Monday Musings on Dressing For How You Need To Feel
Happy Monday, ladies. Today, I’m thinking about the times when your body demands a total detour from your usual daily uniform. We spend a lot of time engineering outfits based on the weather, the calendar, or our proportions, but sometimes the most important question in the morning is simply: How do I need my clothes to make me feel today?
Last Friday, I woke up feeling like I’d been hit by something slow-moving but thorough. My bones ached in that deep, dull way that’s hard to explain unless you’ve been there. My doctor suspects it’s a side effect of my bone density medication, so I had an X-ray scheduled to check on my hips.
Naturally, I stood in my closet, and my hand automatically reached for my usual summer fallback…linen pants and a striped shirt.
The Shift From Structure To Softness
Linen pants and a striped shirt signal structure, and last Friday, my body was practically begging for softness. Everything hurt. I needed ease, comfort, and a little bit of feminine energy to pull myself together.
I put the pants back and pulled out a white balloon skirt instead. Because it was hot outside, the volume of the skirt felt airy and free rather than restrictive.
To keep the outfit balanced, I added a simple tank top. The key here was the length… it was cropped at exactly the right spot on my torso, so there was absolutely no need to tuck it in and add bulk around my waist. I slipped on comfortable sandals and a pair of shiny earrings, but the outfit still needed a final anchor.
I dug through my wardrobe archives and found this soft leather flower belt. It brought in some texture and added a touch of whimsy that I didn’t know I needed. Sometimes, a tiny, unexpected detail is exactly the trick to lift a neutral outfit out of a slump when you don’t have the energy for major styling.
Why Mood Trumps Your Style Words
I’ve always believed it’s incredibly helpful to choose three specific style words to keep your wardrobe cohesive. It gives you an excellent filter so when you’re out shopping, you can simply ask yourself whether a piece aligns with those words before taking it to the register.
But some mornings, getting dressed has nothing to do with checking the right style boxes. It’s entirely about what you need from your clothes to get through the next twelve hours.
Maybe you need softness against your skin, a bit of rigid structure to keep you focused, more physical ease, a pop of color, or something just feminine enough to lift your spirits without making you feel like you’re playing dress-up.
We talk constantly here on the blog about dressing for our body shapes, our color palettes, personal contrast levels, our proportions, and our daily schedules. All of that matters, of course. But your mood matters just as much. There are days when the weather forecast and your calendar only tell half the story. The better question to ask yourself in the closet is: What will help me move through this particular day with a little more comfort and confidence?
Using Clothes As A Practical Tool
If you’re feeling a bit exposed or uncertain about the day ahead, you might automatically reach for structure with a third piece like a great jacket, a stronger color, or a shoe that makes you feel steady on your feet. Black always makes me feel a bit more powerful, so that’s usually my starting point when I need a little armor.
But if you’re tired or just feeling a bit tender, you need the opposite. You need soft fabrics, an easy waistband, a skirt that actually moves with you, or a small detail that simply makes you smile when you catch yourself in the mirror.
That’s not frivolous, by the way. It’s highly practical. Clothes sit on our bodies all day, and they absolutely change how we feel.
The next time you get dressed, look past the weather and the to-do list for a second, and ask yourself what you actually need from your clothes today. Is it ease, softness, strength, color, or maybe a little bit of whimsy?
Some days, the right outfit isn’t the one that makes the most sense on paper. It’s the one that helps you feel just a little more ready to face the day.
Over To You: What’s Your Comfort Outfit?
The next time you’re standing in your closet feeling less than 100%, try looking past the calendar and listen to what your body is asking for. There is actually a whole field of fashion psychology dedicated to this concept. Scientists call it enclothed cognition, which is just a fancy way of saying that what we wear directly impacts our mindset. But we don’t need a study to tell us that.
How do you handle the days when your physical comfort or mood doesn’t match your schedule? Do you have a specific piece you reach for when you need a little extra comfort or a confidence boost? Let’s talk about it in the comments.
Jennifer,
I read your column almost daily. Although I don’t always agree on everything, I love to see how you style things. This black top and white balloon skirt look amazing on you! Smart, sophisticated & styled so you could go anywhere.
Thanks Lynn, Please join the conversation, we’d love to hear more from you.
