Monday Musings- Editing Your Wardrobe To Redefine Your Style
Happy Monday, ladies! Today’s musing is pretty stream-of-consciousness, so grab another cup of coffee… you may need it to follow along. The change of season is a great time to cull your wardrobe, so that’s what I’ve started to do. In the process, I’m realizing that I’ve gotten into a style rut. I’m not the same woman I was last fall, and my style objectives have certainly changed, but it’s more than that. I’m sure living out of a suitcase for three weeks has contributed to my boredom, but I think a change has been in the wind for longer than that. Let’s talk about editing your wardrobe to redefine your style…here’s my story.

I’ve been reworking my 3-words to refine my personal style so that my closet can once again be filled with things that represent the woman I want the world to see. As I’m going through and identifying what I reach for all the time and actually wear, I see too much sameness for my taste. Oh sure, there needs to be cohesiveness, but there shouldn’t be boredom. Just how many pairs of jeans does one woman need in her closet?
My love of neutrals has not gone away by any means, but I have been slowly adding some color into my wardrobe and am enjoying it. My style has narrowed down to a somewhat limited classic look over the last few years, and I’ve begun to miss the fun and creativity of other styles. Don’t get me wrong; I will always have classic as a big part of my style equation because I love it. I just want more.

I just bought these semi-classic black and ivory wide-leg pants, and I adore them. I say semi because they’re not a trouser. They’re a pull-on style in classic Houndstooth, but they do make me feel different because I’m most often in jeans. They have a slight feminine vibe because the leg is swishy and wide. I love that, so I’d like to lean into more feminine styling without going girly.
So, how could I make this outfit more interesting? Lots of ways. I could add a color on top, and I already have some ideas about that. I could carry a unique handbag…which reminds me I need to go through my purses and bring out my fall ones.
I did add a deeper lip color, and that changes things from my usual. But I’m looking for more, so I’ll be combing through my accessories next because they are what really give an outfit its personality for me.

I realize I could have worn my black hat, which would have added some attitude. I also could have put a belt over my sweater. My Jennifer pearls would have jazzed it up because they’re anything but classic. I felt totally like myself in this outfit, and it was easy to wear so perhaps what I need is some subtle tweaking rather than a radical shift.
As a fashion blogger, I end up with things in my closet that aren’t my style, so my hope is that as I weed those out and donate them, I will get more clarity on where I want my style to go. It’s still warm here, so there’s no rush, but I certainly feel an urgency. I just need to go slow enough to listen to my gut instinct.

I’m struggling the most with my third style word, which describes and defines the aspirational part of your style formula. It’s the most personal of the words, so it makes sense that that’s where I’m stumbling. It feels like fine-tuning, and a subtle shift may make a big difference, so I’m excited to continue and see what happens. Stay tuned…
** I plan to take a few upcoming Wednesdays off, so don’t be surprised when you don’t see an email from me. I’m rethinking my content calendar and need some time for an upcoming project.
I had a reader mention that she always buys her own gifts because her husband buys her things she will never wear. That’s certainly a way to tweak your style in a new and unexpected way! Another reader mentioned she likes it when her husband picks out her clothes.
What about you?
Have you tweaked your style lately?

What are the first two words for your wardrobe?
Classic and polished
I ordered these pants yesterday. They are out of my comfort zone a bit since they have a wider leg and I usually wear a straight leg pant or jean. Thank you for inspiring me to try something new. The black and white sold me.
I like those pants on you! They are classic, understated , and sleek.
I like the clogs , they balance well on your physique. I envision a classic handbag like Tory Burch makes, and possibly a tiny neck scarf. Nice.
i love the pants and just bought an almost identical pair on amazon. a yellow sweater would be pretty, and i would change the shoes—they seem too “sturdy” for palazzo pants. maybe a low heel or slingback? push the sleeves up a little, and add a classic watch. pretty girl, pretty outfit!!
