Welcome to the 28-Day Style Challenge: Refine Your Wardrobe! This challenge is designed to help you rediscover the magic in your wardrobe, help you refine your style and normalise wearing what you love. I do this at the start of February each year, but you can start anytime.
By the end of the 28 days, you will have clarity on what you like and what you’ve outgrown. You will have a set of prompts to give you plenty of inspiration for rethinking and reworking your existing pieces; you’ll uncover new ways to express yourself and build outfits.
I run this challenge every February — and last year, it changed everything.
For 28 days, I captured my outfits.
I experimented. I played.
And by the end? I was shocked. My style had evolved. My body shape had shifted. But my wardrobe hadn’t kept pace.
The style Challenge That Transformed My wardrobe
This challenge didn’t just help me rediscover pieces I’d forgotten – it gave me the clarity to realise there were ones that no longer belonged – keeping me stuck.
It became a turning point: a moment of honest reflection on who I was becoming and whether my wardrobe reflected that identity. That’s the power of this challenge. It’s not about buying more. It’s about seeing more — in what you already own, and in yourself. The art of refinement…
The Moment Everything Shifted
It was last year within the first week of the challenge – I’d pulled out a coat I’d owned for years — one I’d worn proudly on repeat. It had been a staple.
But when I put it on and looked back at the photos, something felt wrong. It wasn’t me anymore.
The coat just fit differently. It wasn’t the coats fault, it was me. I’d changed – I was so set on being sustainable, and not buying new things – I had started to make do. And this was an outfit for the woman I was 10-years ago. The coat that once made me feel vibrant now felt like a costume from a previous chapter.
That’s when I understood what this challenge was really about.
The 28-Day Style Challenge not just a sustainable styling exercise. It’s a creative mirror. One that shows you — with uncomfortable clarity — where your wardrobe is aligned with who you are, and where it’s still holding onto who you used to be.
By the end of the 28 days, I had released more than a dozen pieces. Not because they were worn out — but because I had outgrown them.
And in their place? Space. Clarity. Permission to dress as the woman I’m becoming.
Permission to start investing in my wardrobe again, after a decade of holding back… Permission to embrace what makes me feel truly confident.
What Is the 28-Day Style Challenge?
The 28-Day Style Challenge is a curated set of daily styling prompts designed to help you:
- Reconnect with pieces you’ve overlooked
- Experiment with new combinations you’d never have tried
- Discover what makes you feel most like yourself
- Release what no longer aligns with your evolving identity
Each day, you’ll simply follow a creative prompt.
Style an outfit.
Capture it.
Reflect.
By the end of the 28-days? You’ll have a visual diary of your styling — and a clearer sense of what belongs in your wardrobe going forward. I share my daily looks on Instagram Stories throughout the challenge. Feel free to join me.
Who Is This Challenge For?
This challenge is designed for women who are ready for more from life, and less wardrobe stress. This 28-Day Style Challenge is more than just being creative. Its about taking time to review who you are and what’s hanging in your wardrobe.
It’s for women who are ready to:
- Dress with more style intention — without defaulting to shopping for new trend pieces
- Feel disconnected from their wardrobe after a life or career transition
- Invest time in themself and align their wardrobe with their refined identity
- Wear clothes that elevate – and translate who they are and how they want to feel.
Whether you’re navigating a new chapter in life, stepping into a leadership role, returning to the office, or simply ready to feel more aligned in what you wear — this challenge meets you where you are.
Why Take the STYLE Challenge?
Style clarity and dressing in line with our identity is an overlooked part of our personal development. But it shouldn’t be. Trends come and go, but your sense of who you should remain. When we evolve – our wardrobes, and our sense of style should too. This challenge is a chance to reset, refine and review your style.
1. Shop Your Wardrobe First
Before investing in anything new, discover what’s already there. Most wardrobes are full of untapped potential — pieces bought with intention but never fully explored. This challenge helps you uncover them.
