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What I Learned from Weekly Outfit Planning

May 7, 2024

Do you ever struggle to get dressed for your day? I sure do. Some days I just lack the motivation even to get out of my pajamas or workout clothes. Other days I stand in my closet and feel overwhelmed as I look at the assortment in front of me. I find myself wearing the same things over and over…or I put together outfits that don’t really feel like me. And sometimes I don’t feel motivated to complete an outfit because I’m tired and lack the creativity at the moment. That’s why I decided to try weekly outfit planning. And here’s what I’ve learned.

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I’ve been planning out my daily outfits on a weekly basis for just a few weeks now. But I’ve already learned that this is indeed a good practice for me. Each weekend I’ve given myself until Sunday afternoon to have pulled together daily outfits for the upcoming week.

my garment rack with display shelves

I’ve been using this Weekly Outfit Planner from our Subscribers’ Printable Library. (I’d love to give you access to this guide and the other MANY resources I have in the Printable Library. You simply need to be an email subscriber to my daily OR weekly email. The password to the library is always at the bottom of the most recent emails I’ve sent, and it does occasionally change. I upload new resources EVERY month.)

DFMD Weekly Outfit Planning Guide

I’ve actually updated the printable Weekly Outfit Planner with some new features since taking that photo. It now has space to write out your “style goals” and any “styling notes” for each day. More on that later.

So below I’m showing you my daily outfits for this past week while I also share a few lessons I’ve learned from weekly outfit planning. You can shop the looks, if you’d like, through the links in the captions below the photos. But in the text I’m going to focus on sharing my take-away from this new project.

Lesson 1 & Monday’s Outfit

A few days into the first week I realized that it’s best to plan your weekly outfits in a way that fits your lifestyle. I had planned out an outfit for each specific day. But as a woman who works for herself at home, my days are varied, so I don’t necessarily know what each day will bring at the beginning of the week.

button front tank // wide crop pants // sandal // shoulder bag // pebble necklace // herringbone necklace // earrings

I don’t go to a school or store or corporate office each day. So I can give myself a little more wiggle room. Rather than planning out an outfit for each day, I’m now simply planning five workday outfits, one Saturday outfit and something to wear to church on Sundays. I let myself wear those five workday outfits any day I want. Allowing myself some flexibility makes this weekly habit more enjoyable and workable.

Lesson 2 & Tuesday’s Outfit

I learned from weekly outfit planning that I’m more prone to wear a wider assortment from my closet if I plan my outfits for the whole week at once. If I wait until “the day” to choose my clothes and put together an outfit, I tend to pick the first thing I see or that grabs my attention.

shirt (also available here) // lantern pants (more economical option here) // mules (more economical option) // crossbody bag // earrings // necklace

As someone who invests in high quality clothing for her wardrobe, I want to make sure I’m wearing those pieces. Planning ahead prompts me to reach for things I might not gravitate to on the fly. For instance, I purchased those Gucci mules for my birthday over a year ago, but I haven’t worn them nearly enough to justify the cost. Ivory mules and loafers are very in style right now, so this is definitely the time to wear them. Planning my outfits ahead reminds me to incorporate pieces like these into my looks.

Lesson 3 & Wednesday’s Outfit

I’m more prone to wear more color if I use weekly outfit planning. For years I’ve been sharing my daily outfits in my Friday How I Really Dressed for My Day posts. And quite frequently in those I’ve caught myself wearing neutrals all week. Or maybe I’ve worn color once or twice during those weeks.

linen button up // tank is old (similar option) // jeans // sandals // necklace // earrings // bracelet

But since I’ve been using weekly outfit planning, I’ve encouraged (not forced) myself to incorporate multiple colors into the week’s lineup. This particular week I think I wore – or at least planned to wear – four different colors. That’s pretty colorful for me! And I wore a variety of neutrals, too.

Lesson 4 & Thursday’s Outfit

I’ve learned that I’m more prone to wear a variety of fabrics and styles when I schedule my outfits a week at a time. If I’m not mindful, I’m prone to wear linen, linen, linen in the summer. I guess there’s nothing wrong with that. Except most of my linen pants and dresses are very forgiving in the waist. Ahem. For the sake of maintaining my weight and figure I need to wear a structured waistband more often than not. Anybody else???

POETRY sweater // lantern pants (more economical option here // sandals (use code Kay20 for 20% off at Easy Spirit // pebble necklace // herringbone necklace // earrings

As much as I love my Eileen Fisher lantern pants, I just can’t allow myself to wear these elasticized waistband pants daily. Ha! Planning ahead helps me avoid pitfalls like that one. Do you have similar habits you have to be careful about?