I had written a long comment earlier and them my internet went down and I guess it got lost!
Firstly – I really like those pants and it is something that I would wear. I stopped buying jeans years ago when manufacturers were adding excessive stretch and each year I’ve planned to buy a pair but then I find something I prefer in a cotton or wool blend or ponte or just recently fuax leather and to be honest I haven’t missed wearing jeans.
I’ve re-evaluated my style again recently and am back to what I’ve always been – a bit classic, a bit sophisticated and a bit dramatic.
I’m looking forward to seeing where your style direction takes you Jennifer.
Personally what I found is; if one also learns the styles that exist (not to be confused with trends) they may surprise themselves, as similar to body types they are a mix. In other words, do not pigeon-hole yourself thinking that your style or what you wear is just Classic when it can also have a nod towards another. i.e.: A jacket that is designed to tick all the boxes of it being a Classic however if it is embellished with soutache cord, then IMO it also leans towards Parisian, Vintage, Bo-Ho to name three. Last but not least; on the subject of culling a wardrobe/closet recently did it for winter outerwear and donated it to a women’s shelter. -Brenda-
I like to donate my things to our women’s shelter too!
Whether one uses three words or can “picture” their look is really helpful. I’ve moved beyond what appears like a great item because of one wrong detail. Ex: a double breasted blazer that cuts straight across is a big No. I’ll only do double breasted if both sides have a slight angled cut that creates an inverted V when open or buttoned. While being a natural-classic, “detailed” is one of my words. I love a puffer vest…. but only ones with a slim silhouette, nice finished details and my 3rd word “comfortable”. For me “detailed” is usually the deal-breaker! Detail can be color, fabric, finishes, cut, etc. It’s the style word when standing infront of a mirror that makes me say “eh” something isn’t right. So I begin the detail search and find it. 4-H sewing has left a lasting scar…. don’t even show me plaid that doesn’t match!!!!
J.Jill is having their annual Gently Worn Clothing Drive Oct 12-18, it’s part of of their Compassion Fund which helps support women in need. You get $10 off, check their website for specific details. I’ve used this as a great way to pass along some of my better used clothing when cleaning out my closet.
I just did the same thing yesterday for a few itmes
JENNIFER, YOU ARE A BEAUTIFUL WOMAN & I LOVE THE LOOK YOU ARE GOING FOR. I HAVE ALWAYS LOVED A CLASSIC BLACK/IVORY CHECK PANT & I AM CURRENTLY ON THE LOOKOUT FOR A NEW PAIR. I WOULD ADD (I KNOW YOU LOVE SILVER JEWERLY) A COUPLE OF TAILORED SILVER CHAINS & MAYBE A SILVER CUFF BUT I WOULD DEFINITELY DITCH THE CLOGS & ADD A NICE PAIR OF CLASSIC BLACK LOAFERSā¦ā¦THINK KATE MIDDLETON OR JACKIE KENNEDY.
I love the pants! I have some wide leg pants that I have purchased in the last year or so to wear when traveling, but havenāt worn them a lot at home. I am 75 and most of my friends are not wearing them. I am not particularly fashion forward, but I love the comfort and ease of the wider leg, and they are so much easier to get on and off compared to the skinnies. I am a Gemini and feel sometimes like I mirror that in my clothing choices. Usually I am all about casual and comfortable (like elastic waists!) Each season I weed items out, and usually with each season I buy a classic piece, sometimes with bit of trendy, as in ruffled cuffs on a Talbotās cardigan. Love your dressing room posts, and looking forward to seeing how you approach your goal of making some changes!
Coincidently, I just counted my jeans this morning – 10 pairs! It’s all I wear and I am bored to death. I wish I could find trousers that fit, or had a reason to wear a skirt. I have been getting rid of clothes I don’t feel my best in. Out goes anything thin, clingy, floppy. Oh, and everyone gets cash for birthdays/holidays. My peeps want to be able to live out of a suitcase or are in the death cleaning phase.