I went to a surgeon to schedule surgery on a hernia I have had several years and was told by one doctor that it was inoperable. The surgeon warned me that it would be a painful surgery and painful recovery. Great. It’s slightly above my waist and sometimes makes wearing slacks or jeans uncomfortable. I have several pairs of Wit and Wisdom jeans with elastic on the inside waistband, and they are the most comfortable jeans I have been able to wear. I’m looking forward to the surgery and recovery being over so I can wear everything else in my closet, but I thought it might be nice to share this with your readers.
Hi Jennifer, I love this outfit and your hair looks fantastic! As the kids say these days, it’s “giving” fresh, energy! I’m currently in a hair rut and you’ve given me inspiration for my next haircut!
Yay!
I’d love for you to address hem lengths sometime in the future. It seems to me that sometimes a longer hem length tends to make someone frumpy. I’m famailiar with the 1/3 – 2/3 rule of thumb but unsure how it should be used when the long length of skirts/dresses makes one appear enveloped by too much fabric, especially in the white skirt on you. (Sorry, IMO). I’m 5’5″, medium build. I’ve been told that a good length for me is skimming my knee caps or just below. Thankfully, my legs are still in good shape and I don’t mind showing them. Please advise.
Hem lengths generally look most flattering when they hit a spot where your leg narrows. Then you need to consider personal preference because being bound by rules can take some of the joy out of getting dressed. I like longer skirts because they elongate the look of bottom third.
I love that outfit on you! So chic and it also looks comfortable. Thanks for the inspiration!
Hi Jennifer, love the outfit. It really looks great on you! Always love your posts.
I just wanted to share my little success story related to osteoporosis. The last time I had my Dexa scan over three years ago, I was diagnosed with osteoporosis in both hips. I decided I did not want to take any of the medications offered due to the side effects and strike out on my own to see if I could improve it with more exercise, nutrition and supplements. My diet has always been pretty good, I have two cups of whole milk kefir every day and just added another 1/2 – 1 cup of homemade yogurt, cultured for 36 hours. In addition, I increased by vitamin D intake (natural fish oil sourced) to ~3000 IU per day and I added vitamin K2 Mk-7 (sourced from natto) to this regimen along with magnesium and my usual multivitamin. Woe and behold, I had my follow-up Dexa scan last Fall and I managed to reverse my osteoporosis to osteopenia in both hips. I am beyond thrilled and will continue this regimen in the hope that I will be able to reverse the osteopenia, too. My doctor was amazed.
I hope your hips are ok and the medication will help you. Just thought I would share my experience. All the best!
That is amazing Cherie and gives me hope. Thanks so mucg for sharing!!
You look wonderful, Jennifer! Yes, for me, at 70, comfort is foremost, but I try to look polished with fabrics and accessories. I have very sensitive, very pale skin, so I appreciate soft fabrics, a collar, sleeves (preferably 3/4). I was fairly dressed up yesterday for a retirement event and reception, and I wanted to throw my 1 in heels in the trash when I got home! I have no tolerance for uncomfortable shoes anymore…
I am in the same camp as you about shoes!!
Jennifer, this is the cutest outfit ever! Hope that you are feeling better soon! I’ve been on osteoporosis medication for many years. It takes a bit to find the right fit. I’m currently on a Prolia injection every six months. This works for me. Making sure we take care of ourselves as we age is our biggest priority, as I see it. Keeps us moving, feeling well and enjoying our lives/families.
I agree
You look fabulous. The recent haircut fits you well.
I really like this outfit on you. You look stylish, modern and youthful. Very nice!!!
Thanks so much
I am sorry you were not feeling well.
You look amazing this picture.
Your hair looks great, and the outfit is spot on!
Comfortable for the win!
When I’m thinking about what to wear, I ask myself two questions before I get to my style words and how to pull items together.
First, what’s appropriate for what I’m doing and where I will be.
Second, are there any comfort issues.
I love this post! How do I need to feel today!?! Thanks.
Love the outfit you put together!
Hope you feel better soon. I’m avoiding medication for my bones for that very reason; the side effects. Don’t know if it’s worth it. I hope that the meds are doing their job.
I agree with certain clothes for certain times. I’ve probably gotten dressed for my mood many times, but without really thinking about it.
