Sometimes a project idea that jumps into my head is straightforward: I set a goal and dive in. Bing. Bang. Boom. In a short time there’s a terrible before photo and a much-improved after.
Other times a project pulls me into a longer, unexpected process. My recent closet makeover did exactly that—evolving into something far bigger than a cosmetic fix.
I posted the images that launched the idea and imagined a few days of work would do the trick. Silly me. This project expanded into a thoughtful process that touched more than just shelves and hangers.
I found myself thinking about those organizing shows I used to watch—like Clean Sweep with Peter Walsh—where the team would help people who were overwhelmed by clutter. The transformation was practical, but it was also emotional. The hosts helped homeowners confront why they held onto things and walked them toward fresh starts in spaces that functioned and felt beautiful.
“I make a promise – you cannot make your best choice or your healthiest choice in a cluttered, messy, disorganised home; it just doesn’t happen. Your home should be a place you create that enables you to live the life you want.” ~ Peter Walsh
Now I’ll share a personal secret—lean in for honesty: I hadn’t been feeling my best. That admission was hard, but true. For years a few extra pounds and the habit of putting myself last kept me from investing time, energy, or even simple joy into how I looked now. I had convinced myself that I couldn’t bother with style or self-care until I was thinner. That mentality felt defeatist and limiting.
The closet project opened a door to deeper change. As I worked on organizing and beautifying the space, I also began to rethink how I dressed and how I wanted to feel every day. Around that time I discovered an online fashion course aimed at women over 40. For a modest fee it offered structure, guidance, and a fresh approach to the wardrobe I already owned.
That $24.99 investment turned out to be one of the smartest I’ve made. The course gave a shopping list and practical guidance to build a capsule wardrobe. I’d read that most people wear only 20% of their clothes 90% of the time—I want the 20% that actually works. The shopping list helped me focus on versatile pieces, and surprisingly, many of the suggested items were already in my closet. Each day the course sent a proposed outfit—21 combinations based on those core pieces—which made getting dressed simple and fun.
I found new confidence and joy through this process. I also joined a private Facebook group with other participants; it has been warm, encouraging, and motivating.
Now a new session is launching: the Winter Style Me Pretty Challenge. Here’s how it works, in summary:
How Does the Style Me Pretty Challenge Work?
You receive a curated shopping list of winter wardrobe essentials suitable for casual days and a few dressier looks for holiday events. The point is affordability and versatility—many pieces may already be in your closet, and you can shop where you like.
Once your capsule pieces are gathered, the program delivers 21 days of winter outfit combinations to your inbox. Each outfit can be worn the following day or saved for later. Outfits are downloadable and printable for easy reference.
What’s Included:
- Winter/Holiday Basics Shopping List – Essential winter items with recommended examples and a downloadable PDF to take shopping.
- 21 Days of Daily Outfits – A unique outfit each day created from the shopping list pieces. Outfits are released at 7:00 p.m. ET the night before so you can prepare. New this season: dressy outfits are released with the shopping list.
- Private Facebook Group – A members-only group to share looks, ask questions, and encourage one another. Many participants say this is the most enjoyable part of the experience.
What Kind of Outfits?
The challenge focuses on cozy, casual looks for busy days plus several dressier options for holiday gatherings. You can adapt any suggestion to your comfort level and personal style.
Cost and Investment
One-on-one styling services can be costly, but this group challenge is designed to be affordable and accessible. Participation is offered at a modest fee, and you control how much you spend on new pieces. Many recommended items are from approachable retailers, and each piece is styled multiple ways to maximize your wardrobe.
Winter/Holiday Challenge Timeline:
- November 21 – Registration opens.
- November 27 – Regular registration closes at midnight ET; late registration opens.
- November 28 – Black Friday – Shopping list and dressy looks are released at 12:01 a.m. ET.
- December 7–27 – Daily outfits are delivered at 7:00 p.m. ET each evening.
Registration opens Friday, so you’ll have a moment to consider whether you’d like to join. If you decide to try it, there’s a small affiliate link on my site that helps support me when you sign up.
That tiny support might just help me buy the cute boots I’ve been eyeing. And because I promised honesty, here’s a selfie of one of my outfit-of-the-day looks—proof that small changes can spark bigger ones.
I’ll update you this week with progress on the closet project—fair warning, it’s still a work in progress. I’d love for you to join me on this journey to a more organized closet, a more confident wardrobe, and a prettier everyday life.
