Cool Weather Wardrobe Planning – Part Two

In my last post, I outlined a six step process for planning and putting together a seasonal wardrobe.   The first four steps of this process should be done before you ever set foot in any brick-and-mortar shop or enter an e-commerce store.  If you take the time to do some planning before buying anything new, you’ll have a much better chance of making the right choices and being happy with what you purchase.   In addition, your wardrobe will be more workable for your actual lifestyle rather than for a past, fantasy, or hypothetical one.

Since the seasons are transitioning from warm to cool where I live (we really only get two seasons here – summer and “not summer”), I thought this would be the perfect time for me to put my method to the test with my own wardrobe.  So over the course of the past few days, I went through steps one through four.  In today’s post, I will recap my process and share what I learned and my plans for moving forward with my cool weather wardrobe.

My New Jeans "Uniform"

These outfits are typical of what I wear during the “cool” weather season…

Preliminary Step – Closing Out the Current Season

Before I started going through my cool weather wardrobe, I took some time to review my summer clothing, as that’s what I have been wearing for a number of months and it’s fresh on my mind.  I highly recommend that you take this step at the close of each season.   It’s much easier to perceive what has and hasn’t been working for you when you’re looking at your recently worn garments and accessories.  I will likely explore this in greater detail in a future post, but for now I will summarize what I learned.

What I’ve been wearing most often are dresses (both knee-length and maxis) and maxi-skirts.  I still like knee-length skirts, but I have phased out many of my old ones because I now prefer a shorter length with a less flared cut (which has been surprisingly hard for me to find when shopping).  In terms of tops, I have almost exclusively been wearing tank tops, mostly in a ribbed cotton style.  I haven’t had much need for toppers due to a very hot summer, but when I have worn them, my favorite silhouettes have been tie-waist and cropped cardigans.   I no longer favor the knit blazers that used to be my wardrobe mainstays, but I still have a few that I like.  In terms of shoes, I’ve mostly worn two pairs of flat sandals with my maxis and a few pairs of wedge sandals with my knee-length dresses and skirts.

2015 Summer Ensembles 5-8

This is basically how I’ve been dressing the past few months… 

I will cover what I’ve decided to pass on in a future post, but here’s a list of what I would like to add to my warm weather wardrobe for next season (some of these items are crossover pieces that can be worn in cooler weather, too):

  1. Bright-colored knee-length skirt
  2. Bright-colored cropped jacket, perhaps in a moto style (preferably in either cobalt or burgundy)
  3. Short-sleeved tops to wear with skirts (2)
  4. Black cropped/Capri pants (narrower cut, possibly the “metro slouch” style from Athleta)
  5. Bright or patterned sandals (to replace existing red shoes – heel is a bit too high)

That’s all I could come up with, as I am pretty “set” in terms of warm weather clothing and shoes.  One benefit in creating this list now is that I may find some of these items much sooner than next summer.  Since I live in a temperate climate with quite a few unseasonably warm days throughout the year, it’s not a bad idea to buy some things off-season.  Plus, I can see wearing some of the pieces listed during the cooler season as well since the temperature differential is not that high here.  This may not be the case for many of you, particularly those who live in places with very distinct seasons.

I usually don’t advise buying clothing that we’re not going to wear for many months, especially for those of us who are still honing our personal style.   But for those who are very clear about what they need, love, and wear, it’s not quite so risky.   For most people, a list like what I made above will be set aside and reviewed again as the season approaches, at which time some changes may be made.   It’s still a good idea to make the list now, even if you’re not going to shop for those pieces for a long time.

Step One – The Closet Review

Step one in my seasonal wardrobe planning process is to review your existing wardrobe for the coming season.   This involves taking out all of the items for that season, going through them, and trying them on.   The reason for the try on is to make sure your clothes still fit your body and suit your lifestyle and desired style aesthetic.   Doing this can also help you determine which pieces need to be tailored so you have time to take care of that before the season begins in earnest.

I will cover what I’ve opted to cull from my cool weather wardrobe in a future post.   However, I will say now that it’s really not much.  I’m still happy with most of what I have for the “not summer” season, which is roughly two-thirds of the year.  I don’t have anything that needs to be tailored, either, as I typically take care of those needs as they are identified throughout the year.

