A Winter Capsule Wardrobe Overhaul in 10 Steps

It became less about self expression and more about status.

We became so focused on staying fashionable, relevant, and on trend that we lost the parts of fashion that resonate with us as individuals.

I’m currently having an internal battle with fashion, style, consumerism, and downsizing. This is making me reflect on my personal style and note if there are any shifts in different directions.

What is Individualism in Fashion?

Individualism in fashion is the use of clothing, accessories, and style choices to authentically express your unique personality, values, and preferences.

The emphasis is on self-expression and creativity over adherence to trends or societal expectations.

With a focus on individualism, fashion becomes a tool for telling your story, showcasing your identity, and celebrating your differences, instead of keeping up with the Jones’ or trend chasing.

The new year is always a good time to think about this because it is the calm after the storm, and Christmas tends to make us want to clean, purge, and downsize.

So unless you are 100 percent certain, than it is okay to hold onto something to see if you come back to wear it again in the future. You can always revisit donating later, because it is not an action that you can take back.

• Sort: Create three piles: Keep, Donate/Sell, and Toss.
  • Keep: Items you love, wear often, and fit well.
  • Donate/Sell: Items but only if you are sure.
  • Toss: Worn-out or damaged items that can’t be repaired.

• Questions to Ask:
  • Does this fit me properly?
  • Have I worn this in the past year?
  • Does this align with my lifestyle and style goals?
  • Do you feel a genuine connection to this item, or is it just “good enough”?

Pro Tip: Be ruthless—if it doesn’t spark joy or serve a practical purpose, it’s time to let it go.

Step 2: Define Your Style

A wardrobe overhaul is the perfect opportunity to refine or even reinvent your personal style. Knowing what you’re aiming for will guide all your decisions moving forward.

• Inspiration: Create a mood board using Pinterest, Instagram, or magazines. Pin outfits and pieces that resonate with you.

• Identify Patterns: Look for common themes in your inspiration.

Do you gravitate toward classic silhouettes, bold prints, or a minimalist aesthetic? Over time, a pattern will emerge, giving you insight into your authentic style.

• Style Quiz: Ask yourself:
  • What makes me feel confident?
  • Which colours, fabrics, and silhouettes do I naturally gravitate toward?
  • How do I want to be perceived through my style?
  • Who are my style icons, and what about their looks resonates with me?

Once you’ve clarified your preferences, jot down a few key descriptors for your style or style adjectives which I talk about in detail in this post.

For example: words, word combinations like “effortlessly chic,” “modern and edgy,” or “classic and preppy.”

I have been putting together capsules with these words or hybrids of words for years in order to help give you some ideas of how you can wear things if you relate to a particular style or style adjective.

Step 3: Build a Capsule Foundation

Every great wardrobe starts with a foundation of key pieces that you can’t do without.

• To Me, Those Pieces Are:
  • Oversized sweaters
  • A pair of vintage jeans that you will live in.

My favourites vintage jeans are Levi’s with a preference for the 501 and 505 models. I am currently thinking about spring and I want to get a pair with a shorter inseam so they are ankle skimming.

This length will pair well with flats, sandals, and boots, but can also be cuffed to a shorter length for summer or wear a higher shaft boot under during the cooler season. I like to think how pieces will work in every single season, not just the current.

• A blazer or light coat in an interesting cut. I like asymmetrical or deconstructed.

Think pieces from Maison Margiela, Junya Watanabe, or Yohji Yamamoto. Almost like futuristic minimalist. They are designers I am currently seeking.

• Interesting shoes
• A versatile dress. Mine is a black slip dress.
• A statement bag or two. Always secondhand.

• Focus on Quality: These pieces should be durable and timeless, so prioritize quality over quantity.

When I say timeless I don’t mean like traditional classic style. I just mean something that isn’t focused on a certain trend, that is so interesting or unusual and can’t be placed to a specific time period.

This is one reason that I love shopping secondhand and vintage.

• Checklist: Create a checklist of wish list pieces based on your style goals.