When I’m feeling happy, I reach for wide leg “swing” capris and an overblouse.
An outfit like that feels free and breezy. (in the summer).
When I want comfort, I don’t want anything tight or clingy. I will reach for a cozy soft loose sweater or sweatshirt, or a soft loungewear set.
what med are you on for bone heath? I did Evenity for a year and then switched to Reclast for last two years. I didn’t see improvement this year but didn’t get worse. I have been following Kevin Ellis with a new supplement by Healthy Bones and hope his products will help too.
I wish you well, and I do change up my outfits for mood as well as comfort.
Blessings and best!
Mary Packnick
Lebanon, NH
I’m on Teraparatide injections daily.
That outfit looks perfect on you! Black and white is always a good choice.
I find myself reaching for soft knit athleisure outfits lately… Loose elastic waist pants with a matching tee. Soma makes some nice, comfy and well made sets. I can lounge at home or with the right accessories, wear the set out to run errands or even to hang with friends.
It sounds like the scary negative side effects of Prolia that are reported online. I was very worried when I started that drug, but have not had that experience. I wish you the best.
So sorry to read that you’re not feeling 100%- hopefully you will soon.
As others have commented, you really look fantastic in this outfit- sandals, hair, all of it. And it looks so comfortable and relaxed!
Jennifer, your post made me change my mind about the outfit that I was going to wear tomorrow. Instead of black trousers, a white button-down shirt, red blazer and black flats, I’m going to be wearing white palazzo pant, a matching soft knit sleeveless top, a white chiffon duster decorated with watercolor-style scarlet macaws, red sun hat and sandals. It’s summer, a fine time for whimsy, and maybe people will smile when they see me wearing it.
I think your flower belt is adorable and I love the color of your nail polish. I hope you are feeling better today, too.
I adore the sound of your outfit!!
Hello Jennifer!
It is 3:49pm EST and I am just now sitting down for the first time since my coffee this morning and hit the ground running hard.
Did anyone else happen to mention the link for ‘outfit details here’ isn’t working?
BTW, you look terrific in that black top – is it because the sun glasses balance everything? I know as a soft summer we try to ‘avoid’ wearing black, but in case no one told you today, you look beautiful:)
With gratitude for all you do,
Brenda
Thanks Brenda. The link is working for me. Please try again. I use those color rules as tools and don’t let them dictate what I can or can’t wear. I love black and don’t plan to stop wearing it 😉
I love this outfit on you! I hope you are feeling better soon.
I absolutely love your outfit choice today. When I’m having a day that requires softness against my skin, I always choose a long soft maxi skirt with a tee or tank top, in the winter an oversized sweater from Quince. In the evening when I’m looking for comfort without buttons, lace or elastic to lounge or sleep in I grab an oversized men’s tee shirt and as soon as I put it on, my body just says aahhhh. These days comfort is key!
Comfort feels so good!
I rarely comment but this outfit is stellar! You look fabulous. And you are right that the belt is what pulls it all together. Love the hair tucked behind one ear and those great earrings.
Thanks Kim
Looks great, Jennifer!
This post hit the nail on the head! I have several Barefoot Dreams cardigans that I ALWAYS wear to any medical appointment, routine Dr appts, dentist, mammogram, etc. It’s my security blanket and a sensory pleasure when wrapped around myself! And medical offices are usually on the cooler side, so the warmth is appreciated! I am glad I’m not the only one who sometimes chooses comfort over fashion, but the BFD cardis are also very stylish!
Rest assured you’re not alone choosing comfort.
Interesting post. I changed my shirt 3 times this morning. Finally settling on a loose fitting gauze tee. I’d been up since 3 a.m. when my cat captured a mouse and brought to the bathtub to “play”. Comfort was what I need today. And I have noticed that my choice of colors is often dictated by my mood. Hope you feel better soon.
That sounds like a rude awakening 🤣 I changed my top three times before this one clicked.
I have a specific piece, but it’s one I leave off. A bra. Granted I am not well endowed so I can do this. I have extremely sensitive skin and every single bra I have ever tried irritates me at times. From the highest priced to the cheapies. If I can leave that off, I am very much happier and less irritated by the world. A 100% cotton or silk tank top under clothes is fine by me..
You are lucky to be able to forgo a bra.
You look lovely!
