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.

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