Lol. I get the death cleaning phase. I need to get into it because it feels so good to clear out!
Hi Jennifer, great post today. Looks like a lot of us are feeling the same way, wanting to refine and redefine our wardrobes to fit our lifestyle and mood. I’ve been thinning things out in the closet and am working hard to find new things in my Winter color palette. Jeans or black knit pants plus a tee or blouse topped with a cardigan, cute shoes and favorite jewelry seems to be my uniform for most any occasion, with a scarf added if it’s cool enough. I do love color and print and also have a weakness for 60’s and 70’s band graphic tees, but am working toward more solid pieces. My biggest challenge is the warm weather here in San Diego, it makes layering really tough for much of the year. Also, I have a larger frame and bust and don’t want to look matronly. My style words include, simple, classic and polished, but like you, I’d like to include feminine. I so appreciate that you know what we’re thinking and look forward to more posts on this subject! Hope you enjoyed Portugal. :).
It was great, thanks.
I would love you to show us everything you took to Portugal for 3 weeks in a carry on.
Do you think that would be possible, please?
Iām going to try. Be warned. It is boring
Well, if my goal is to remain relevant, not stagnate, then itās necessary to have an open mind to reevaluate and make changes. I like your attitude and approach to life. A new brighter color top or a fresh lip color sounds fun. Sometimes, the littlest changes can have the biggest impact.
My husband and I donāt exchange gifts but will plan a weekend getaway to celebrate a special event.
I love your look and I love the pants, Jennifer. But I am in the same place – I like my classic pieces, but my style needs something more. I am looking at adding a colorful third layer on top. Some print, lightweight jackets are what I am thinking about to add interest and more personality to my outfits. Since my retirement and then Covid, I have been re-thinking and re-working my wardrobe. It is slowly coming together, but I am still figuring it out.
Scarves ! around ones neck, waist and or purse handle
Love this “entry” in your blog! I constantly struggle with too many clothes and finding my true style. Sometimes I feel like wiping everything out and donating, and just keeping what I’ve recently bought, because I know it fits and I love it.; for now.
I try to edit my wardrobe with every change of season. Seems I still end up with tons of clothes. Jeans….yes, too many. I have 9 “active” pairs, yet I don’t wear jeans that often! Go figure! I dream of a streamlined closet with only things I absolutely love in it. (Marie Condo style). I just can’t seem to get there! A work in progress, always!
I love the outfit you feature; it looks fantastic on you. I look forward to this continuing conversation!
Hi Jennifer. LOVE the tweed pants and they look fabulous on you. You look like you really like them, too.
I have just finished a “wardrobe reboot” and have some tips that may help someone:
1. Create a Pinterest board with styles that you LOVE and can see yourself living in. They may be very similar to what you wear now, but often are a real tell as to what draws you. My three words are “Classic”, “Casual” and “Comfortable.”
2. Determine how you spend your time. This will show you what you need and what you don’t.
3. Using your Pinterest board, divide your current wardrobe into LOVEs, Maybes and Nos.
4. Clean your closet before you add your Loves back in. You would be amazed at what is lurking in it.
5. My closet holds 95% of my year around wardrobe and I limit the number of hangers I have. I “doom tag” with slips of paper over the hanger hook. Some turn the hangers around but I like the visuals of the papers. Tags are taken off when I wear the item. Those with tags at the end of the season were not worn and should be examined for future need. Some exceptions are formal wear and those items out of the current season. For shoes I have tagged with blue painters tape inside one of the shoe which is removed (when I remember, LOL) when wearing.
6. Once the closet is reloaded, make a list on your phone of items needed to be replaced or added to pull outfits together. Do NOT buy anything that is not on the list!
I hope this helps someone as it has really helped me. I have always done fall and spring wardrobe “switches” and purges, but this is the first time I used Pinterest to determine my style. Keep in mind, style and tastes change so continually update your Pinterest board as desired.