Thank you!
Jennifer, you look fantastic in this outfit. Classically chic!
I truly hope you feel better soon. Aching bones is definitely not pleasant.
You look fantastic in the skirt and top. Simple but oh so stylish. Sorry to hear about you feeling poorly. May I ask what osteo meds you take? My endocrinologist wants me to start taking them but I never so reluctant due to side effects. Hope you feel on the mend soon
I’m on Teriparatide which I inject daily. It’s certainly not for sissies but it’s a medication that actually builds bone density, not just prevent more loss. I’ll have to go on one of those after to maintain any bone I’ve built.
Thank you That is the same drug the Endo wants to put me on for the reasons you describe. She then said after that finishes, it would be Prolia. It is the latter drug I refuse to use due to the fact you probably have to be on it forever. It is depressing when doctors dismiss the side effects that affect people using osteo drugs when there are too many complaints about them.
The photo of you is wonderful, stylish yet understated. If you feel unwell, your smile, perfect haircut, and the look you put together are fooling the world. I responded recently to the post you did about buying the lemony-limey tank top even though it’s not “your color”. This has been a difficult year for me, aging has caught up with hubby and me. Many doc appointments but (knock wood) nothing dire thus far. But it’s like whack-a-mole: new issues crop up before the last one can be resolved. So I decided I was only going to wear “happy” cuts and colors this summer. More frivolity and joy as I hope to regain a sense of normalcy.
That’s how our health feels lately too! Perfect description. I’m going for as much joy as possible these day and dressing is a powerful tool.
I have fibromyalgia, so soft & not rigid feeling clothing is my norm. The softest cotton dresses, bamboo pants with stretch waistlines & Hawaiian Rip Skirts that are so forgiving with their velcro attachments. Sandra
I’m so sorry to hear that Sandra. I’ve read that it’s very painful.
Put that outfit on repeat rotation! THE best look, including your shorter haircut. So flattering.
Thanks Shelly
Jennifer,
Great outfit, you look amazing! I hope you feel better soon.
I have a question that is totally off topic though, have you tried the Athletica “All Ways Bootcut Pant”? I was wondering how it differs from the Endless Pant?
Thanks!
I have not but it sounds like I should.
Feel better soon! Gathered skirt, tee, and sandals today. And it feels soft, comfy, and you look great in yours!
Hi, Jennifer. Is this a new silhuette for you? If so, keep it up! It is very flattering. I especially like the way the belt makes your waist look so tiny and keeps the outfit grounded. I bet you could wear any color top with this skirt and get loads of different looks. Great job and hope you feel better soon.
Totally new for me 😊
I took Alendronate for 4 yrs. While it did improve my bone density, I did have a few side effects (acid reflux and a mild esophagus issue). I stopped taking it 2 yrs ago. My endocrinologist wanted me to have a Reclast infusion last summer, but after researching it I decided not to. My latest bone density scan showed that my density has fortunately remained the same ( It improved to borderline osteopenia/osteoporosis) for the past 2 yrs. My spine is ok, but my hips have deteriorated a bit. I am seeking a 2nd opinion with a Dr. that actually specializes in osteoporosis at a top medical school in my area. It took me 10 months to get in. I am curious to see what he will recommend. Good luck with your journey.
Please keep me posted on what you learn. Good luck.
Jennifer, you look wonderful,,,I really never thought of the idea of dressing this way. I just have a uniform, t-shirt, jeans, tennis shoes..earrings, a few bracelets and a watch…but understated casual is my go – to. The outfit on you is gorgeous, I wish I could look as good. Hope you are feeling better, and the medication doesn’t keep you feeling like a truck ran over you
Thanks Nancy
Jennifer, you look darling in your skirt outfit! It’s so fresh and fun! Perfect for summer!
You look positively amazing in that outfit. Love the contrast on you. You look comfortable AND polished. More like this please!
It’s felt wonderful too. Just what I needed that day.
This looks fabulous on you. Not overly done but knocks it out of the park. I wish I had the same ability to pull things together as you do!