Lesson 5 & Thursday Evening’s Outfit

I’m more likely to accessorize thoughtfully and well when I plan my outfits ahead for the week. When I try to get dressed for my day without any planning, I find myself scurrying around at the last minute looking for a belt or just the right necklace or a handbag that works with my shoes. Anybody else? So even if I do manage to accessorize well, it’s often at the cost of being late walking out the door or at least feeling frazzled when I finally do get my look together.

dress // belt // sandals // purse // pebble necklace // herringbone necklace // earrings

But when I planned ahead recently, it was a pure joy to put on the outfits I’d planned for each day. Getting dressed was fun instead of frazzling. And I just didn’t even have to think about pulling my outfit together, because I’d already done that on a Sunday afternoon when I was feeling more creative and relaxed. For instance, I had already taken off the fabric belt that came with the dress above (new favorite, by the way!) and tried it with about six different ones. In the end I knew that this thinner leather belt was the ONE that worked perfectly with it. So when I needed to change clothes quickly Thursday afternoon to head out for an evening appointment, I was able to pull together this look with no thought.

Lesson 6 & Friday’s Outfit

From weekly outfit planning I’ve learned that every day is worthy of a planned outfit. I knew that I’d be working all day at my desk on Friday and going nowhere. But I work more productively and feel better if I get dressed for my day. So I think it’s smart to plan an outfit even for very casual, relaxed days at home.

linen button up (similar option) // jeans // retro sneakers (more economical option)

If you’re having a garage sale, plan an outfit. If you’re cleaning out the basement, plan an outfit that works for that. If you’re going hiking, plan an outfit. We have to put clothes on each day; we feel better and find it easier to do that if we plan ahead.

Lesson 7 & Sunday’s Outfit

I don’t have an outfit to show you for Saturday because we taped videos all day and I never settled into an outfit to speak of. So, yes, that meant that the outfit I’d planned for Saturday never got worn. Actually that turned out to be a blessing because I was able to just move it to the next week.

dress (TTS) // heeled sandals (TTS) // bag no longer available // bracelets // Arabella diamond chain necklace (c/o) // Maya hoop earrings (c/o) (Use code KAY20 at Penelope Jewelry for 20% off)

The final lesson I wanted to share is that I learned that knowing my style goals for each day is even more important than taking into consideration the weather. Obviously I looked at the weather app and planned accordingly for each week. But keeping in mind my style goals helped me to know what type of outfit to put together. Some style goals that I consider are:

  • being comfortable (for working at my desk all day or travel)
  • being able to move easily (for hiking or travel or house keeping)
  • looking chic and stylish (for work appointments, special occasions, etc.)
  • looking modern (for speaking engagements and other events, or just daily)
  • looking approachable and relatable (for speaking engagements and meet & greets)
  • looking a little edgy (because I just want to, ha!)
  • feeling confident (for work or appointments or speaking engagements, etc.)
  • looking my most figure flattering (for a special date night or event)
  • feeling feminine and pretty
  • feeling cool or warm
my garment rack with display shelves // other rolling rack options

I’ve discovered that no one outfit can accomplish all of those style goals. You have to prioritize for each day. And when I plan my outfits ahead weekly, I’m more likely to take the time to think through the style goals I want to achieve for that day or event or appointment. And then I can put together an outfit accordingly. Bottom line? Weekly outfit planning results in fewer regrets later on.

So those are my thoughts on weekly outfit planning. I’m sold. I’ve cleared off the space in my office where I used to stage outfits for the blog, and now I’m using this hanging rack for my weekly outfit planning instead. I decided if I’m going to be Dressed for My Day I better focus a little more on getting dressed for my days. Ha!

Don’t forget, you can get a revised, printable PDF of my Weekly Outfit Planner in the Subscribers’ Printable Library if you’re a subscriber. Not a subscriber? Take care of that below. Have a great day! Oh, and I’d love to hear your thoughts on weekly outfit planning in the comments below. Just click on JOIN THE CONVERSATION.

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Blessed for My Day

I’m not sure there are many things that feel worse to me than being misunderstood. Especially when it is someone you love dearly and whose opinion you value, it is heart-wrenching to feel like they have misjudged your motives or read something into your words that you did not intend. Can you relate to that? I suppose we all experience misunderstandings at times. And some of those seem to take on a life of their own and become divisive and even relationship-breaking.

But we can trust that even when family or friends misunderstand us, God knows our hearts. Of course that can be a little sobering, too. But it reminds me that keeping a clean heart before the Lord is to be my priority. Yes, relationships with other people are important and dear. But in the end, I must stand right before the Lord and trust that He will, in His time and best judgment, bring mending to those relationships if that’s best for me.