Have a great day and keep bringing on the wonderful inspiration that you so beautifully do!
This is fabulous Virginia, thanks!
Hi Jennifer,
I love those pants they are so fun! Looking forward to the new changes and l hope you had a beautiful vacation!
I question the idea I am dressing to show the world something. My style is what pleases me. The world will think what it thinks. Comfortable restrained boho. I know I’ve hit the sweet spot when what I’m wearing makes me happy. My attitude is that anyone who doesn’t like how I look should just look at somebody else.
I am also rethinking my closet and this article was very timely for me. I do shop in JJill and Talbots because they work for my size and they are local, I also order from Nordstrom, especially for shoes. We live in a casual southern environment so most of my clothes are classic casual. I have along way to go to find two more words. Thank you.
Jennifer, I always love your columns and find them helpful, but todayās hit me like a ton of bricks. Over the past couple years, switching into retirement, living in a new community, I have purchased so many items trying to ādressā who I am now and Iām not sure where I have landed. I just looked in my closet and think a stranger would believe it belongs to someone with a multiple personality disorder. After reading todayās post I need to seriously try on everything and figure out if it should be owned by me. As it is, I have lots of clothes, but ānothing to wear.ā š© Thanks for the wake-up call, Jo
I hear you! It’s so easy for that to happen. Start with what you do wear all the time and you’ll end up finding the orphans and imposters who don’t belong there. That’s what I’m doing.
I will try againā¦.please resubscribe me to your emails. I enjoy them every day
I have spent much of my life as a school administrator and am delighted to have more fun with clothes. I have explored new brands and begun sewing pants, tops and jackets. I now look for clothes and shoes that are comfy in p and fun. Thanks for signing me back upā¦.i
You appear on my email list, so if youāre not getting them, perhaps check your spam folder.
The pants to me are menswear-looking to me, so not a feminine look even with the drape. For those of us who are not image consultants, our lives (and style) are grounded more in practicality and how we live. As you’ve been buying jeans and more jeans over the past few years, I’ve thought a lot about “how many jeans does one woman need” for my own closet — and I live in jeans except in the summer. Most of us also don’t need a dozen or more white shirts. I hope that your answer to your questioning is framed by both reality and sustainability as well as your desire for change.
I love this outfit! Iād probably add a necklace, push up the arms of the sweater and add a fun watch or bracelet and half tuck the front of the sweater – for my style. My hubby and I gave up a long time ago on gift giving for each other. Instead we plan a getaway or activity we want to do to celebrate. Thanks for all the great advice!
Very timely! I started a wardrobe re-work last week, beginning with pants. I came up with seventeen (!) pairs that are now in the thrift store. Those were all ones that I canāt wear (size), wouldnāt wear (style, dated), or shouldnāt wear (worn, faded). Whew. On to the next sections.
Good for you!!
Love those pants, feminine but not to girly. As my kids would say when I had a real job, prior to retiring early and working as a Pilates, Barre & Yoga instructor, everyday was a pencil skirt with blouse or tank, sweater or blazer and pumps – boring but very professional. Now that I have “retired” and am doing what I love, I’m in jeans and a tank, graphic tees or occasionally a blouses or sweater but still on the struggle bus to look completely put together, I still need to figure it out.
I’ve been feeling the need for some wardrobe changes also. I certainly wear jeans way to often but they are just so easy! Everyone in the NW where I live all seem to wear leggings and workout clothes everywhere. I like your comfy tweed pants. That would be a great start for something different. I’ve been starting going through my closet so I hope to make some changes.
My style is still classic, chic which suits my over 60 age. I have gone to more colorful clothes since my hair is now light silver/white. I wear less neutrals , except black looks good on me now. I switched to white shirts instead of cream or off white.