• Research: Identify brands and stores that align with your style and quality standards.

• Try On: When possible always try items on before purchasing.

A perfect fit can make even a simple piece look incredible, but if it isn’t possible than it is important to know your measurements. Keep this written down somewhere.

Always go by measurements, not by size. Vintage fashion fits differently, and modern fashion has sizing that is often very inconsistent.

• Shop Smart:
  • Prioritize pieces that are perfectly you over fleeting trends.
  • Shop during sales or consider secondhand options for sustainable choices.
  • Stick to your list to avoid impulse buys.

Pro Tip: If you need to adjust the fit to make something work, find a good tailor. A few alterations can transform the fit of almost any garment.

Step 6: Organize Like a Pro

An organized closet not only looks great but also makes getting dressed a breeze. I have been working through this step myself this week.

• Declutter: Donate or sell items that no longer fit your vision.

• Invest in Storage:
  • Matching hangers for a uniform look
  • Storage bins for seasonal items
  • Drawer dividers for accessories and undergarments

• Display Thoughtfully: Arrange clothing by category (e.g., tops, bottoms, dresses) and then by colour for a boutique-like feel.

I don’t always do the colour organization but I definitely organize by category.

Pro Tip: They often say to keep frequently worn items easily accessible and store special occasion pieces separately. But I don’t think you should save your pieces for unknown special occasions.

Wear your clothes. All of them, for any reason not just special.

Step 7: Accessorize Thoughtfully

Accessories can elevate even the simplest outfits and add personality to your style.

• Statement Pieces: Invest in standout items like a designer handbag (secondhand), bold jewellery, or unique shoes.

• Everyday Essentials: Stock up on versatile accessories.

Pieces such as a leather belt, classic sunglasses, and dainty jewellery for quick and easy pairings.

• Seasonal Swaps: Rotate accessories like scarves, hats, and bags.

This will keep your outfits fresh and weather-appropriate.

Pro Tip: Use accessories to experiment with trends without committing to larger wardrobe changes.

Step 8: Evaluate Regularly

Your wardrobe is an evolving project that requires regular attention.

• Seasonal Check-Ins: Revisit your wardrobe every three to six months.

Declutter items you no longer wear and assess gaps for the upcoming season.

• Trends vs. You: Incorporate trends sparingly to keep your wardrobe fresh while maintaining your overall aesthetic.

• Adjust as Needed: As your lifestyle changes, adapt your wardrobe accordingly.

Personal style is not static. As you grow, your wardrobe should evolve with you. Regularly revisit your closet, reflect on what works, and adjust as needed.

Experimenting and taking risks can lead to unexpected discoveries.

Pro Tip: Keep a running wishlist to track items you’d like to add and prioritize them during your next shopping trip.

Step 9: Take Care of Your Clothes

Preserving your wardrobe ensures your pieces last longer and stay in great condition.

• Washing: Follow care labels to avoid shrinking or damaging fabrics.

• Storage: Use garment bags for delicate items and fold knitwear to prevent stretching.

• Repairs: Learn basic sewing skills or have a trusted tailor for mending seams, replacing buttons, or altering pieces.

Step 10: Embrace the Process

Overhauling your wardrobe isn’t an overnight task, but it’s incredibly rewarding. Take your time to enjoy the journey of rediscovering your style.

• Celebrate Small Wins: Even adding one perfect piece can be a big step.

• Document Your Progress: Take photos of your favourite outfits to track your evolving style.

• Stay Inspired: Continue exploring new looks and experimenting with different combinations.

Remember, your wardrobe is a reflection of you, not some preconceived ideal of what you should be.

I am now offering digital styling guides, and personal styling services. If you are looking for some styling help that is inexpensive and easy, check out my digital styling guides. If you want some one-on-one help shopping, building and editing your wardrobe, or packing for a trip, I can also assist. Check out all the styling services that I offer here.

This post contains affiliate links. By using my links to shop I may receive a small commission (at no cost to you). Thanks for supporting what I do 

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