Another part of this step is to switch out seasonal clothing and rearrange your closet as needed for the coming season.  As I don’t store my off-season clothing outside of my main closet, I don’t have much to do here.  I will likely move things around a bit and place my cool weather clothes and shoes more front and center, but I opted not to do that just yet.  I can easily see and find everything in my closet now, so when the cooler weather arrives, getting dressed will be simple and straightforward.

Step Two – The Powerful Questions

The second step is to answer a few powerful questions related to the coming season’s wardrobe. Here are my answers to those questions:

What wardrobe gaps, if any, did I notice?

To answer this question, I consulted my outfit journals from the last cool weather season.  To make things easier for myself, I kept a running list of items I found myself wanting in answer to the “What would I change?” question in each journal entry.  Here’s what I came up with:

  • Pants that are not black or denim
  • Black straight-leg pants – perhaps ponte knit, like leggings but not so body-hugging.
  • Black “athleisure” pants – I have a particular pair in mind that I’ve wanted for months. They will be perfect for my casual lifestyle but are more “polished” than my workout pants.
  • Bright-colored or print tunic
  • Denim skirt

I also answered this question in terms of my at-home wardrobe and identified these two gaps:

  • Workout shorts – mostly worn for doing cardio at home
  • Long-sleeved pajama top

What items in my closet need to be replaced soon?

It’s important to remember that just because something is getting worn out, it doesn’t necessarily need to be replaced.   As I looked through my closet, I made sure to ask myself which items I would truly miss if I didn’t replace them.   I ended up with just this short list of replacement needs:

  • Black ankle boots – I currently have three pairs, two of which are very worn out and one that I don’t like all that much. I would like to replace them all with one new and really fabulous pair.
  • Printed shoesTo replace my very worn out leopard print flats. I will likely buy another pair of leopard print flats, but I want to be open to other prints as well.
  • Black low-heeled peep-toe shoes The ones I have are not very comfortable, but I continue to wear them, as they are the best option for some of my outfits. I want to find a better alternative.
  • Black lightweight coat Some say I have too many coats for living in San Diego (and they’re probably right), but I do feel the cold more than most and I have worn my current black coat many, many times. I would miss it if I passed it on, but it is looking “tired” and needs to be replaced. Black is my key neutral, so I know the coat will be worn frequently.

I also identified a few replacement needs in my at-home / workout wardrobe:

  • Lounge pantsreplace existing black and grey pairs (hard to find because I need talls and prefer a somewhat looser style that what is prevalent in stores).
  • Short-sleeved pajama topsI usually just wear loose V-neck t-shirts with my pajama pants, but the ones I have are very pilled and worn out.
  • Baseball cap This would seem to be an easy item to find, but I like a particular style and haven’t been able to locate any such hats. The one I wear on my walks is ten years old now and quite “tired”! I may also want to replace the visor I wear on warmer days, but that is a less urgent need.

In what ways do I want to update or modernize my wardrobe (trends, new silhouettes, etc.)?

I am more of a classic dresser, but I do pay some attention to trends to see if there is something new I’d like to try with my wardrobe.   I always like to shop my closet first to see if I can use something I already own to adopt a new style, but sometimes it’s necessary to buy a few new things in order to modernize my wardrobe.   I did quite a bit of this last year, especially in terms of my pants (slimmer) and skirts (mostly maxi lengths).   Here are the things I would like to buy to update my closet this fall/winter:

  • Asymmetrical top
  • Burgundy itemsI have a few already, but I would like to add another top/topper and a bottom while this key color from my palette is plentiful in the stores.
  • Bright-colored purseEither burgundy or cobalt

Step Three – The Shopping List

So if I put all of the items above into a single list, I come up with the following.  To make more sense of things, I have divided the list into tops/toppers, bottoms, shoes/accessories, and at-home/workout needs.  Note that this list is not in any particular order in terms of priorities. I will take care of that in the next step.

