To walk into our closet, knowing we have the elements to pull together a wardrobe that suits the occasion as well as communicates our signature style — that is often the dream, yet the approaches we take to reach it often prevent us from achieving it completely. However, this is not to say, we haven’t tried with diligence, nor that we haven’t experienced this feeling during some seasons, or during a period of our lives. 

To the latter point, when we have tasted what it feels like to know our closet supports and the life we love living and the responsibilities we must tend to, an ease is felt. It is something we give ourselves, and yet the reason we may no longer experience that ease is that we didn’t realize exactly how we attained it and thus how to maintain it.

In our new 12-part series (a new post each month of 2026), I’ll be showing you the approach I have taken, something I began intentionally back in September with three objectives guiding me:

1. Each item fills a void that exists and that I have needed or would have reached for and worn often (not necessarily year-round, but frequently during its season to shine) had it been in my closet. Nothing trendy – instead, timeless for my coloring and body shape.
2. Investment items that will last and that I love.
3. Proceed at a pace that fits my budget so that everything is paid in cash. 
   • Yet, prioritizes completion and the value of having a dependable wardrobe. Set an end date – set a timeline (12 months in our case). 

While I will share with you the specific items I have purchased, this is only to offer an example. I will shop the item and similar items each month, but the primary objective is to inspire you to look within your own closet and see what you need, and how to fill that particular void, with ideas and examples shared in the post. 

How I came up with this approach:

Since retiring from teaching in 2021, I have been consciously paying attention to how my days unfold and to the clothing items I need from season to season for the activities and work I take part in. Always wanting to look my best, but primarily because I love clothes that exude confidence without pretense, I missed dressing up for teaching, and wanted to ensure my new wardrobe offered me the opportunity to dress well without over-purchasing.

Case in point: I no longer need a different ‘nice’ outfit every day of the week. Instead, this has been a money-saving discovery as I need fewer repeat items (since I don’t have to wear something for teaching every day – skirts, pants, etc.), waiting to launder them should I need them in between wearings. This excited me, but also put the responsibility into my hands to figure out what I would wear and then, what would I purchase that I would wear for a handful of years to come that would still look great (quality) and be timeless in its design. 

All of this took time. Another reason it took time had to do with my priorities during the past 4+ years. My focus aside from strengthening TSLL was also to finish the major renovation projects on my house. So most, if not all, of my discretionary money went to Le Papillon. 

With a sense of feeling more grounded in my daily routine, I am more confident in making investments in my wardrobe that I know will support the life of my responsibilities as well as how I love living and showing up wherever the day might take me. 

Perhaps some of this or all of it speaks to your journey of figuring out your wardrobe as well. Maybe you have had a life change in some way – a new job, a new town and thus way of moving through your day, becoming a parent, becoming an empty-nester, or maybe, your finances have shifted and you can finally invest in your wardrobe, or see the value of investing in your wardrobe and want to do so within your budget, therefore taking it slowly, but knowing your purchases will last. Whichever or whatever reason you are looking to strengthen your existing wardrobe, I welcome you along this 12-month journey. It will be your own, and hopefully, this series will provide you with ideas, tips, and tools to make decisions and purchases that leave you feeling both confident and at ease while also looking and feeling great. 

Where to Begin

1. Set a monthly amount you can dedicate to wardrobe purchases. Whatever that amount is, you will be purchasing one investment item each month. If that item is less than your allotted amount, you will carry over the difference. If it is over, you will subtract that from your next monthly allotted amount. So, we have wiggle room, but clarifying your budget ahead of time will help us decide what you will purchase and in what order. 
   
2. Create a list of 12-16 items you need.
   • NEED: Reflect back over the past two years, each season, annual events you attend, activities you enjoy, responsibilities you have – what clothing/accessories/shoes did you wish you had in your closet that were not there?
   • The reason I want you to reflect on the past two years is that there should be a pattern. This isn’t a list for one-off items such as items for a wedding or a reunion, etc. These should be items you want in your closet year after year, not special-occasion items. Those would fit into an entirely different part of your life and budget. 
     
3. After making your list of items (this includes shoes, accessories, jewelry, coats, handbags), if you already have a brand and a particular item you want, write that down next to it. 
   
4. This next step will take some time, but it will save you time (and money) later on:
   • Go find each item online and save it to KarmaNow. Write down the current price and place that price next to your item. 
     • If there are multiple places where your item is found, save it as well to KarmaNow.
   • By saving each item to KarmaNow, you will be alerted to any sales that occur to your item (not that you will purchase it if it isn’t on your schedule, but you will be able to potentially adjust your order of monthly purchases). You also have a secondary place cataloging your items for reference. 
     
5. Now, take out a sketch pad or a blank piece of paper, and I want you to visually draw each item on a ‘model’ so you can see how many items you plan to purchase for each part of your wardrobe.
   • The reason for this is not to be artistic, but to remind ourselves of whether we are purchasing a good balance of items. Too many shoes? Choose the two you absolutely need, then shift your attention to purchasing another pair of nice trousers or a brilliant, iconic handbag. 
     
