Giggly Squad – Bonus Giggly Hotline: Stirrups, Shoes, and Stress

Hosts: Hannah Berner & Paige DeSorbo
Date: November 20, 2025

Episode Overview

In this special "Giggly Hotline" bonus episode, Hannah and Paige answer listener-submitted fashion questions, diving into topics ranging from the resurgence of suiting and menswear-inspired trends to the right way to wear stirrup leggings and the reemergence of peep-toe shoes. The conversation is light-hearted and playful, featuring plenty of banter, personalized style advice, and the duo’s trademark wit. Their discussions highlight current trends, body type considerations, and fashion faux pas, all while stressing the fun and personalization of style—and, of course, a recurring plug for Depop, the circular fashion app.

Key Discussion Points & Insights

1. Menswear as Womenswear: How to Make It Work

• Listener Q: "How are the fashion girlies hopping on the menswear-as-womenswear trend? How do I make it a fit?" (01:55)
• Paige's Take: Oversized blazers—especially matched with oversized or more fitted pants, like cigarette or leather capris—are the way to go right now. YSL is hailed as the expert of runway suiting. She wore leather capris with an oversized blazer to dinner recently, paired with a kitten heel. (03:08)
  • Memorable quote: “I did ties first. It was a Valentino tie. I wore it with a Valentino skirt. Bravocon. Two years ago. Fuck it.” – Paige (02:31)
• Hannah’s Advice: Oversized is key—“I like to show my waist, cause I could look very squarish. So I like to add a belt to an overflow blazer. But remember, belts, like, five years were, like, not good. Like, five years ago, if you wore a belt, it was like, cheugy. Where now belts are so in.” (03:56)

2. Tips for Styling Workwear & Runway Trends

• Paige: Adds that pencil skirts are back, especially paired with oversized blazers and long leather gloves. Layering a sweater over a blazer, or slinging it over the shoulders for a “preppy generational wealth” vibe, are recommended. (04:30)
  • Hair can feminize a masculine look—try a “Pamela updo” or tousled waves. (05:17)

3. Men’s Fashion: What Women Want

• Listener Q: What do you need the men in your life to wear to ‘elevate’ and complement your looks? (05:35)
• Paige & Hannah’s Preferences:
  • Paige: Above all, vulnerability. “What am I a big fan of that men wear? Vulnerability.” (06:05)
  • Both love pants and a cable knit sweater for men—"All I want is my man to wear pants and a cable knit sweater. He's perfect." – Hannah (05:57)
  • Paige suggests bombers; Hannah disagrees, thinking they can be try-hard unless worn by gay men. (06:13)
  • Rugby shirts with updated fits and cardigans are recommended by Paige. Layering with scarves is fun, especially for gay men—Paige jokes, “I hate when a straight man does a scarf. Yeah, yeah. I'm like, you're probably going to strangle someone with that.” (07:20)
  • Leather jackets: Hannah is cautious (“Are you weary of a leather jacket because you're afraid they'll just go full Danny Zuko?”), Paige thinks they carry “too much power.” (07:44)

4. Stirrup Leggings: Chic or “Horse Girl”?

• Listener Q: Are stirrup leggings chic, and how should I style them? (08:02)
• Paige explains that these leggings hook under the foot and are best with ballet flats or kitten heels rather than full pumps to avoid an overly 80s vibe. (08:37)
• Hannah on color: "If I did, like, a green, I would look like Peter Pan." (09:42)
• Styling advice: Go all black for safety, treat them as regular leggings, and pair with an oversized sweater or a cropped/waist-length jacket. Stirrup leggings, they note, are a perfect trend to buy secondhand on Depop. (09:41)

5. Peep Toe Shoes: Back in Style?

• Listener Q: Are peep toe shoes coming back? Are we wearing them to the office? (11:18)
• Paige’s verdict: Peep toes are back and best for summer—especially with stirrup leggings. Admits they are “more of a summer shoe” and would hesitate on office wear unless the environment is casual. (11:57)
  • Memorable quote: "Peep toes are so back and I'm so here for it." – Paige (11:38)
• Hannah agrees with the allure: “I’m a little bit of a prude. Like, let's start slow with little peep toe. I like that.” (12:22)

6. Complimenting & Community Etiquette

• Hannah’s anecdote: After complimenting a girl on her flare pants in Soho and receiving a flat “thanks,” Hannah jokes she might never compliment again. Provides a window into their expectation of female camaraderie: “If a girl doesn't look at me and say, ‘Oh, my God, thank you. That's the nicest thing you ever said,’…then now I'm like, I’m gonna fight with this girl.” (13:13)

7. Casual Recommendations & Depop Endorsement

• Sourcing trendy pieces: Both recommend Depop for acquiring and reselling statement trend pieces—ideal for those cycling out, like stirrup leggings and fresh sweaters each winter. “Depop is perfect for a stirrup.” (09:20)
• No seller fees: Hannah highlights the app’s ease and lack of seller fees. (11:05)
  • Memorable quote: “One of my favorite things about Depop is, like, it's winter, so, you know, there's like, a couple things that you're like, wow, I need all new sweaters. I need all new, like, jackets. But Depop has such a good selection…” – Paige (10:23)

Notable Quotes & Memorable Moments

• “You can rely on [buttons] much more than a man. They're not gonna lie to you… They do what they say they will.” – Paige & Hannah on fashion’s dependability (00:57)
• "I'm bottom heavy. You're just not heavy. So I like to show my waist. Cause I could look very squarish." – Hannah, discussing how body shape affects suiting (03:56)
• “All I want is my man to wear pants and a cable knit sweater. He's perfect.” – Hannah (05:57)
• "[Men's] vulnerability. Listening. Ears." – Paige & Hannah, joking about what really makes a man stylish (06:05)
• "I hate when a straight man does a scarf. Yeah, yeah. I'm like, you're probably going to strangle someone with that." – Paige (07:20)
• "If I did, like, a green, I would look like Peter Pan." – Hannah on stirrup leggings (09:42)
• "Peep toes are so back and I'm so here for it." – Paige (11:38)
• “I love a gay man in a turtleneck. I don't like a straight man in a turtleneck. And I will not be explaining further.” – Hannah (10:57)
• “If a girl doesn't look at me and say, ‘Oh, my God, thank you. That's the nicest thing you ever said…’ now I'm like, I’m gonna fight with this girl.” – Hannah (13:13)

Timestamps for Key Segments

• Depop & Current Fashion Finds: 00:00–01:45
• Menswear/Womenswear Q&A: 01:52–05:30
• Men’s Outfits & Preferences: 05:35–07:58
• Stirrup Leggings Trend: 08:02–10:21
• Seasonal Shopping on Depop: 10:23–11:17
• Peep Toe Shoes Trend: 11:18–12:53
• Compliment Etiquette Story: 12:53–13:32

Tone & Delivery

The episode is lively and irreverent, combining actionable fashion advice with sarcastic quips and playful self-deprecation. Hannah and Paige rarely miss an opportunity for a joke, but still provide thoughtful answers rooted in personal taste, style experimentation, and current trends. Their chemistry keeps the conversation fast-paced and relatable, making the hotline format feel like friends chatting with friends.

For listeners seeking style inspiration, trend validation, or a genuine laugh about the “logic” behind scarves and the existential drama of complimenting strangers, this episode is quintessential Giggly Squad: equal parts practical and hilarious.