Hi Jennifer. I am not “that person” who gives people suggestions about their health, because I’m not a health care professional, but have you tried using a vibration plate consistently? My husband and I both swear by ours. Lots of women have reported better bone density after using it. The benefits I’ve received are better balance/stronger core, relief from the neuropathy in my feet and better circulation overall. It also really helps my aches and pains from everyday life – especially my back and neck after I’ve picked up/played with my very heavy grandson and worked my part-time boutique job where I’m on my feet on a concrete floor for 7 hours a day. My husband says it really helps his bad knee. Anyways, I’m not expecting you to post my comment I just wanted to offer a possible solution because a lot of things hurt after 60! By the way, we have the $199 LifePro from Amazon. The reviews are awesome.
I’m so glad you mentioned it. I’ll ask my doctor about it and do some more reading. Thank you!
I hear ya! I am so tired of tucking my top into every outfit, that I am now looking for tops that I can leave out and still give me the same effect of a waist. Even though I am 5’1, I am trying to make my long tops look shorter with some tricks I have learned. Comfort is the key and makes me feel better all around. Thank you Jen for validating this.
You look beautiful and elegant in this outfit! Hope you are feeling better soon!
Thanks Tracy.
Jennifer, you look comfortable, put together & fresh in that skirt & sweater. Love the whole look on you. Also love your hair in this photo! This outfit makes it look like you didn’t have to think too hard, like it was just chosen naturally.
Hopefully you feel not so achy soon. That is probably the worst. Great advise and so true on dressing.
Thank you!!! In heat, unless I want to be dangerously irritable I must find outfits that feel like I am wearing nothing. Fresh Produce 100% cotton dresses, tops and capris are my go to. Floral Talbots 100% cotton long sleeve blouses look crisp and the thin cotton breaths and protects my skin.
Good morning, Jennifer!
J.Jill has a red and white striped pullover very similar to the Patrick one you posted if you are still looking to replace your damaged one!
Thanks Gerri, I will look!
Wow! Something I have never thought of. I’m well into my fourth quarter as Johnathan Winters used to say, and never considered this idea. Thank you and I am definitely going to add this to my morning ritual.
Johnathan Winter was hilarious. I adored his humor.
What are the style words?
We discussed the style words here.
Smashing outfit! You look contemporary, comfortable and cool. Love the contrasting tones on you. Good luck with the meds – sometimes adjusting or substituting ends up being required.
She did mention switching meds so we’ll see. I’ve got another 18 months to go on this one which might be intolerable
What an interesting post, thank you. I have a deep phobia of dentists, and when I have an appointment, I wear the same thing — a midi length black tee shirt dress (EF) that I know will feel 1) soft on my legs and 2) loose at my waist while sitting in the dental chair, and some kind of soft cotton sweater/sweatshirt/cardigan to pull around me like Linus’ security blanket. I also wear my favorite silver loafers that I enjoy seeing while sitting there, LOL.
Perfection!! I can see why that’s perfect.
Absolutely adorable outfit. And you look soft and feminine!
I dress according to how I feel every day. Color is my main drive. It has to match my mood. Some time’s if I plan an outfit in advance and I put it on if it doesn’t make me happy off it go’s and on to another! Very honestly it make’s me crazy sometimes and my closet is overflowing with clothes. Also, everything has to match in one way or another. I worked for an airline most of my life and had to wear a uniform…that may have something to do with it! BTW you look wonderful in this outfit, it’s my favorite on you! Hope you feel better soon.
I have a slight passion for matching too!
Adorable outfit! So chic that you could wear it anywhere! Elegant and classy! Bravo for us aging beauties!
What an interesting post! It makes so much sense, really, to check in to what we need rather than what we think we “should” wear.
Your outfit is absolutely lovely. Love the mix of brown and white!
Jennifer,
I rarely comment but you look the best ever in this picture. Outfit, hair, the whole thing.
You’re so kind, thanks Judy
Maybe I need softness today too because I really enjoyed just seeing your outfit today. I tend to reach for midi/maxi length linen or soft cotton dresses when I need extra comfort, but I forget about my skirts! Good reminder
I’m loving skirts more and more.
So true!
I would be interested to know if your symptoms are a side effect off the osteoporosis meds as I am starting mine this week..always good to know possible side effects.
One doctor thinks yes, one thinks no. My guess is yes.
Jennifer, your outfit is fabulous. You look amazing – nobody would know you were in pain. Best wishes to have the issue remedied.
Thank you Yvonne. xo