Podcast Summary: The Everyday Style School

Episode: Stop Making These 5 Fit Mistakes
Host: Jennifer Mackey Mary
Date: September 23, 2025

Episode Overview

In this episode, Jennifer Mackey Mary dives deep into the nuanced world of clothing fit—a “style fundamental” that trumps trends, color palettes, and body shape advice. With over two decades of dressing real women, she breaks down the five most common mistakes women make with fit, debunks common myths, and offers practical actionable advice so your wardrobe flatters and serves you—no matter your size, shape, or budget.

Key Discussion Points and Insights

1. Confusing “Fit” With “Fit”

[03:19-11:48]

• Problem: Many women conflate “fit” (the correct size for their body) with “fit” (the cut or style of a garment, e.g. bodycon, relaxed, oversized).
• Insight: Sizing up for a “relaxed” look often leads to clothes that don’t fit well overall—the sleeves get longer, the neckline gets baggier, and everything becomes sloppy.
• Advice:
  • Read item descriptions carefully. Look for how the garment is intentionally cut: relaxed, oversized, regular, or fitted.
  • Quote:

    “To get clothes that have the closeness to your body that you’re looking for, you have to adjust with cut, not size.” (Jennifer, 09:10)

2. Misunderstanding Size vs. Proportion

[11:49-19:42]

• Problem: Sizing up to fix proportion issues (e.g., to get extra length or fit hips) solves the wrong problem and leads to ill-fitting clothes elsewhere (shoulders, waist, etc.).
• Examples:
  • Long-torso women sizing up shirts for length but ending up with shirts that are baggy elsewhere.
  • Curvy women buying bigger pants to accommodate hips, resulting in “waist gaps.”
  • Petites buying regular sizes and just hemming, resulting in misplaced knees/pockets and ill-fitting garments.
• Advice:
  • Determine your body’s proportions (curvy, petite, tall, etc.) and shop for cuts/designed proportions that match—not just sizes.
  • Quote:

    “The problem wasn’t that the top didn’t fit me, it was that it was too short for my body, the shirt’s proportions didn’t match mine, and by sizing up, I was solving the wrong problem.” (Jennifer, 13:15)

3. Believing Sizes Mean Anything

[19:43-32:33]

• Problem: Assigning personal value to a number/letter on a label or believing you’re the same size everywhere can sabotage your style.
• Pitfalls:
  • Refusing to size up or consider plus sizes due to self-perception.
  • Not believing a smaller size might fit (“I can’t be a small!”), leading to only buying your “regular” size.
  • Assuming consistency within brands/stores (it’s a myth!).
• Advice:
  • See sizes as a starting point, not a definition of self-worth.
  • Use brand knowledge, item descriptions, and reviews to gauge fit.
  • Expect inconsistency between brands/stores (and sometimes within!).
• Thoughts on Vanity Sizing:
  • Yes, sizes have shifted over decades, but this reflects brands catering to their current, average customer—not necessarily to manipulate self-esteem.
• Quote:

  “Stop shopping with your mind mirror because she is a lying liar who lies.” (Jennifer, 24:57)
  “Would it be lovely if sizes were consistent between stores and brands…? Yes. But that’s not the way it works. And you can either spend your time being mad about it and wearing ill-fitting clothes, or accept it and work with it.” (Jennifer, 27:05)

4. Forgetting How Fabric Affects Fit

[32:34-38:27]

• Problem: Not taking fabric properties into account leads to buying the wrong size or ill-fitting pieces.
• Examples:
  • Woven tops (non-stretch) vs. knits (stretch) may require different sizes for the same person.
  • Stretchy fabrics can be problematic—especially knits with high spandex, which cling uncomfortably.
  • Dye can affect denim fit (darker washes tend to be stiffer and tighter than mediums/lights).
• Advice:
  • Select cuts and fabrics that suit your body and preferences, not just your “size.”
  • If it’s clinging or binding, try a different fabric rather than just a bigger size.
• Quote:

  “Every time I try one on it clings and I think, oh, it’s too small, so I’ll just try a bigger size—and you know what? It still kind of clings. That’s just what this fabric does.” (Jennifer, 34:49)

5. Unwillingness to Tailor

[38:28-44:07]

• Problem: Not tailoring “inexpensive” pieces out of a sense they’re not worth the effort or cost leads to a wardrobe full of mediocre, ill-fitting clothes.
• Advice:
  • View tailoring as an investment in your style and self-confidence, not just the garment.
  • The question isn’t “is this piece expensive enough to tailor?” but “does this piece deserve a place in my wardrobe if it doesn’t fit my body?”
• Quote:

  “If you struggle with seeing the value in alterations, try looking at it like tailoring is an investment in you and your style, rather than an investment in the skirt.” (Jennifer, 41:13)

6. Bonus Mistake: Not Knowing What Good Fit Actually Looks Like

[44:08-47:55]

• Problem: Many women’s fit standards are simply “it stays on my body.”
• Advice:
  • Learn what hallmarks of proper fit look like (gapping, drape, pooling, tightness, etc.).
  • Try on multiple sizes intentionally; take store mirror selfies for comparison.
  • Awareness is the first step—once you see good fit, you can’t “unsee” it.
• Quote:

  “Fit is something that’s difficult to see until you see it, but once you see it, you can’t unsee it.” (Jennifer, 45:15)

Notable Quotes

• “If you don’t have fit, you don’t have style.” (Jennifer quoting Stacy & Clinton, 00:01)
• “Sizes are fluid at best, and sometimes even completely meaningless.” (Jennifer, 28:50)
• “Solving the wrong problem—whether it’s cut, proportion, fabric…we think a different size will make things better, and while it might solve one problem, it often causes others.” (Jennifer, 46:22)

Key Timestamps

| Time | Segment | |-----------|---------------------------------------------------| | 00:01 | Introduction to the importance of fit | | 03:19 | Mistake 1: Confusing “fit” with “fit” (size vs cut)| | 11:49 | Mistake 2: Size vs. proportion | | 19:43 | Mistake 3: Believing sizes mean anything | | 32:34 | Mistake 4: Fabric’s impact on fit | | 38:28 | Mistake 5: Reluctance to tailor | | 44:08 | Bonus: Not knowing what good fit looks like | | 46:50 | Recap and actionable steps |

Actionable Takeaways

• Don’t use size as the only tool for achieving the right fit—pay attention to cut, proportion, and fabric.
• Understand and shop for your true body shape and proportions.
• Detach your self-worth from the number on the tag—sizes are brand and even item specific.
• Read clothing descriptions and reviews thoroughly, especially when shopping online.
• Invest in tailoring pieces you love—even inexpensive ones—if they’ll become wardrobe staples.
• Learn what truly good fit looks like, and train your eye to spot when something’s off.
• Regularly assess the fit of your wardrobe and don’t settle for “it stays on my body” as your only standard.

Jennifer’s warm, direct tone and real-life examples will leave you feeling empowered and better equipped to make fit—not size—the cornerstone of your style.