HER Style Podcast | Episode 307
The ‘Almost Right’ Outfit Problem: When Every Look You Try Feels 80% There
Host: Heather Riggs | January 15, 2026

Episode Overview

In this episode, Heather Riggs tackles the all-too-familiar “almost right” outfit problem—when your ensemble seems perfect in your head but falls short in the mirror. Heather explores why this happens, why copying influencers rarely works, and why this frustrating near-miss is actually a sign of progress on your style journey. The episode is both practical and encouraging, offering listeners actionable insights for turning good outfit ideas into great personal style.

Key Discussion Points & Insights

1. The “Almost Right” Outfit Problem Defined

Timestamp – 00:00

• Heather sets the scene: envisioning a fabulous outfit, only to be underwhelmed when everything is on.
• The cycle: adding, subtracting, and swapping items—yet never getting it quite “there.”
• Quote:
  “It might not be the worst outfit you’ve ever worn or even bad, but it's just not what you imagined. And you can't quite put your finger on why.” (A, 00:16)

2. The Universality of the Problem—even for Stylists

Timestamp – 01:44

• Heather normalizes this frustration, admitting it still happens to her after years as a professional.
• Personal anecdote: Her “Christmas outfit fail”—the vision of a colorful, elegant holiday outfit undermined by untested color combinations.
• Quote:
  “Even after years of styling, I will sometimes have a crystal clear vision of what I want to wear. I pull the pieces, I put it on, and it's not what I thought it would be.” (A, 01:44)
• Memorable story of getting ready for her son’s choir performance and realizing last minute the colors clashed, leading to disappointment and frustration.

3. The Two Most Common Reactions

Timestamp – 06:40

Heather identifies two default responses women have when outfits don’t come together:

1. Retreating to Familiar “Safe” Clothes
   • “You keep defaulting back to what you've done before because it feels low risk. And eventually you just stop experimenting.” (A, 07:19)
   • This can cause style stagnation and sap the fun from getting dressed.
2. Buying More Clothes
   • “You decide it’s just time to go buy more things… Instead of knowing how to bring an outfit together, you're just grasping at straws.” (A, 08:12)
   • The cycle of shopping for newness as a quick fix rather than learning how to style what’s already owned.

4. The Limits of Copying and Outfit Inspiration

Timestamp – 09:10

• Heather warns against relying solely on inspiration from influencers, Pinterest, or mood boards:
  • “Inspiration shows you the picture… but it doesn’t give you the process.” (A, 09:57)
  • Influencers are incentivized to sell specific items, often skipping the why and how of styling.
• Final outfit tweaks—the “last 20%”—are highly individual:
  • “What looks effortless on someone else depends on their body, their proportions, their coloring, their lifestyle, their energy and comfort level.” (A, 10:40)
  • Copying a look doesn’t teach you to craft new, unique outfits for yourself.

5. The Surprising Good News

Timestamp – 11:38

• Feeling “almost right” signals strong style instincts and taste, not failure.
• Biggest missing puzzle piece is a personalized approach to styling—adapting looks to who you are and what you own.
• Quote:
  • “If your outfits feel almost right, not totally right, that's actually really good news. Seriously. Because it means that your taste is already there... you're not starting from ground zero.” (A, 11:38)

6. The Importance of Process over Inspiration

Timestamp – 12:13

• The solution is not another shopping spree or more pinning, but learning the skills to style what you have.
• Heather introduces her upcoming “Shop Your Closet Challenge,” designed to help listeners bridge the gap between vision and reality—without new purchases.
• Summary of the challenge:
  • “Inside this challenge, I'm showing you how to work with what you already have so that the outfits in your head actually look amazing on you when you wear them in real life.” (A, 12:24)
  • Focus is on process, mindset, and building confidence in personal styling.

Notable Quotes & Memorable Moments

• “This still happens to me. Even after years of styling… if I don't plan ahead, I am sometimes forced to leave the house in a look that is not my favorite.” (A, 01:44)
• “You just don't want to feel disappointed again when you try to do something different and it doesn't work out.” (A, 07:32)
• "Copying an outfit doesn't teach you how to finish the next one… You know what you like in your head, but you don't know how to make it work for you in your real life consistently." (A, 10:57)
• “If your outfits feel almost right… that's actually really good news.” (A, 11:38)

Important Timestamps

• [00:00] Introduction to the “almost right” outfit feeling
• [01:44] Heather’s personal story of a holiday outfit gone wrong
• [06:40] Why we default to familiar outfits or shop for more
• [09:10] The myth of outfit inspiration and copying influencers
• [10:40] The personal nature of the finishing touches
• [11:38] Why “almost right” is positive—your taste is there
• [12:13] The “Shop Your Closet Challenge” announcement

Final Takeaways

• Many women have good taste and vision but lack a personal styling process—this is normal and fixable.
• Copied outfits rarely yield consistent satisfaction; personalization is key.
• Feeling dissatisfied means you’re ready for the next level.
• Heather provides actionable support through her “Shop Your Closet Challenge,” focusing on using what you already own and building confident styling skills.

For Further Support

• Shop Your Closet Challenge: January 27–29, 2026 (info at herstylellc.com/challenge)
• Signature Style Reset Masterclass: Complimentary with challenge registration.
• Free Personal Style Quiz: Link in show notes and at herstylellc.com/quiz.

Heather’s tone is warm, empathetic, and practical—encouraging listeners not to be discouraged by “almost right” outfits, but to see them as signs of progress in developing a signature style.