Podcast Summary: would you rather, fashion edition
anything goes with emma chamberlain
Host: Emma Chamberlain
Date: September 25, 2025
Episode Overview
Emma Chamberlain dives into a fun, introspective game of "Would You Rather: Fashion Edition." Recorded, as always, in her signature intimate style, Emma challenges herself with a series of hypothetical (and often harrowing) sartorial dilemmas. From choosing between black-and-white outfits or colorful wardrobes to picking between glasses and makeup, Emma unpacks each scenario with humor, tons of personal anecdotes, and her trademark over-analysis. The episode offers a glimpse into Emma's evolving fashion philosophy, her penchant for comfort vs. aesthetics, and the deeper psychological connections she has with style.
Key Discussion Points & Insights
Only Black & White Outfits vs. Only Bright, Colorful Outfits
[02:10 – 07:20]
- Emma is currently deep into a black-and-white/neutral phase but admits her tastes change unpredictably.
- She feels chic and confident in black and white, stating,
"There's something about wearing black that makes me feel so chic...every time I put on an all-black outfit or a black and white outfit, I'm like, wow, this is fashion. This is chic." (Emma, 04:08)
- Bright colors currently make her feel "unrefined" and less confident.
- Acknowledges uncertainty about the future of her taste but concludes:
"Right now, I feel so much more confident in black and white that it almost is incomprehensible to me that wearing bright colors could ever make me feel more confident." (Emma, 05:25)
- Final decision: Black & white outfits.
Wear the Same Outfit Every Day vs. Never Repeat an Outfit Again
[08:00 – 16:10]
- Emma enjoys mixing up her wardrobe but has grown to appreciate re-wearing favorite looks.
- The concept of one outfit forever is "a little bit depressing," mainly due to missing the ritual of dressing up.
- She admits overthinking outfits can sometimes be "exhausting," and removing choice may be freeing:
"There are times when I don't want to leave the house because my outfit isn't good enough yet. That's kind of stressful." (Emma, 13:55)
- Ultimately chooses never to repeat an outfit, even though it would be "financially irresponsible" and "exhausting." She’d rather sacrifice comfort than self-expression:
"Because I do like dressing for an occasion ... I think I'm gonna choose that over wearing the same outfit every day because I would really miss the experience of getting to play with fashion on myself." (Emma, 12:35)
Coachella Every Day vs. Paris Fashion Week Every Day
[17:10 – 26:40]
- Emma reminisces about both her over-the-top and more casual Coachella looks—most of which she now cringes at.
"Even still…I'll put together an outfit for Coachella that I would never wear outside of Coachella because the dress code is different. But then I look back at it later…and I'm like, ooh, what was that? ... cringe to me now for some reason." (Emma, 20:10)
- Paris Fashion Week style is more "refined," "avant-garde," and represents Emma’s style best but is "incredibly uncomfortable."
- Memorable story: Wore size 9 boots (she’s a 6.5–7!) because that’s all a brand had:
"And I did almost trip many times, but I survived and I did not trip. So that was good." (Emma, 23:28)
- Final answer: Paris Fashion Week vibes, despite the discomfort, as it better expresses herself.
Heels Every Day vs. Sweatpants Every Day
[33:27 – 39:10]
- Emma used to be a sweatpants girl but now feels un-put-together when wearing them.
- She struggles with severe foot pain in heels but loves how they look, especially lower heels.
"I actually really love how a heel looks. I wear heels to every single fashion event I attend, pretty much because I like the way that they look. I do. But I hate the way that they feel." (Emma, 37:15)
- Sophie’s Choice: Will wear heels—assuming she can pick the height—so she can avoid the "mentally bummer" consequence of living in sweatpants.
Never Wear Glasses Again vs. Never Wear Makeup Again
[40:40 – 48:40]
- Struggles deeply with this one—Emma considers glasses central to her look and even "social armor":
"I cannot leave the house. I also feel like, too, they weirdly help me socially. Like, I feel like when I have glasses on, it protects me socially. Like, I feel naked without glasses on." (Emma, 42:48)
- Loves makeup as "an extra extension of my outfit."
- After much internal wrestling, chooses glasses—mainly for their functional element and how integral they are to her day-to-day style.
No Layers vs. No Accessories
[49:50 – 55:20]
- Layering basics is her “visual interest” hack, but accessories (purses, glasses, jewelry, belts) are far more essential.
- Cites their functionality and ability to “serve a purpose” vs. layering, which is more just for looks.
- Decision: Gives up layering to keep accessories.
Tiny Micro Bag That Fits Nothing vs. Giant Heavy Tote Bag
[56:00 – 58:44]
- Despises tiny bags ("waste of hand space"), but is not a fan of being physically burdened by heavy totes.
- Strategic loophole: Choose the micro bag but “just put everything in my pockets” and stuff the tiny bag in her back pocket.
Clothes Always One Size Too Big vs. One Size Too Small
[59:15 – 01:05:15]
- Hates too-tight clothing: “Clothes that are too small almost never look good.”
- Oversized can be cute “at least 30% of the time.”
"I also just love loose clothes. Oh, my God. I love loose clothes." (Emma, 01:01:30)
- Picks one size too big—more comfortable and versatile.
Fashion Inspo: Pinterest 2012 vs. TikTok 2020 Trends
[01:05:39 – 01:09:29]
- Roasts 2012 Pinterest era: “It was the worst era of fashion. End of story. I don't think there's any...it couldn't have been uglier. It truly couldn't have.”
