Giggly Squad — Bonus Giggly Hotline: Skinny Jeans and Starting Over
Hosts: Hannah Berner & Paige DeSorbo
Date: October 30, 2025
Overview
In this lively bonus episode, Hannah and Paige team up with Depop to take on listeners’ fashion dilemmas with their trademark banter and honesty. The theme centers around evolving style, from the controversy of skinny jeans, to creating easy everyday looks, and navigating fashion life in New York City. With their mix of practical advice and tongue-in-cheek commentary, the duo emphasize creativity, individuality, and not taking trends (or yourself) too seriously.
Key Discussion Points & Insights
1. Circular Fashion & Individual Style (00:00–01:55)
- Paige and Hannah share their love for Depop and the thrill of discovering unique, non-mainstream pieces.
- Memorable Quote:
“Depop is the home of circular fashion, where taste recognizes taste.” — Paige (00:37) - Appreciation for the creativity and challenge of making styles your own.
- Paige discusses her current outfit (an Alexander Wang sweater and shorts), with both hosts riffing on how style can be playful and personal.
2. Skinny Jeans: Should They Come Back? (02:07–04:23)
- Listener asks if skinny jeans are making a comeback and if she needs to repurchase.
- Key Take: Both hosts agree that unless you’re intentionally styling them with riding boots or for a specific look, there’s not much need to rush back to skinny jeans.
- Hannah:
“I don’t think she needs them unless she’s really trying to do, like, a riding boot and she’s tucking them into her riding boot.” (02:35) - Banter:
- Paige jokes, “If she has a horse…” (02:42)
- Both reminisce (with mock horror) about 2008’s tucking jeans into boots trend.
- Skinny jeans can work when “modernized and elevated,” for example:
- “Skinny jeans and a thigh high boot and a massive, like, faux fur jacket.” — Hannah (03:49)
Consensus:
- Only hang onto or buy skinny jeans if you’re planning a specific throwback vibe or practical pairing. Otherwise, let them go.
3. Upgrading Everyday Outfits: Comfy Yet Cute (04:27–08:48)
- Listener dilemma: Wants to look cute daily, not just comfy (i.e., tired mom mode in leggings and sweats).
- Hannah & Paige’s Approach:
- Establish an “outfit formula”—find a flattering pant in a few colors for mix-and-match ease.
- Paige champions the track pant with side stripes for street style that's both current and comfy.
- Hannah outlines her formula for fall: straight leg jeans, ballerina flats, a tee, and a statement jacket.
- Shoe-first dressing:
“Your shoes dictate your pants, not the other way around. Quote me on it, though.” — Hannah (07:08) - Paige shares her quirky talent:
“My shoes are actually none of my business.” (07:00)
She claims she can fit almost any shoe size (07:51), which Hannah finds both “fucking crazy” and iconic.
- For streetwear, pair a crew neck sweatshirt with track pants, comfy sneakers.
- Paige sums up her style:
“What you wear to the airport is what I wear day to day.” (08:45)
4. Wardrobe Essentials for NYC Transplants (08:51–13:18)
- A listener just moved from Wisconsin to NYC and asks for staple city pieces.
- Cultural Color:
Paige explains “coasties” (out-of-state, often high-label) vs. “sconies” (locals) at UW-Madison (09:24). - NYC Staples According to Hannah & Paige:
- Three crucial coats:
- Long trench (leather, classic, or faux)
- Cropped wool jacket
- True winter coat (“You need like, like a Fluffy... you’ll be okay.” — Paige, 10:58)
- Fun sunglasses (11:10)
- Good leather jacket, ideally vintage/90s (11:54)
- Loafers and ballet flats for shoes
- Three crucial coats:
- Emphasis on buying selectively and individually:
- Avoid the mass-market trap, opt for unique finds on Depop.
- “When you get out of college, you have to rebrand. Like, you’re not that girl anymore. Purge your clothes and see how light you’re gonna feel...” — Paige (12:07)
- Use Depop’s new “mood board” (outfits feature) to visualize and organize new looks.
5. Fall & Winter Going-Out Looks: The Coat Conundrum (13:30–15:32)
- NYC listener struggles with staying warm but stylish at night.
- Real Talk:
Paige outlines the classic club dilemma:- Freeze and kill the look?
- Wear a coat and pay for coat check?
- Risk losing a cheap jacket?
“Everywhere you go has coat check in New York.” — Paige (14:18)
- Hannah’s picks for outerwear: Black oversized blazer (“just always goes with everything” — Hannah, 14:41), cropped jackets.
- Both agree:
- Leather jackets aren’t warm enough for winter nights
- Big trench with faux fur is on-trend
- “Black faux fur is perfect.” — Paige (15:29)
Notable Quotes & Memorable Moments
- “This is a matriarchy here.” — Hannah (00:35), setting a playful, inclusive tone.
- “It's giving accountant who didn’t go to college.” — Paige, on buttoned-up polos and fall fashion (02:03)
- “My shoes are actually none of my business.” — Paige (07:00)
- “If you don’t want to go to therapy, just go through all your clothes.” — Paige (12:07)
- “When you get out of college, you have to rebrand. Like, you’re not that girl anymore.” — Paige (12:07)
- “What you wear to the airport is what I wear day to day.” — Paige (08:45)
- “Your shoes dictate your pants, not the other way around.” — Hannah (07:08)
Timestamps for Key Segments
- [00:00–01:55] – Intro to Depop & personal style
- [02:07–04:23] – Skinny jeans: To keep or not to keep?
- [04:27–08:48] – How to dress cute and comfy every day
- [08:51–13:18] – Must-have wardrobe items for new New Yorkers
- [13:30–15:32] – Staying stylish (and warm) for nights out
Tone & Style
- Conversational, cheeky, supportive, and irreverent.
- Hannah and Paige freely mix solid advice with playful self-deprecation and authentic storytelling.
Final Thoughts
This energetic episode underscores that style doesn’t have to be stressful or prescriptive. Whether you’re considering resurrecting skinny jeans, revamping your closet post-move, or just aiming not to look “tired” at the grocery store, Hannah and Paige’s advice is: find your own formula, don’t fear standing out, and, most importantly, have fun with fashion.