Tops / Toppers:

  • Bright colored or print tunic
  • Black lightweight coat
  • Asymmetrical top
  • Burgundy top or topper


  • Pants that are not black or denim
  • Black straight-leg pants
  • Black “athleisure” pants
  • Denim skirt
  • Burgundy pants or skirt

Shoes / Accessories:

  • Black ankle boots
  • Printed shoes
  • Black low-heeled peep-toe shoes
  • Bright colored bag

At Home / Workout Items:

  • Workout shorts
  • Long-sleeved pajama top
  • Lounge pants (2)
  • Short-sleeved pajama tops (2)
  • Baseball cap

Seeing everything laid out like it is above makes my cool weather shopping list a lot clearer.  I can see that I have 18 items on my list (20 total items since two things on the list call for duplicates).   That may seem like a lot to some of you, but it is actually far less than I have bought this year (as of September 30th, I have added 78 items to my wardrobe this year, including jewelry).

This planning has already been extremely helpful, but there is one final step remaining that will really get me on the right track with my cool weather wardrobe shopping.

Step Four – The Prioritization

As I mentioned in my last two posts (here and here), I don’t have much of my 2015 clothing budget remaining due to overshopping during the past few months and earlier in the year.  There is no possible way that I can buy all of the 20 items outlined above over the course of the next two-plus months.   Many of my cool weather purchases will need to be made in the early months of 2016.  By that time, we will already be well into the cooler season, so I need to prioritize what I should buy first.

The way I’ve decided to do this is to divide the 20 items on my list among the next four months (I’m counting the remainder of October with November).   These allocations are not set in stone and I may opt to make some revisions down the line, but it’s a good starting point.  I need something to go on as I get started with my cool weather shopping. I’m going to review my list each month and see if there are any substitutions or omissions I’d like to make.   I will update you on my list with each accountability update and I may include the list on the website somewhere.

Here is how I see my shopping unfolding in the coming months.  The lists for October/November and December may need to be cut down, as I have only a little over three hundred dollars of my budget remaining for the year. However, I included more items for December, as I may ask for a few items on my list as Christmas presents.


  • Black “athleisure” pants
  • Black low-heeled peeptoe shoes
  • Short-sleeved pajama tops (2)

December (some of these may be Christmas presents):

  • Lounge pants (2)
  • Black straight-leg pants
  • Asymmetrical top
  • Black lightweight coat
  • One burgundy item (either top/topper or bottoms)


  • Black ankle boots
  • Printed shoes
  • Pants that are not either black or denim
  • One burgundy item (either top/topper or bottoms)


  • Bright colored bag
  • Long-sleeved pajama top
  • Denim skirt
  • Baseball cap
  • Bright colored or print tunic

This was actually pretty difficult for me to do.   I found myself really wanting to buy all of the items on my list as soon as possible, but that’s just not going to happen given my current budget.   I opted to get the black “athleisure” pants in October/November because they’re something I have wanted for quite some time.  Also, the black low-heeled peep-toe shoes made the early cut because the ones I have are both uncomfortable and pretty worn out.   I don’t want to continue wearing them (they are the best shoes for a few pairs of pants) when they hurt my feet and don’t look very good.   The pajama tops are really necessary, as the ones I have are quite pilled and replacements are long overdue!

The December list may well be too long and some items may have to be pushed out to January.   If I can only buy one item that I have allocated for December, it will be the lounge pants, as I wear them often and my existing pairs are getting quite worn out.   The black pants (preferably ponte knit) are next on that list.  I can easily get by without them, but I do see myself wearing such an item often once the temperatures dip down a bit here.   The other items can either be Christmas presents (my husband often wonders what to get for me) or early 2016 purchases.

If I happen to find items that are slated for later months earlier in the season, I will move some things around.  The priorities above are not meant to be set in stone, but they are good guidelines for me to go on so that my shopping is more deliberate (still working on that theme for 2015 and this process is part of that…).    Flexibility is important, especially since we aren’t always able to find what we’re looking for. Still, it’s helpful to have some structure for our buying so we don’t fall prey to all of the clever marketing (see here for some examples) that’s meant to distract us and have us whipping out our credit cards at every turn.

Conclusion and Your Thoughts?