My husband will give me a gift card for birthday or Christmas for clothes. If I like a certain clothes item I share a link of it. We play Santa for each other. We give each other a suggested list for Christmas. So it still is a surprise at Christmas. My husband likes to give me a list of what he would like as well.
I really like your outfit today. I wish the pants came in petite.
Your thoughts about reworking your closet and “how many pairs of jeans do you really need” struck a cord with me. Can’t wait for you to continue….
Naniscah Apperson
I have tweaked my wardrobe with the fall turnover. I went through my sweaters and only kept the ones that spoke to my current style. Sweaters that are shorter remained, while any longer ones were donated. The reason for this change, a change in pant style. I switched over to straight in the spring and donated any skinnies. Straight leg looks better with a shorter top and I do not mean cropped. Being a slight pear shape, the shorter tops do not come over my hips, both bringing attention to them and emphasizing the size difference. Tops with shoulder interest, boat necks, square necks balance out my top and bottom half.
The surprising change is, I recently bought three pairs of pants and am enjoying wearing them. As a die hard jean girl, this comes as a surprise, even to me. Iām not giving up my jeans but branching out.
Branching out is a good thing. Iām doing that too.
Thanks for the great blog today. Iām bored with my wardrobe. I donāt want to be the same person as last winter. I think it would be great if you showed us an outfit using different accessories and tweaks to spruce things up. I remember years ago you did this and I really like it.
That’s a great idea
Well, to change your outfit about and add some femininity, Iād go for color in the top-something unexpected maybe a light blue? Then definitely add the pearls you talked about and the belt, maybe. I think Iād button up a short cardi and use that as a top. Then Iād change the shoes. Heavier clogs like you have on are masculine looking. A kitten heel or cute platform sneaker even would work.
I know what you mean about boredom with your wardrobe. Time to chang3 over to fall stuff here and excited to see what Ive got that does and doesnāt work for me any more.
I always go for the fun factor! Check out Zuri dresses which are ethically sourced in Kenya.
I love this outfit! I am trying to find my clothes style after retirement and itās very hard. A lot of my problem is shoes I have terrible bunions on both feet and I come from you donāt look dressed up unless you have on heels š now all I can were is hokas. Itās hard to dress an outfit up for me and Iām also 5ā2 which I need petites! I feel like Iām loosing all the way around. I donāt always want to look like a bag lady!
Shoes can and make or break many outfits. A longer pant that covers your shoe may help.
I did this several years ago, we called it upcycling your closet. It made a lot of sense as the stylist pointed out we wear about 20% of our clothes and really love about 10%. We gathered basics and added a signature piece and then tweaked accessories. It was a fun exercise in streamlining and feeling confident in new looks!
Jane
I love these pants on you. Yes, they are more classic than jeans and I am drawn to classic, but I think they also give a better proportion to your outfit. Perhaps, it is the photography, but you look taller. In addition, you tend toward very pale neutrals and this black top and black patterned pants give you more presence. By that I mean putting your best real self out there as you go about your day; not to draw attention, not in an egocentric way, but as a whole woman who knows who she is (or whose clothes tell her who she is on the days when she is too tired to remember).
Gosh, I should take this to heart for myself.
The clogs do add a few inches which is one if the reasons I love them. I do love wearing black and shoes away from it as I got older, but now with my hair so silver, Iām circling back to it.
I love those pants! They look very good on you. Im allergic to wool so would need to find a different top for them. This is a great classic outfit.
Good morning……I started changing my closet over and didn’t finish. I’m finding I have too much stuff (too many choices) and then I put an outfit on and realize later that it could have looked even better. I think I’m going to go through my items (accessory/third piece) that can be incorporated into an outfit to give it that “spark” it needs to elevate or make it different (I’ve seen some of yours in your pictures and it does make a difference. I think I need to get better organized and do some outfit paring as well.
Thanks for the inspiration, Jennifer. Iāve worked really hard to rationalize my wardrobe to fit my current lifestyle, body type and coloring. āTweaksā is a good way to describe an approach to keep things from getting too boring.
