Happy Saturday!
I’m spending the day at a local craft fair, but I wanted to pause and share an update about a fashion challenge I’ve taken part in and why I think it’s a great experience for anyone looking to refresh their wardrobe confidence.
Some time ago I joined a Style Me Pretty Challenge hosted by Alison from Get Your Pretty On. In short, the challenge is a guided styling program that helps you create multiple polished outfits from a limited selection of pieces. It’s designed to make dressing easier, more creative, and more fun—especially if you tend to wear the same looks or feel unsure about how to mix and match what you already own.
How the challenge works
- After you sign up, you receive a shopping list that outlines all the pieces used in the current challenge. You can follow the list and buy similar items, or you can skip shopping and use what you already have in your closet.
- When the challenge begins, you get an email with an “outfit of the day” and clear directions for assembling each look. The program guides you through several outfit combinations so you learn how to create many stylish ensembles from a few key garments.
This particular session is the Winter 2015 challenge, which includes not just 21 outfits but 26 total outfit ideas. Each outfit typically has both dress-up and dress-down options, making the looks versatile for different occasions and moods.
Why I recommend it
I’ve participated in more than one of these challenges, and they’ve been surprisingly helpful. Beyond giving practical shopping guidance, the program boosted my confidence with styling. Even as an over-40 mom, I want to look and feel stylish—and this challenge nudged me to try combinations I might not have considered on my own.
The experience encouraged me to start sharing my outfits in a regular Fashion Over 40 series on my blog, which was a fun way to document progress and get comfortable being more visible about personal style. There’s also an optional private Facebook group for participants that I found to be a warm and encouraging space. If you enjoy community support, that part of the challenge can be a real highlight.
Is this right for you?
If you like the idea of learning how to mix and match with intention, or you want a straightforward way to shop smarter, this type of styling challenge can be a helpful gift to yourself. It’s also a nice suggestion as a present idea—think of it as an early-season surprise or stocking stuffer for someone who enjoys fashion and transformation.
On my site you’ll find a banner image that will direct you to sign up if you decide to join. Early registration often comes with a reduced rate for those who enroll sooner rather than later, so if you’re interested it’s worth checking out the details while the offer is available.
Whether you join or simply take inspiration from the approach—examining your closet, trying new combinations, and giving yourself permission to play with style—you’ll likely come away with more outfit options and a little more confidence in how you present yourself.
Have a lovely day, Pretties!
**I am an affiliate member of the Style Challenge. If you sign up through a link I share on my site, I will receive a portion of the sale. Thank you!