I’m so glad I opted to put my new seasonal planning process to the test!   I feel the steps worked well for me and helped me gain clarity on what I need for the coming season and what will best serve me.   Yes, this process takes some time (perhaps two evenings or one weekend day, for most people) and there is a bit of redundancy between steps two and three, but I feel it was well worth my time to do it.   I believe my upcoming shopping will be far more targeted and I’ll end up with a wardrobe that’s a better fit for my life.

I hope that reading about my experience with the process was helpful. Now I’d love to hear from you.  If you’ve taken the time to do the seasonal wardrobe review, please weigh in. Some of you already have done so in response to my last post, but I welcome additional feedback or questions.

Before You Go…

  • Podcast Appearance:  I recently appeared on the “Inner Effort” podcast to discuss how to manage compulsive shopping. Of course, I don’t have all the answers on this topic, but I enjoyed a lively discussion with the show’s host, Alen Standish, about the emotions that drive the need to shop, how I feel when shopping, and some tools and techniques we can use to help ourselves when the urges to shop come on strong.    Here’s the direct link to my episode of the show.  If you’ve ever wondered what I sound like, now you can find out!    You can also find links to podcasts I’ve appeared on, interviews I’ve done, and articles I’ve written for other blogs over at my “As Seen In” page.

18 thoughts on “Cool Weather Wardrobe Planning – Part Two

  1. Another great article with meticulous detail. It’s a rather unique experience but I’m actually very happy with my cold weather wardrobe. I have a capsule of quality items from last winter where I defined my style & bought with intention, instead of the usual scatter gun approach. At the beginning of this winter I identified the gaps (camel knee length boots & knee length black cardigan) & have purchased good quality versions. I found buying higher quality meant I only bought once instead of several lower priced options. I’m also getting better at shopping for my real life (housewife) rather than the fantasy (rich fashionista!). I had a wardrobe full of dressy items & no casual clothing. I’ve started wearing my nicer items around the house (fur gilets,ponchos & I found by removing the Spanx slip from several LBD’s they were transformed into tunics that could be won with leggings around the house). I think shopping with intention removes the guilt & restores my former joy of shopping. Thanks for the continuing inspiration x

    • Glad you liked the article, Sharon! How great that you are happy with your cold weather wardrobe and only really needed two new things to get it in shape for this year. You’re right that buying higher quality often means you only need to buy ONCE instead of several times. I have had the experience of having to buy several things more times than I can count, and I also used to buy for a rich fashionista’s life rather than my own. You have been very creative with re-purposing your items to wear at home! I would have never thought about transforming LBDs into tunics.

  2. Great plan! You know I’m a fan of planning purchases, as well. My only hesitation is putting the exact month of purchase ahead of time. I have tried this approach, and it’s often better in theory than in practice. Something might come on sale at a different time, or an item appears in front of you that was slated for a later month, etc. I find thinking seasonally is more realistic with how shopping actually happens. But nothing wrong with trying to work out when we can spend what and seeing if we can’t fit our purchases into a plan.
    I might find my berry Uggs on a sale for Black Friday. That would likely put me over for this year instead of waiting the 4 weeks until my next shopping year starts. But if it’s a wiser time to buy in order to save, I’ll do just that. As an example 😉
    Best of luck with your honed plan for ‘not summer’ 😀

    • You raised a very good point about planning purchases by month, Mo. I decided to try it for this season, but I can see that my experience may be very similar to yours. We never know when we might find what we need. Mette seems to have good luck with it with her shopping calendar, but maybe it’s easier to find things in Denmark than here (or maybe she’s just better at it than I am). I am just trying to be more deliberate about my shopping and to define my key priorities. We’ll see how it all works out. I hope you find your berry Uggs at a Black Friday sale. I can see that this would be a good purchase for you and I hope you can get a deal on them!

  3. Thanks for the link to the podcast. It was great to hear your voice. It made me like you even more than I already do!

  4. The podcast was wonderful. You presented so many ideas, I swear there could be a year’s worth of interviews expanding the ideas you presented. I liked how YOU kept the topic moving forward during the program.
    You have a nice “smile” quality to your voice. It was great to hear you.

