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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?

Personal stylist Jennifer wearing a white balloon skirt outfit as an example of dressing for how you need to feel.
OUTFIT DETAILS HERE

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.

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95 Comments

  1. Melanie Toppe says:

    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.

  2. 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!

  3. 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.

    1. 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.

  4. Linda Land says:

    I love that outfit on you! So chic and it also looks comfortable. Thanks for the inspiration!

  5. 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!

    1. That is amazing Cherie and gives me hope. Thanks so mucg for sharing!!

  6. 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…

    1. I am in the same camp as you about shoes!!

  7. 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.

  8. You look fabulous. The recent haircut fits you well.

  9. Lynnefred says:

    I really like this outfit on you. You look stylish, modern and youthful. Very nice!!!

  10. Sue Larson says:

    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!

  11. Susan in the 'burbs says:

    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.

  12. 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.

  13. Mary Packnick says:

    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

    1. I’m on Teraparatide injections daily.

  14. 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.

  15. 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.

  16. Elizabeth L says:

    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!

  17. Christine Arquilla says:

    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.

    1. I adore the sound of your outfit!!

  18. 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

    1. 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 😉