6. Next, put the items in order (this can be rearranged later). For now, which items are likely to sell out more quickly due to seasonality or brand collections? For example, a iconic handbag like a Mulberry’s Bayswater or a Saint Laurent shoulder handbag will always be available – put such items at the bottom of your list. Put them in order from 1 to 12.
   • Write this on a list that you have with you regularly (I have mine in my planner – handwritten, so I can constantly edit with or without technology). 
   • Below you will see my list (I have blocked out my list as it will be shared with you gradually over the 12-month series
     • Once you have priced out the items, you will know what you can afford each month. But it is important you let the items guide you, not the price. For my first month (which will actually be talked about in February), only one item fit my budget. For the month of November, these two shoes, based on their sales price, fit my budget to buy both. 

Part One: Shoes for Everyday Life

Look beyond just one season – think year-round (not that you will wear the shoe year-round, but what do you need and currently lack). Assess which type of shoes you want to wear that would be both comfortable for the occasions you find yourself throughout the year regularly, but also look great to your eye?

In my own life, four types immediately come to mind:

• Loafers and pointed-toe flats
• Nude 85m leather pumps (matte)
• A high-top flat Chelsea boot that is water-resistant (for walking during October through April on trails in Bend)
• Dress boots (we’ll talk about this in further along in the series)
• Sneakers (not for running, but for walking while doing errands)
  • My Adidas retro sneakers spotlighted here are worn constantly during spring and summer (and while traveling and walking about the cities of Paris and London)
• Other shoes – sandals and trainers are already purchased and in my closet

What I was still missing when I began this 12-month approach were a Chelsea Boot and nude pumps. 

With my budget in mind, and knowing the retail price of the pumps I wanted, I was determined to wait until they went on sale. Sarah Flint’s nude leather pumps are wonderfully comfortable (a lot of padding in the sole), and well-made. I knew they were worth the full price, but since I wasn’t in a rush, I waited until the Black Friday Sale when they offered 35% off. 35% off! I swooped in and purchased a pair that were normally $495 for $325. 

Moving on to a boot I needed for my daily walks with Nelle: Since I typically will go walking with her each morning, and then follow it with tending to errands in town, I wanted a nice boot that looked great, but also provided the support and traction for autumn and winter walking. (I have snow boots for severe snow weather, but if it’s just cold or the path is easy to walk with packed snow, I wear these Chelsea Boots). 

I shopped around quite a bit for this boot as there are many brands of Chelsea Boots for utility purposes. Blundstones are one of the most popular, and so I ordered a pair of those at the beginning of my search, but I quickly discovered that with my high arch, their leather is not malleable enough and thus, they weren’t comfortable (loved the look of them though and they are well-made). Returning those, I found Barbour’s Evie Chelsea Boot, and while not waterproof, they are water-resistant which is all I needed as I have my wellies and my snow boots for extreme wet weather conditions. I paid full price as they didn’t have any discounts wherever I searched, but I did search. The moment I tried these on, I was in love. Comfortable, not too heavy, I love the design (high top, rather than the traditional style), and two finger grips to help easily pull the boot on. 

Takeaways from my purchasing experience:

1. First, choose the item you want, regardless of the price (within reason). Place it on your KarmaNow list. `
2. Then search around for promo codes, sign up for newsletters, and be willing to wait for a sale if you know one will eventually come up (Black November, end-of-season or year-end sales, etc.)
3. If in your budget, pay full-price (after having searched for ways to save). So long as you know it’s the item you need and want, that price, when viewed in hindsight, will be far less with the cost-per-wear concept applied. 
4. Be ready to return anything that doesn’t fit properly or cannot be taken to the tailor to customize to your silhouette. Having patience until you find what works best for you will pay off when you finally find the item that you love and that is comfortable. 

Let’s Shop Nude Pumps and Chelsea Boots for walking

Shop Barbour’s Evie boot at the below locations:

• Barbour
• Sole Trader

Similar Chelsea Boots:

• Blundstone’s Original high Top Boot (many colors)
  • Shop all of Blundstone’s Women pull-on boots here.

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Shop Sarah Flints’ Perfect Pump (85mm)

Sarah Flint’s Perfect Pump, 85 mm, nude

• Other heights and colors

Similar nude pumps, high quality (recommended)

• Stuart Weitzman
• Jimmy Choo
• Manolo Blahnik

Similar style, mid-luxury price

• Inez
• Quince
• Coach
• L.K. Bennett

The series continues!

This series, How to Build a Wardrobe to Love and Live In Every Day, continues with Part Deux next month on Tuesday February 10^th. 

Between now and then, work on creating your 12-16 item clothing/item list and following the six steps to curate this helpful guide that will keep you focused as well as bring peace of mind that you are investing in what you need and will love. 

SIMILAR POSTS YOU MIGHT ENJOY

~Explore all of TSLL’s Signature Style posts here