    • How kind of you to say all of this, Gayle. I’m glad my voice has a “smile” quality to it 🙂 I still need to listen to the podcast myself! I agree that I could expand the information quite a bit. My husband keeps telling me I should do YouTube videos based upon my various blog posts. This is something I hope to get going soon. I’ve never done videos before, though, so there are things to figure out…

  5. I agree that the podcast is wonderful. It was lovely to hear your voice (which sounded warm and gentle to me), and the interview was well structured and informative.
    The shopping plan looks very organised! I’m trying the 5 piece French Wardrobe idea, which means planning 5 per season (4 seasons for me). I haven’t stuck to it as well as I’d hoped (total about 30 so far, incl. accessories but excl. sportswear etc). However it has helped me be more focused, and I’ve bought fewer, better quality things as a result, so will keep going.

    • Thanks for your kind words about the podcast, Alice. I’m glad you liked it and that you felt my shopping plan is well-organized. I am considering doing the 5-piece French Wardrobe plan for next year. I don’t know if I would be able to stick with just 20 purchases, either, but I agree that having such a plan can help us to be more focused and to buy less (and better) overall. I may modify it some to make it more my own. I’m still pondering ideas…

      • I think you can adapt it any way you want. Eg I read that you shouldn’t count replacing basics – but I decided to count everything, as otherwise I might be tempted to buy loads of cheap tee shirts and ‘not count’ them, exactly what I want to avoid. For me, something like 5 garments + shoes might be more do-able than 5 total, so I will also re-think for next year. However I think it has helped to think of a planned new ‘set’ of things for each season, and to make each one special.

      • You’re right that this and all challenges are very adaptable. After all, we are the ones doing it, so it should meet our needs. I like the modification you are proposing for next year. I agree that having to plan your 5 items each season can really target shopping. Any sort of planning that we do is definitely better than NO planning. When I don’t plan at all, I often end up buying either similar pieces to what I already have or closet “orphans,” neither of which serve me.

    • This is a great article, Alicia. Thanks so much for sharing it! I will definitely include it in my next link round-up, which will go live later this week. Glad you liked this post and I hope you enjoy the podcast, too.

  6. Thank you for these planning posts and the fabulous podcast! I will be heading back into the shopping world in another week after my year off (with a couple of exceptions), and have been doing lots of planning. One thing I have found helpful in the past is to keep a running list of the purchases I want(ed) to make (even better if you date the items as added). Seeing them all on paper helps me realize how much I am wanting, and about how many of those items I have changed my mind, even after only a day or two. Like Alice above, I am thinking about the 5 Piece/French idea, in two seasons, but wonder if I will just buy too many “basics” which don’t count in the 5… Just gotta keep learning and trying new things!

    • Great to hear from you, Liz, and I’m glad you liked these posts and the podcast. Congrats on sticking with your “year without clothes shopping.” Would love to “hear” about what you learned. If you are open to doing so, it would be wonderful to feature you in my “stories of recovery” series. I’m sure others could learn a lot from your experience! I like the idea of keeping a list of “wants” and checking back in on them. I know that most of the time, I don’t even end up remembering those items. That’s why the “power pause” can be so very effective. I have the same worry about the “5-piece French Wardrobe” concept, but we can always tailor such a challenge so that it best suits our needs (i.e. limit the basics as well). I’m pondering my 2016 challenge after I finish “LIWI,” which has been very instructive for me. I think that even doing ANY challenge will stretch us, so we can’t really do it wrong.

      • Hmmmm… I’m not sure how one defines “recovery”! For me, fasting is often easier than moderating, but hopefully I have learned something this year. I suppose the proof will be in the pudding next week (and beyond) about what, if anything, I have learned! Writing would certainly be a way to help me stay honest and accountable. Please feel free to e-mail me with any details, or requirements you may have, and I’ll see what I can do!

      • I don’t think we have to be fully “recovered” to be able to have useful things to share with others. I agree that fasting is often easier than moderating for many of us, but I know you have learned a lot over this year and that others would love to read your insights. I will email you with more details and would love for you to share your story!

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