I am going to focus more on adding accessories. The right ones are seasonless, versatile, and pack easily for a trip. Itās an easy way to add color and interest.
I feel compelled to pull out my silk scarf collection. These havenāt been on trend, but I saw a woman with a beautiful silk over a sweater this weekend. It was just the pop a casual outfit needed. Back on the office days, Iād treat myself to a classic silk on trips as they were easy to pack and would remind me of the place. I might give some of my favorites a little tour!
I recommend Allison Bournsteinās new book āWear It Well.ā She is the creator of the three word system. She sheds new light on going through your closet, especially the āneverā pile, to really focus on why we donāt wear certain items. I find style to be constantly evolving. Some of the edgy/punk items I used to love now seem costumey to me and Iām circling back to more of the āJ Crew of oldā items worn in a minimalist way. Iāve figured out Iāve always liked the straight lines and boyishness of those styles. Thinking back those styles were very unisex. Iāve also had a change in weight and I realize the styles I used to wear no longer work.
I must have missed your first blog on 3 words so I went and read it, so interesting! I have been trying to pare down my wardrobe and feel my style has been changing. I love clothes with a little twist, like clothes from Evereve, and WHBM. I like classic with an edge. I know I want fewer clothes but ones I love. I will have to do some thinking on my 3 words. Thank you for inspiring us!
Good morning Jennifer, I like your idea about reassessing my wardrobe choices. The pants you modeled today look so comfortable, stylish and classic. I know what you mean about too many jeans. I bought a new pair last week and have decided thatās it for the rest of the year. A day off during the week is an excellent mental health day which many of us fail to do.
Have a great day!
Happy Monday Pat
I understand the need for change and re-evaluation. I didn’t quite understand how much of an ongoing process this would be and that it would impact so much of my life. I look foward to hearing where your journey takes you.
I do like what you are wearing and I would have liked your black hat with it. Curious what jewelry you would pick. My jewelry choices appear to be changing too.
I really like the pants and will have a look at that blend. I have been a ‘feminine style without the girly’ for years, and it is often hard to describe but that says it rather well. I don’t feel finished without a scarf, jewellery or other softening touch. This explains why I have never felt right in a jean jacket or chore jacket style. It wasn’t until I found out my personality type (ESFJ) that made it all make sense and when I look back has always been there, but others influence has sometimes had the wrong effect. Not anymore, I can tweak but not really change how I feel in something and how I express myself and feel totally ‘me’. Sorry about the rambling, but just want to say it must be hard with all the people to please with a blog.
I laughed out loud when I read about the reader who buys her own gifts, so true here as well, it just works out so much better. It only works the other way if it is something I have vocalized on numerous occasions and then a ‘surprise’ is just right.
Good luck finding your new path to feeling yourself
Thatās why Saturdays mannequin was so out of my style wheelhouse.
I had better tweak my style! Itās become pitiful. I need to figure out where Iām going. Your outfit there is great. I love it.
When I worked I had a very easy predictable (ugh) style – tee or shirt, blazer and slacks or dark jeans depending on my mood, the weather etc. I did incorporate some fun jewelry into my style though.
Now I’m retired- and I’m a jeans woman ( light, natural mid-blue and deep dark blue or black- even grey). I do vary my tops and try to add that third piece or a scarf. Still pretty predictable but I’m comfortable!
My life ( otgervthan many exercise classes) revolves around book club, my herb garden or babysitting family dogs or children. We do have lunches out but nowhere needed to dress up, so to speak
I love your outfit today! The pants do add a bit of feminine but not too much! Now I am a straight up and down body type, so I need something to break that up. Your idea of a belt is a good one if it’s the right belt. Even a white shirt peaking out below the sweater….anything to break up that line, for me that is. I also have the lippy in “Fashion” and love it although it is a darker color, it is great for Fall.