- TikTok 2020 had Y2K, upcycling, pattern play, claw clips—“more options.”
- Picks: TikTok 2020 trends.
Athletic/Athleisure Only vs. Formal Only
[01:10:10 – 01:13:20]
- Gut says formal.
- She values looking “put-together” as she gets older and finds formalwear can be comfortable if done right.
- Activewear is functional, but she dislikes wearing it unless exercising.
Shop In-Store Only vs. Only Online
[01:13:21 – 01:17:18]
- Passionate about the tactile, IRL experience of shopping ("more fulfilling").
- Acknowledges the convenience and options online, but picks shopping in-store only.
“There is something to be said for the experience of going out in the world, touching things, talking to people...” (Emma, 01:16:03)
Show Up in the Exact Same Outfit as Someone Else vs. Be Completely Off Dress Code
[01:17:20 – 01:19:34]
- Wouldn't mind twinning—"It's a fun conversation starter."
- Hates standing out for being too casual or overdressed.
- Chooses: Outfit twin over dress code mismatch.
People Call Your Style "Boring" vs. "Too Much"
[01:19:34 – 01:22:45]
- These days, Emma is told her style is boring due to neutral, classic palettes.
- Would rather be called "too much"—"Too much just insinuates that it’s experimental...I think that can be the vibe sometimes."
- "Never want to be thought of as boring in any capacity. That sucks more." (Emma, 01:22:01)
Red Carpet in Outrageous, Memorable Outfit vs. Safe, Forgettable Look
[01:22:46 – 01:25:55]
- Torn between “publicist brain” (outrageous is good PR, people talk!) vs. her personal anxiety from being scrutinized.
- Ultimately:
"I'd rather wear whatever outfit I feel more confident in. If I feel more confident in the outrageous one, I'd rather wear that...If I feel more confident in the safe one, I'd rather wear the safe one..." (Emma, 01:25:10)
Never Cut Hair Again vs. Never Dye Hair Again
[01:25:55 – 01:27:14]
- Loves her short hair too much—would "rather never dye my hair again."
- Feels self-expression comes more from haircut than color.
Never Wear Skirts Again vs. Never Wear Pants Again
[01:27:14 – 01:29:16]
- Loves both, but pants win for comfort, practicality, and more options.
- Will miss skirts—especially "mid-calf" lengths—but
"I can like do a high kick in a pant and I can't do that in a skirt. Cause somebody would see my butthole." (Emma, 01:28:39)
Notable Quotes & Memorable Moments
-
On black and white outfits:
"There's just something so refined about it and so classic about it and so chic and so sharp about it…" (04:48) -
On never repeating an outfit:
"There's nothing I love more than picking out a really good outfit and then re wearing it for like, six months straight until I get sick of it…" (15:05) -
On Coachella fashion:
"The fashion rules at a music festival…are so different from the fashion rules in the real world. Like, at Coachella, you can just wear a bikini top around. You can wear tiny little booty shorts with your butthole out…" (19:25) -
On the importance of glasses:
"The face is really the focal point of every look. Right?...adding accessories to the head, to the face can add so much to an outfit, even though they're small little details…" (41:59) -
On the experience of shopping in person versus online:
"I do think getting out in the world is always going to be better than doing something virtually, because the real world and our participation in it is so important." (01:16:30) -
On pants vs. skirts:
"I can like do a high kick in a pant and I can't do that in a skirt. Cause somebody would see my butthole." (01:28:39)
Timestamps for Important Segments
- Black & White vs. Colorful: 02:10–07:20
- Same Outfit vs. Never Repeat: 08:00–16:10
- Coachella vs. Paris Fashion Week: 17:10–26:40
- Heels vs. Sweatpants: 33:27–39:10
- Glasses vs. Makeup: 40:40–48:40
- No Layers vs. No Accessories: 49:50–55:20
- Micro Bag vs. Tote: 56:00–58:44
- Clothes Too Big vs. Too Small: 59:15–01:05:15
- Pinterest 2012 vs. TikTok 2020: 01:05:39–01:09:29
- Athleisure vs. Formal: 01:10:10–01:13:20
- Shop In-Store vs. Online: 01:13:21–01:17:18
- Twinning vs. Off Dress Code: 01:17:20–01:19:34
- Being Called Boring vs. Too Much: 01:19:34–01:22:45
- Outrageous vs. Forgettable Red Carpet: 01:22:46–01:25:55
- Never Cut vs. Never Dye Hair: 01:25:55–01:27:14
- Never Skirts vs. Never Pants: 01:27:14–01:29:16
Tone & Closing
Emma strikes a playful, confessional, sometimes self-deprecating tone, peppering her answers with personal stories, a little bit of gentle self-psychoanalysis, and a lot of humor. Her reflections reveal an ongoing evolution in her approach to fashion—balancing comfort, authenticity, and fun. The "Would You Rather" framework lets her explore how her style history shapes her preferences, and each answer comes with thoughtful explanations and witty asides.
Closing:
Emma wraps up the episode declaring her love for games, the joy the episode brought her, and inviting listeners to tune in for more Anything Goes—sometimes games, sometimes advice, sometimes philosophical rambles.
"I'm just a silly girl who likes to play games. And so to get to play a game with you today was an absolute joy." (01:29:26)
End of summary.