Bonus Giggly Hotline: skinny jeans and starting over

Summary

Giggly Squad — Bonus Giggly Hotline: Skinny Jeans and Starting Over

Hosts: Hannah Berner & Paige DeSorbo
Date: October 30, 2025

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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.

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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.

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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.

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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)

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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
• 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.

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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)

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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)

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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

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Tone & Style

• Conversational, cheeky, supportive, and irreverent.
• Hannah and Paige freely mix solid advice with playful self-deprecation and authentic storytelling.

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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.

Transcript

[A]

Okay. We're so excited to be doing this extra special episode with Depop because we're gonna be answering all of your fashion questions.

[B]

We're gonna be the fashion police.

[A]

I can't wait to see how you interpret it and how I interpret it.

[B]

Interpret it is such a nice word to use. Yeah, I'm on my Depop shit. Like, I'm currently looking at these 90s vintage sunglasses that I need. Oh, that's you. Yeah, they, you know, I don't like.

[A]

When you see them.

[B]

You guys submitted fashion questions. I feel like some might be directed towards you, but I'm gon answer it anyway. Cause I don't care because, like, I'm not gonna let people.

[A]

This is a matriarchy here.

[B]

Yeah. Like, I'm gonna take up space. Yeah. Depop is the home of circular fashion, where taste recognizes taste. I love circular fashion. I love discovering things that aren't just, like, in the stores where people are like, this is what you have to buy.

[A]

You love a challenge.

[B]

I love a challenge.

[A]

You love being creative.

[B]

I love being creative.

[A]

You love making it your own.

[B]

Paige, you look so snatched. What is this top?

[A]

Okay. You picked this out for me, this sweater. It's, like, tight here.

[C]

And then.

[A]

Wait. Actually, I don't know.

[B]

It's Alexander Wang.

[A]

It's Alexander. And I actually do really like it. And then I have these little, like, gray shorts on.

[B]

I'm obsessed with tights, which.

[A]

If I had tights.

[B]

Oh, my God. Just underwear and tights.

[A]

Well, no, I have shorts on. Oh, sorry.

[B]

No, it's your thing.

[A]

And no bottoms.

[B]

And no bottoms. Wait, are we done with the underwear look? Is it over?

[A]

It's definitely not over. Like, I feel like micro shirts are still happening. I just feel like I've done it so much. I did it before people were doing it, so I feel like people are sick of seeing me in it.

[B]

Got it. So you're sitting on the bench for that. Anyway, I'm wearing Lacoste. Wait, it's giving. This is what we'd wear in middle school.

[A]

Yeah. If you had a second one on top of it. And both collars and collars up.

[B]

I'm obsessed with polos for fall and buttoning it up all the way to the top. Trench coat button to the top. There's something about it that, like, it's so not sexy. It's sexy.

[A]

Well, it's kind of like having a tie on without having a tie on.

[B]

That's why I like it.

[A]

You love a tie.

[B]

It's giving, like, accountant who didn't go to college.

[A]

Yeah.

[B]

And let's continue. Hi, Paige and Hannah. My question. Do we prescribe to skinny jeans? Coming back. I know Paige loves a little cigarette that pant Capri vibe, but I'm talking full length skinny jeans. Do we prescribe, yes or no? Because I fear I have thrown them all out. Thank you.

[A]

I don't think she needs them unless she's, like, really trying to do, like, a riding boot and she's tucking them into her riding boot.

[B]

If she has a horse.

[A]

Yeah, well, riding boots are really back.

[B]

Can you tuck, like a regular jean.

[A]

Into a riding boot?

[B]

Into a riding boot.

[A]

You can tuck, like a bootleg jean into a riding boot.

[B]

Okay. Cause I hate skinny jeans, but I do love a high. I don't know any of the terminology, but a high boot with a jean.

[A]

Like a flat boot. No, a high heel boot with like a thigh high. Yeah, yeah.

[B]

No, not up to the thigh. Like just. Just up to the knee over a jean. Oh, yeah, that's.

[A]

No, don't do that.

[B]

Don't do that.

[A]

Aw.

[B]

No, wait, you never put a jean.