2. Build Creative Confidence
Styling prompts push you beyond your default combinations. You’ll discover fresh ways to wear familiar pieces — and build the kind of creative confidence that extends far beyond your wardrobe.
3. Normalise Rewearing With Pride
There’s power in wearing what you love — again and again. Women with great style aren’t afraid to repeat their outfits. This challenge celebrates outfit repeating, intentional dressing, and the joy of a wardrobe that truly works for you.
4. Clarify Your Style Identity
By the end of 28 days, you’ll have visual evidence of what makes you feel most like yourself. Playful? Polished? Bold? Minimal? Your style identity will emerge — and you’ll have the images to prove it.
1. Shop Your Wardrobe First
Before investing in anything new, discover what’s already there. Most wardrobes are full of untapped potential — pieces bought with intention but never fully explored. This challenge helps you uncover them.
2. Build Creative Confidence
Styling prompts push you beyond your default combinations. You’ll discover fresh ways to wear familiar pieces — and build the kind of creative confidence that extends far beyond your wardrobe.
3. Normalise Rewearing With Pride
There’s power in wearing what you love — again and again. This challenge celebrates outfit repeating, intentional dressing, and the joy of a wardrobe that truly works for you.
4. Clarify Your Style Identity
By the end of 28 days, you’ll have visual evidence of what makes you feel most like yourself. Playful? Polished? Bold? Minimal? Your style identity will emerge — and you’ll have the images to prove it.
Your 28 Daily Styling Prompts
Each prompt is designed to stretch your creativity while working entirely with what you own. This experience is designed to help you see you wardrobe and how you style your clothes in a new light. It’s an opportunity to reset, realign and redesign life and your style on your terms.
No trends. No Pantone colour of the year. No rules.
Day 1: Love Layers
Experiment with layering — tops under dresses, jewellery stacked, textures combined.
Try: A button-down shirt under a sleeveless dress, or a chunky cardigan over a fitted turtleneck.
Day 2: Colour Block
Wear three or more colours in one outfit. Use the colour wheel for inspiration.
Try: Cobalt trousers, mustard top, and a pop of fuchsia in your accessories.
Day 3: Colour Coordinate
Pair complementary colours — opposites on the colour wheel — for an intentional, elevated look.
Try: Orange blouse with a navy skirt. Forest green dress with a burgundy belt.
Day 4: Backwards
Wear a top or jumper back-to-front for a fresh silhouette.
Try: A deep-back knit worn as a V-neck. A structured shirt reversed for a new neckline.
Day 5: Mono Texture
Create a monochrome outfit using varied textures.
Try: Velvet blazer, satin trousers, cotton tee — all in the same shade.
Day 6: Address It
Style a dress as a top or skirt through layering.
Try: A slip dress under a cropped jumper becomes a midi skirt.
Day 7: Repeat
Rewear a favourite outfit — but switch one element to refresh it.
Try: Swap heels for trainers. Add a scarf. Change your jewellery.
Day 8: Clash It
Combine two patterns for an unexpectedly harmonious look.
Try: Stripes with florals. Leopard with checks. Let colour be your unifier.
Day 9: Colour Pop
Add one bold accent to an otherwise neutral outfit.
Try: Black jumpsuit with a red bag. Grey suit with neon earrings.
Day 10: Forgotten
Style a piece you haven’t worn in months. Does it still feel like you?
Try: That statement jacket you bought with excitement — pair it with your favourite basics and see.
Day 11: Neutrals
Build an outfit entirely from sophisticated neutral tones.
Try: Cream, camel, and taupe layered together. Let texture create the interest.
Day 12: Restyle
Take yesterday’s outfit and wear the same pieces differently.
Try: Knot the shirt. Add a belt. Roll the sleeves. Transform without changing a thing.
Day 13: Relay
Carry forward one piece from yesterday and build a new outfit around it.
Try: Keep the blazer. Change everything else.
Day 14: Wow Colours
Wear your boldest red or pink. Happy Valentine’s Day — dress for yourself.
