your posts very much. I can relate. I’m retired 5 years now from being a flight attendant and clothing was simple when I worked and traveled. I now have gotten rid of all the things that no longer work as I have a much more casual life. The info you’ve given has been helpful as I’m now recreating a 65 year old who very happy with her new life.

    1. So happy you like these posts!

  2. I love your Saturday outfit–simple yet so put together! I’m interested in how you tied that beautiful blue scarf.

    1. That was a simple square folded in half, draped triangle pointing down back and fronts tied in a knot. I’m working on a post about scarves.

  3. I love how you combine pieces! I am a retired teacher with a small clothing budget but I take pictures of your outfits and then go to my closet and put outfits together combining similar pieces and colors I never would have thought of….and I feel like I’m wearing brand-new outfits. Thank you

  4. Love this post and all your outfits! Such an inspiration.
    This year I’m going to stop buying (as much) and start wearing. I want to take the time to put together different outfits, as you did, from existing pieces.
    Also, I want to use inspiration pieces to build an outfit. I have quite a collection of scarves, and jewelry that I love. I want to concentrate on taking one piece at a time, that I love and building an outfit around that piece. Should be fun!
    I’m going to “copy” some of your outfits too! Thanks Jennifer!

    1. It is fun to do that! Enjoy

  5. I also love all of the outfits you wore, and I’d wear each one of them, except in a plus size version. I lost 40 pounds this past year, but still a plus size, so I bought myself a lot of basics and unique pieces to replace the clothes that were too big. One thing I did notice, and this is related to you’re wearing a scarf to tone down the black, is that I don’t want to wear a lot of black anymore. It used to look great on me, but now that I’m in my sixties, I feel that black is too harsh for my face and changing skin translucency. So I’ve bought a lot of different colors, and my resolution this year is to have fun creating new outfits. Thanks for the inspiration!

    1. Congrats on the weight loss and buying basics as well as some unique pieces for your new shape! So often, women forget those are what make fashion a delight to wear.

  6. I agree! We need to stop “saving”outfits and just wear them to look and feel good even when there is no event or occasion!
    It’s taken me a lot of years to realize this and I’m happy to know you are enlightening other women with this advice. Now I just have to remove more of my worn items.

  7. For years i had work clothes and stay at home clothes. Raising kids and teaching i neglected my self and wardrobe ..
    now that I’m older, retired l and can shop for me ,instead of four kids too, I find that I want to loook nice even at home ..! Or runnig errands .
    whatever are we saving things for now ??
    I always wear earrings , necklace and accessories and pick out more fun outfits instead of just old jeans and a sweatshirt as I see so many older ladies wearing to store and dr etc… i feel better, look better , and have a better outloook on life .
    you have helped ne remember that dressing up, showing up matters evenfor ourselves and our spouses at home . Thank you
    It also helps when we get compliments from hubby or friends!

  8. I bought three of the high neck long sleeve tees! I got the grey, black and off white ones. Mine are so tattered looking around the neck, not even good enough for donation. It is supposed to snow tonight and tomorrow with a high of 21 degrees. Going to wear my Athleta merino wool and cashmere sweater as it is so soft and warm. Perfect for a really cold day for our dog walk. You looked great in every single outfit Jennifer.

    1. Thank you Sydney. Stay warm!

  9. Like many of your other readers, I really enjoy your what I wore outfits and the occasions you dressed for. With many of those similar type basics in my closet, you’ve given me some inspiration to put certain things together.

  10. Hi Jennifer! I also have enjoyed the outfits you have worn this week-for those of us wanting to get the most out of current closet, it really helps! I especially love the red sweater look and the look with the trench coat, thank you!

  11. I find it very inspirational when you share your daily outfits as I am similar in height and complexion as you. I am ordering the wine knit sweater coat . It looks very good on you ! I’m also ordering some scarves to wear with many of the black tops I have . You’ve helped me out so much and I look forward to all your posts but especially what you wear on a daily basis .
    Could you send me a link to your glasses ? I think they would suit me too as I also have a square shaped face.
    Thanks so much in advance !

  12. I love your “shake up” Jennifer! I can recreate almost each outfit, but have never put my similar pieces together as you have shown. I’d love to see you feature more of your accessorizing and outfitting talent. It is so inspiring to know that I can shop my closet. I’d almost given away my long burgandy Chicos sweater and now I can’t wait to pull it out and wear it as you have. I might be twinning you several times this week!

  13. Jennifer, Thanks for sharing all your gorgeous outfits. What I love is, they aren’t complicated, but simple, thoughtful, and pack a punch….Looking forward to seeing your style in 2025.

  14. beth byrd says:

    The belted sweater coat is such a stunning look for you!!

    1. Thanks Beth. I may need to wear it out of the house that way but add shoes and makeup.

  15. The link for the tinted brow gel took me to the lipstick – as did the lipstick link. I’d love to know what brow gel you use.

  16. First, the link to your brow gel takes me to the lipstick. I left my makeup bag at my son’s house yesterday, so I need to resupply today!🙃
    Love all your outfits! It’s fun to put a new spin on old favorites. I’m going to pull out a few things I haven’t worn for awhile & hang on the back of the door to work into my outfits this week. If I’m still uninspired, I guess it’s time to bid them a fond farewell.

  17. I really liked your post today. I have similar outfits and now I know how to make my look more interesting. I especially liked the scarf on the v-necked Quince sweater and the leopard spotted belt.

  18. Every outfit looks wonderful, as always! I think my favorite is the jeans with blue scarf! Happy New Year!