[A]

Tucked into a. I did in 2008. Yes. I think it was a great look.

[B]

Okay, 2008 is in.

[A]

We've moved past. I think all of those styles are coming back, but they're a little bit more, like, modernized and elevated.

[B]

It's giving you love saying elevated. Yeah, I do. It's giving girls with their pumpkin spice lattes on the farm. Yeah.

[A]

I think you could do skinny jeans and a thigh high boot and a massive, like, faux fur jacket.

[B]

Love.

[A]

Love that.

[B]

Love, love. I love saying faux fur too. Yeah, Faux fur. Faux fur. I like that laugh.

[A]

That got me so good.

[B]

Okay, Chris, so skinny jeans. Burn em.

[A]

No.

[B]

Oh, wait, I didn't. Was I? You were listening. You said yes. For a riding boot.

[A]

Yeah.

[B]

If you have a horse.

[A]

Yeah.

[B]

Or if you don't have a horse, it's fine. Yes.

[A]

And I think it was a thigh high. Whatever you suggested.

[B]

All the way to the thigh. Not what I suggested. Write it down, guys. Write it down. This is class. Welcome to class.

[C]

You guys, this is a long time coming. I've needed some help with this. I don't care what I look like unless my picture is being taken and I want to. I want to look cute on a daily basis, even if I'm going to a grocery store looking like a tired ass mom. Because honestly, I just have a dog. I don't have any children, but I'm always out here with leggings and sweatpants. So any Tips on how to throw together a cute but comfy outfit. Thank you.

[B]

And I'm going to relay to you on this one. I'm going to pass.

[A]

Why don't you take this one? This seems more up your alley. I would say it all has to do with, like, an outfit formula. Like, a perfect example is when I was, like, peak first dating, like, in my 20s, I would wear the same outfit on every first date because I was like, it's too stressful to figure out a whole new outfit.

[B]

How many dates were you going?

[A]

I had a good algorithm. And so I think it's a. I think it's a outfit formula. So you have to find a pair of pants that are, like, your style, your comfort level, and then literally get them in a couple different colors. So whether it's like a jean or.

[B]

Like a cargo, we can't be doing jean. Going to the store.

[A]

What?

[B]

Jeans going to the store sound. It's, like, uncomfortable.

[A]

What do you want to put her in?

[B]

I love that we're dressing her.

[A]

Barbie, what are you doing?

[B]

Me and you. Me and you having to work as stylists together.

[A]

What are you putting her in?

[B]

I'm like, we're in front of the client right now.

[A]

She said she doesn't want to be in sweats and leggings anymore.

[B]

Okay, well, I would add on. To add on, you need a uniform. I love a track pant.

[A]

Okay.

[B]

Like, I mean, your Daphne one with the lining on the side. I love a line on the side. And then you. What would you add to that?

[A]

Actually, the Daphne pants are very street wear.

[B]

Yeah, See, I love streetwear for the streets.

[A]

Okay, so my outfit formula, when I'm like. Okay, like in the fall, where I'm like, it's a Wednesday afternoon and I'm running out, but I wanna look cute. I wear, like, a straight leg jean, a ballerina flat, a T shirt, and like, some type of cute little jacket.

[B]

Like a trench.

[A]

Could be a trench. Could be like a crop jacket. Could be a crop trench.

[B]

Could be a fauffer crop trench.

[A]

Could be so many different things. Yeah, I think you have to first pick out your shoe. I would suggest working from the bottom up.

[B]

Okay, guys, this is actually class, right now. Write this down. I've never worked bottom up. I've never even considered what my shoes are going to be. My shoes are actually none of my business.

[A]

Because your shoes dictate your pants, not the other way around. What?

[C]

That's just.

[A]

I just made that up. Quote me on it, though. Wait. The other day, I Sent Hannah a voicemail. And I go, listen to this quote by me. Then I go, that wasn't what I thought of. She messed up and I messed it up.

[B]

You know, it's your quote. You can't mess it up.

[A]

Right.

[B]

Do you pick your shoe based on, like, what you're gonna be doing that day or based on, like, what your aesthetic, your vibe is, what my aesthetic is not? Like, if you're walking eight miles, not my business.