Try: Red midi dress with pink accessories. Or pink blouse with red trousers.
Day 15: Accessorise
Build an outfit starting with a standout accessory.
Try: Choose the bag, the earrings, or the shoes first — then dress around them.
Day 16: Upside Down
Wear something unconventionally — literally or figuratively.
Try: A cardigan buttoned at the back. A scarf as a belt. Challenge convention.
Day 17: Repeat
Rewear your favourite outfit from the challenge so far. Wear it with pride.
Day 18: Oops
Style something imperfect — a tear, a stain, a loose button.
Try: Layer creatively. Turn the flaw into a feature. Or decide it’s time to let go.
Day 19: Dress It Down
Make an evening piece work for day.
Try: Sequined skirt with a cashmere knit and trainers.
Day 20: Base Colours
Build from black, grey, or white — and let subtle accents do the work.
Try: Tonal dressing with one elevated detail.
Day 21: Iron It
Wear that piece you’ve been avoiding because it needs pressing.
Try: The linen trousers. The crisp white shirt. Give them their moment.
Day 22: Elevate It
Take a simple piece and dress it up for evening.
Try: Basic black dress with bold earrings, a belt, and heels.
Day 23: Easy Going
Style loungewear or athleisure for an elevated, polished look.
Try: Joggers with a blazer and gold jewellery.
Day 24: Repeat
Rewear your favourite look from this week.
Try: Add a hat, swap the shoes, or style it exactly the same.
Day 25: Love Layers (Revisited)
Return to layering with fresh combinations.
Try: Sleeveless top over a long-sleeved turtleneck. A dress over trousers.
Day 26: Relay (Revisited)
Carry one piece forward from yesterday’s outfit.
Try: Same jeans, completely new outfit around them.
Day 27: Pattern Clash
Combine at least two prints intentionally.
Try: Leopard with plaid. Stripes with spots. Let colour harmony unite them.
Day 28: Repeat — The Finale
End on a high. Wear the outfit that made you feel most like yourself.
This is your signature look. Capture it. Celebrate it. Wear it again and again.
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CAPTURE YOUR LOOKS
This challenge is all about having fun, building confidence, and embracing creativity with what you already own. By the end of the 29-Day Style Challenge, you’ll have a deeper appreciation for your style, what you like, what you love in your wardrobe (and what you don’t), new styling ideas, and a set of new and unexpected ways to express your personality through your existing outfits.
Last year I captured my looks and I was shocked to realise my sense of style (and body shape) had shifted to much, yet my wardrobe had caught up. For me, this challenge helps me refine my style and release items that no longer work for me.
What Happens After the 28 Days?
By the end of this challenge, you’ll have:
- A visual library of outfits that work (and very importantly ones that don’t)
- Clarity on your evolving style identity
- Permission to release what no longer belongs, what no longer fits, what no longer brings you joy
- Confidence in your ability to dress with intention
For some, this is the beginning of a deeper transformation. If you want support refining your wardrobe, aligning your style with your identity, and building a capsule wardrobe that truly works for you and your lifestyle – book a Private Style Consultation to explore working together.
Frequently Asked Questions
When does the challenge start?
I run this challenge in February each year — but you can start any time. The prompts work whenever you’re ready.
Do I need to buy anything new?
No. This challenge is designed entirely around what you already own. That’s the point.
What if I work from home or have a casual dress code?
Perfect. Adapt the prompts to your life. The goal is to reconnect with your wardrobe — however you dress day-to-day.
Can I do this privately?
Absolutely. You don’t need to post anything publicly. Capture your looks for yourself — that’s where the real insight lives.
What if I realise my wardrobe isn’t working?
That’s powerful clarity. It’s exactly what happened to me. If you want support building a wardrobe that reflects your identity,
I’m here to help.
Join me for the next 28 days.
Reconnect with your wardrobe.
Discover what makes you feel most like yourself.
And build the confidence to dress with intention — every single day.
Style isn’t about clothes. It’s about who you become in them.
Roberta
