Podcast Summary: HER Style Podcast

Episode 269 | When to Get Rid of Something and When to Try Harder to Style It [LIVE Coaching!]
Host: Heather Riggs
Date: September 1, 2025
Guest: Meg (Live Coaching Session Winner)

Episode Overview

This episode features a live coaching session with Meg, a member of Heather's community and the recent winner of a Wardrobe Revamp Bootcamp prize. Together, they tackle some of the most common wardrobe struggles:

• When to let go of clothes versus when to try styling them differently
• How transitioning to gray hair might affect your color palette
• Strategies for wearing deeper, darker colors without being overwhelmed
• Tips for choosing or refining personal “style words” to guide your wardrobe

Heather delivers practical, compassionate advice for anyone who feels stuck with a closet full of clothes that just don't feel right.

Key Discussion Points & Insights

1. The Emotional Challenge of Wardrobe Evolution

Meg describes her style journey since turning 50 and feeling disconnected from clothes she previously bought.

• Meg shares that after her 50th birthday, she began to focus more consciously on her style, realizing many items no longer “light her up” or suit her updated knowledge of her body shape and best colors.
• Heather reassures listeners this is “completely normal,” emphasizing that wardrobes naturally evolve with us.

“It might feel a little frustrating when you look at your clothing, and it’s not completely matching up the way that you want, but it’s good to recognize that, and now you can feel empowered to start making some shifts.” – Heather (03:46)

2. Avoiding Perfectionism and “All-or-Nothing” Thinking

• Heather addresses Meg’s concern about overanalyzing, perfectionism, and the “good enough” dilemma.
• She recommends allowing for a gradual transition rather than purging everything at once.

“It’s progress over perfection... give yourself permission to fall in love with the process and to enjoy taking it one little baby step at a time.” – Heather (05:16)

Practical Tool: Closet Audit Flowchart

• Heather suggests using her free Closet Audit Flowchart to make objective decisions and break the cycle of emotional or perfectionist thinking.
• The flowchart offers additional options beyond “keep or toss” (like “replace”, “repair/alter”, or “remove”).

“You don’t need to remove [frustrating pieces] from your wardrobe, but you might want to gradually replace over time… not like keep or let go – it's keep, replace, maybe repair or alter, or remove.” – Heather (07:55)

3. When to Keep, Restyle, or Remove Items

• Set a timeframe to try restyling a piece (e.g., one week or one month). If it still isn’t working after the trial, let it go.
• Keep “replacement” pieces in a separate closet section to track how often you actually reach for them.

“You never want to work too hard to feel good in your clothing. So if you’re trying to make something work and it’s just not working... I think you can feel okay about letting it go and moving on to better things.” – Heather (10:00)

“It’s always better to have less items that you really love than a lot of things you’re not excited to wear.” – Heather (10:25)

Listener Fear: “I’ll regret tossing something I might need later.”

• Meg admits she fears missing pieces she lets go.
• Heather recommends the “replace” approach: keep less-than-ideal pieces temporarily while noting which ones you’d rather update.

“Put those pieces in a whole separate section of your closet so you can notice how often you’re reaching for them.” – Heather (11:30)

4. Balancing Wardrobe Size, New Buys, and Guilt

• Meg feels guilt over buying new while still having too much.
• Heather suggests freeing up space by letting go of the “just okay” items to make room for new pieces you’ll actually wear and love.

“Get rid of all the things that you’re kind of dreading wearing in that challenge... You don’t have to force yourself into those things.” – Heather (13:59)

Style & Color Questions

5. Transitioning to Gray Hair—Do Your Best Colors Change?

• Meg is embracing her silver hair and wonders how it affects her color palette.
• Heather explains three main changes:
  • Hair going gray usually calls for slightly cooler colors.
  • Gray can “soften” your palette, making muted tones more flattering than intense, bright ones.
  • Your personal color contrast likely lowers (less distinction between skin, eyes, hair).
• Heather suggests trying softer, cooler shades and using a bolder lip or blush if you want to offset muted clothing.

“You might look better in more muted tones or pastels… and your overall contrast level a little bit lower as well.” – Heather (16:00)

6. Wearing Deep, Dark Colors Without Overwhelm

• Meg loves burgundies and chocolates but worries they’re now too harsh.
• Heather clarifies that “contrast” is about the difference between lights and darks in YOUR OUTFIT, not just your skin/hair vs. the garment.

“Contrast is different than the depth of color… If you have low contrast, your outfit is probably going to look best if it also doesn’t have a stark difference between lightness and darkness.” – Heather (17:19)

Practical Tip:

• You can wear deep, dark colors—just combine them with similar-depth colors for a monochromatic look, avoiding extreme contrast with your skin or within your outfit.

“If you want to wear chocolate browns and burgundies… a subtle monochromatic would be nice… it won’t overpower you.” – Heather (19:30)

Signature Style Words—How to Find and Use Them

7. Defining Your Personal Style with “Style Words”

• Meg is pondering her “style words” but struggles with broad categories like “classic.”
• Heather’s process:
  • Build a style mood board (Pinterest, for example) to see visuals you resonate with.
  • Pull your top 10 favorite wardrobe pieces and note their qualities (“style values”).
  • Reverse engineer: choose style words that reflect the themes/patterns you discover.

“There’s variation to every style type…try to pinpoint your style values. It could be versatility, comfort… maybe something about the fit.” – Heather (21:00)
“Reverse engineer the words—maybe don’t start with that if you’re getting stuck.” – Heather (22:28)

Notable Quotes & Moments

• “For most of us, we don’t have the luxury to just throw everything away and buy a whole new wardrobe overnight… be okay with starting slow.” – Heather (05:28)
• “I love that challenge—what a fun idea to do for yourself… I bet you’ve come up with lots of new outfits.” – Heather, on Meg’s “wear everything in the closet” challenge (12:17)
• “If you can afford to pare down a bit and maybe simplify…I’d rather you have four tops you absolutely love, than 14 that you don’t.” – Heather (10:25)
• “I always want people to notice you… your outfit is like, a secondary complement to that.” – Heather (18:42)

Timestamps for Key Segments

• [02:49] Meg’s style journey and current wardrobe dilemma
• [05:16] Progress over perfection – starting slow with wardrobe changes
• [06:51] How to use the Closet Audit Flowchart
• [09:54] When to challenge yourself to restyle vs. when to let go
• [11:30] “Replace” category and tracking real use
• [13:29] Balancing new buys with guilt over existing wardrobe
• [15:21] Transitioning to gray hair and the impact on color palette
• [17:19] Understanding contrast vs. depth in outfit colors
• [21:00] How to discover your authentic style words

Takeaways & Advice

• Wardrobe change is a process, not an overnight fix; be patient and strategic.
• Let love and likelihood-of-use be your filters when deciding what to keep or let go.
• Use a flowchart or objective system to reduce emotional decision-making.
• Embracing grays may invite softer, cooler, and lower-contrast color combinations—but doesn’t mean abandoning cherished deeper colors.
• Finding your “style words” may be easier by looking at what you’re naturally drawn to, not starting from catch-all fashion terms.

Resources Mentioned

• Closet Audit Flowchart: herstylellc.com/closet-audit
• Style Mood Boards and Quizzes: herstylellc.com/quiz
• Wardrobe Revamp Bootcamp and Community: herstylellc.com/bootcamp

This power-packed coaching session delivers practical, empathetic guidance for anyone navigating the confusing “should it stay or should it go?” phase of their style journey. Heather’s patient, systems-based approach makes the daunting process of revamping your wardrobe both accessible and a little more joyful.