[A]

The location, not my business.

[B]

And if you guys don't know this, my favorite all time thing about Paige is that she once told me she can get any shoe size to fit her foot, and that's her special skill.

[A]

You're a Michelin star, chef.

[B]

I fit any shoe size and I've seen it happen.

[A]

It's fucking crazy. If I can wear an eight, sure can. I'm a seven.

[B]

And you could wear like a five, too.

[A]

I've gone 6.6.5.

[B]

And you, like, I've never seen you walk awkwardly. I also haven't seen you walk before. I'm like, oh, she's not walking today. I also, there's something about me where, like, I either am, like, dressed up or I'm dressed down. I don't have an in between. Yeah. So, like. But I do understand what she's saying. I don't think I'm the right person to answer this. However, I do love a street style of, like, get like a cute crew neck hoodie that you like to wear. Put it over a T shirt, have your track pants and like some sneakers.

[A]

What's a crew neck hoodie? Oh, like a crew neck. Like a sweatshirt.

[B]

Yeah, a crew neck sweatshirt that you like over with.

[A]

What pants?

[B]

Track pants.

[A]

Okay. And just like, I'd wear that to, like, the airport.

[B]

What? What you wear to the airport is what I wear day to day.

[A]

Okay, Grace, next question.

[D]

Hi, Hannah. Hi, Paige. Longtime giggler here. I just moved to New York City postgrad from Wisconsin. Go Badgers. But I wanted to know what fashion staples you guys think I need for living in the city now that I'm here. I'm obviously thinking like a ballet flat. A trench coat perhaps? Maybe. Maybe some scarves. But anyways, let me know because obviously the fashion in Madison is quite different than here in New York. So please let me know. Anyways, love you both. Bye.

[B]

So just to give you some color and context, in Madison, there's two types of people, the coasties and the sconies. So the sconies are people from Wisconsin. They call themselves sconies.

[A]

Okay.

[B]

They're locals and they. They all grew up with like everyone being very similar. So, like, they all kind of wear the same things.

[A]

North Face.

[B]

So that is actually what the Coasties wear.

[A]

Okay.

[B]

Because that's like the Long island girls who come in. So they're wearing all the Uggs and the North Face. I feel like you don't want to dress like everyone else's dressing. I think you take little things that you like.

[A]

Little mods.

[B]

Yes.

[A]

Which is why Depop is perfect. Especially if you are moving from somewhere else. Because I feel like it could be overwhelming. She's probably like, I need a whole new wardrobe. I live in New York City now. Yeah.

[B]

And you don't just want to like go to a big brand store and buy what everyone. And spend a ton of money buying what everyone's going to be wearing. You don't want people to be like, I just got that.

[A]

Yeah.

[B]

Like you want to find stuff on depop.

[A]

I think where she should start is because it is starting to get cold coats. I feel like living in New York City is all about your coat.

[B]

True. I didn't realize that till very recently. And even if my outfit was cute, I'd ruin it because I'd have my coat on.

[A]

So I would say like three really good coats that you are gonna wear every day. So like a longer trench. I would say like a cropped like wool Jack. Like an easy throw on wool jacket. And then not even like this isn't even like fashion wise. You need like a really good winter coat.

[B]

Yeah. You need like, like a Fluffy.

[A]

Yeah.

[B]

Like inhale. You'll be okay.

[A]

Yeah. But I feel like one needs to be a trench. It could even be like a leather trench. One needs to be like a cropped cute warmer Jack. Then your full on winter coat.

[B]

I would also argue have some fun with sunglasses.

[A]

I kind of live by the rule that if you have your hair and makeup done, your outfit doesn't matter. And if your outfit is bad, you have to do your hair and makeup.

[B]

So get glam.

[A]

Yeah. And also get glam.

[B]

I think you should take the first week, go to the park, go on the subway.

[A]

Wait, this is actually really good idea.

[B]

Sit on a brownstone and just people watch. And this is where you go. Okay. I feel like that's too far for me. That's right. And try out some stuff.

[A]

And it's very like, I feel like that's the best for what are the shoes that everyone's wearing? Like, everyone's in loafers, everyone's in ballet flats. Also, like, you need a good leather jacket for New York City.