Now Eliab his oldest brother heard him when he spoke to the men; and Eliab’s anger burned against David and he said, “Why is it that you have come down? And with whom have you left those few sheep in the wilderness? I myself know your insolence and the wickedness of your heart; for you have come down in order to see the battle.” But David said, “What have I done now? Was it not just a question?”  ~ 1 Samuel 17:28-29

xoxo, Kay
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15 thoughts on “What I Learned from Weekly Outfit Planning

  1. My friends tease me about being so organized, so of course this idea really resonates with me! I always plan in detail what I will take on a trip, but hadn’t thought about doing it for a week at a time when at home. Interesting!

  2. When I worked in the corporate world, I always planned my weekly outfits on the weekend. Since I retired, I have continued that practice and find that, as you stated, it helps me make better choices and utilize more of my wardrobe. Thanks for all you do, Kay!

    1. Great idea ladies! I’ve been planning ahead one day at a time before I retire for the evening and that works great but I’m going to plan a few more days ahead. I think you are all right…. I’ll vary my dressing, it will be easier and more efficient too.

  3. Kay! You are a woman after my own heart with your planning and organizing your outfits for the week! I really find joy and creativity in doing that, especially for special events. Sometimes I will plan several days ahead and will tweak it for days, until I drive myself crazy. So, I need to know when to stop! HAHA! I love your list at the end of reasons to plan an outfit. I would add one…To be comforted and cozy for a health appointment. I always wear a comfy pair of soft joggers and a Barefoot Dreams cardigan or pullover for those mammograms, dentist appointments or to donate blood. It really does make me feel better! HAHA!!! Pray you and James have a great vacation in Alaska.

  4. This is a great idea! I have hear of other people doing this but thought it would be soo overwhelming to do. But, you have inspired me to give it a try! All your outfits turned out great and now looking forward to the challenge. Maybe it will help me see what I am missing from closet. Thanks Kay!

  5. Loved that you planned your outfits for the week. When I taught middle school students, I always wrote down on my calendar what I wore to school each day. Not necessarily to be stylish, but because I would forget what I wore day to day. I didn’t want to students to think “she wore that outfit a few days ago!” They definitely would remember better than I could!

  6. I use this method for special occasions, rather than every day work outfits. My work wardrobe is pretty much a mix-n-match, grab and go setup – all my tops coordinate with all my bottoms, so I just pick whatever strikes my fancy that morning and head out the door. But when it comes to dressing for something special, I plan that very purposefully. I will lay those outfits out the night before so every component is there and ready for me the next morning.

    I do wear pretty much everything in my wardrobe on a routine basis. But one thing that I forget about is to rotate through my jewelry. So every once in a while, I like to look through all my jewelry to see if there’s a piece I haven’t worn in a while. If so, I’ll set it in a prominent place so I can wear it the next day. 🙂

  7. Thank you for continuing to send me your posts. I think I understand a pastor’s wife’s life a lot. Have been a good friend to a missionary wife for a lot of years. And now am a good friend to our new pastor and his wife. still in Japan. You see things, hear things, right? My mom died this week, God is giving me the opportunity to help my sister. She is there, in the States.
    I understand her need to talk and talk, not just about my mom-we are bouncing from subject to subject. God gives us specific things to do at diff. times. God bless you. Praise God, for dying on the cross for us. Cathy Ogi

    1. I’m so sorry to hear about the passing of your mom, Cathy. May God grant you and your sister peace and comfort during this time.

  8. This is such a timely post! I’ve spent lots of time getting rid of what I don’t wear and keeping things I like. I’m very happy with my current wardrobe. I have so many cute clothes I never wear because it seems I dawdle and then when it’s time to put myself together to go out of the house I just throw something on without much thought. I look fine but not really how I’d like to. I am definitely going to try this method so that I can enjoy more of the clothes I have and love.

  9. When I worked I did week outfit planning every Sunday night. I hung everything together for the week even all my accessories. I did this for years. I didn’t realize it was an unusual thing to do. I started doing it years ago because I had a hard time getting up at 6 and getting it all together that early in the morning. I was a school teacher before I retired and I felt it necessary to be well pulled together for my day. I used the same formula that you use, pants (or skirt), top, completer piece , shoes and accessories. I love scarves and have a drawer full. They were one of my favorite accessories to use. So glad this plan is working out for you. I loved it but rarely do it now since I am retired and don’t have to make those decisions at 6 in the morning!

  10. I love this! I noticed I wasn’t using all my purses, I don’t like switching purses so I decided to pick a purse for the week and make outfits that go with it. Of course I took into account the other things-weather, what I’m doing…. My first week went well. I love planning! Thanks for the idea!

  11. I used to plan my wardrobe for the week when I worked. Since I retired I only plan my outfits for going to church on Sunday and if I have something special to do. I plan by the weather since it changes so much in Texas. In the summer I do get in a rut because it’s so hot. I’m going to try more week planning. I wish I had room for a rack like yours.

  12. Planning for the week would make my days easier rather than standing and looking at my closet and would help me pull in more items rather than just the few ones I tend to pull over and over. Now where do I find the password into the printable library?