[B]

You do need a good leather jacket.

[A]

Depop is really good for leather jackets because, like, 90s Levis, lavivis 90s leather jackets are really in. I feel like you can get a lot more of them on Depop than like, a new one.

[B]

Also, if you don't want to go to therapy, just go through all of your clothes. Like, 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 in your life.

[A]

There's nothing I love more than organizing it. Organizing and being able to then sell on depop. It's almost like the organizing isn't as bad. Cause you're like, oh, I'm making money. I'm making money doing this.

[B]

Yeah. Cause if you're like, oh, I kind of want to keep it, but if you haven't worn it, if you haven't touched it, if you don't see yourself going outside of New York with it, sell them, because someone will love it. There's also no seller fees on depop. And as women in stem, like, that's important. We love having multiple sources of income because you never know. You never know when you need it, you never know when you got fired.

[A]

And then once you've gotten rid of stuff, you can make these kind of like mood boards on depop. And you love a mood board. Get me started on a mood board.

[B]

I love it because I'm a visual learner.

[A]

And then you can, like, put outfits together and like, see how they look.

[B]

It's their new outfits feature. And you can share it with friends and you can, like, shop the mood board, which is so fun. Cause one thing about me is I.

[A]

Love a project and that's like, nice. Like, hey, what are you wearing tonight? And you just like, send your mood board.

[B]

Oh, my God. I know you're going out. And it's like, we need a theme or we need to be like, matching to some extent or like, does this work? And instead of having to do that awkward mirror pic, you just send them a Depop outfit.

[C]

Hi, Paige.

[A]

Hi, Hannah.

[C]

So I live in New York City, and every fall I struggle with finding cute going out outfits. It's getting cold out, so I need to wear a jacket. And last season I found myself, like, rotating over the same three leather jackets. So my question is, like, what are the girls wearing when we go out to the club? Or just like a dive bar? Something suitable, but will also keep me warm.

[B]

So there's two things going on here. First of all, are you risking that you are going to take your jacket off and you will get it stolen or lost? So that's a factor you have to factor in. Or are you saying it, I'd rather be freezing and not ruin my outfit with a coat. Or are you wearing a nice coat, going out and paying the valet guy to hold your coat check? Coat check.

[A]

Everywhere you go has code check in New York.

[B]

I feel like, okay. But, yes, this is why we're going.

[A]

Is there a time where, like, you get the wrong jacket back? Like, that's only happened to me, though, like, truly once, so I don't wear that.

[B]

Did you upgrade?

[A]

I can't remember. I think it was, like, a Zara leather jacket.

[B]

What coats are you wearing?

[A]

Like, out?

[B]

Yeah.

[A]

Okay. If you want to wear a jacket and you're like, I don't care if this gets taken or I forget it, I always think, like, a black, oversized blazer. Just, like, always goes with everything. Whether you're wearing, like, a skirt and boots or you're wearing, like, leather pants, like, it just always goes. I feel like leather jackets in the winter don't really keep you that warm, so I really don't gravitate towards them. I'm in my 30s, though. Like, I'm never not wearing a coat out when it's cold.

[B]

Yeah, the good old days are over.

[A]

Yeah.

[B]

When I. That one guy gave me his coat and then he asked for it back in Madison, that was my villain origin story.

[A]

Like a big le trench, I feel like is in with, like, shoulder pads and then, like, a big faux fur. Like, whether shoulder.

[B]

I was gonna say, I love a faux fur.

[A]

Yeah, Everyone wears fur in New York because it's so cool.

[B]

Black faux fur is perfect.

[A]

Thank you, Depop, for making this bonus hotline episode possible. We are obsessed with you guys.

[B]

I also feel like I learned so much. That was really good.

[A]

That was a TED Talk.

[B]

That was a TED Talk.

[A]

And you can ask us anything about fashion at giggly style hotline.com Paige has.

[B]

A lot more info to give. As for advice about building a closet, holiday parties, anything about our personal fashion styles. Anything about me? If you want to know, just submit questions. We can't wait to hear from you guys. Gig Squad hotline.