The 5 Style Phases Every Woman Goes Through, According to Issa Dee

I spent the weekend doing what every bored millennial does when life feels a little too routine—binge-watching a show I’ve already seen. This time, it was Insecure. And let me tell you, rewatching every single episode just confirmed what I already knew: that show is that girl.

Issa Dee, the 20-something California native at the center of it all, was a beautiful mess in the best way possible. Her job situation? Chaotic. Her love life with Lawrence? A rollercoaster. And don’t even get me started on her wardrobe—because that’s what really caught my eye this time around. 

And of course, me being me, I couldn’t help but overthink it a little. Because Issa’s style? Was a timeline and a  reflection of exactly where she was in life—messy moments, glow-ups, and all.

So in this article, we’re breaking down the 5 style phases that we all go through at some point, using Issa Dee as our case study. Watching the show I was able to break down the various phases of Issa’s style that goes hand in hand with her current life.

• Phase 1: The “I’m Just Here Trying to Figure Ish Out” Phase

• Phase 2: The “I’m Just Getting By” Phase (Issa definitely hit her breaking point here)

• Phase 3: The “Main Character Energy” Phase

• Phase 4: The “Soft Life, Strong Outfits” Phase

• Phase 5: The “This Is Me” Phase

Phase 1: The “I’m Just Here Trying to Figure It Out” Phase

Photo:HBO

Let’s take it back to Season 1 Issa. She’s working at “We Got Y’all,” trying to be the voice of reason and inclusion in a room full of awkward silence and tone-deaf coworkers. Her relationship with Lawrence? A mess. No real communication, no clear direction—just vibes and unspoken resentment. She’s working, he’s Lawrencing, and her friends always seem like they’ve got their lives (and their edges) together while she’s still trying to decide what to eat for dinner.

And her wardrobe? Just as lost as she felt. Chaotic prints, overwhelming  colors, random layering—everything looked like it was trying too hard to say, “I’m fine!” when we all knew she wasn’t. Even her apartment felt like a patchwork of hand-me-downs, thrifted finds, and stuff that used to be cute in college.

But here’s the thing: how many of us have been in that phase? Or are still in it?

Looking back at old pictures of me during that time, all I can say is: girl, what were you wearing… and why were you with him? My closet was stuffed with thrift store finds, Forever 21 impulse buys, and clearance rack chaos. Nothing I owned actually matched my goals—but it did match the internal chaos I was carrying.

This is the figuring-it-out stage. It’s less about style and really more about survival. You’re trying things. You’re making mistakes. You’re becoming. And style? It’s not coming from some perfect Pinterest board—it’s coming from your life.

Phase 2: The “I’m Just Getting By” Phase

Photo Credit: HBO

This is the breaking point phase. You’re not spiraling… but also, maybe you are.

For Issa, this was when she finally moved out of the apartment she shared with Lawrence (aka the awkward silence headquarters) and started staying with Daniel. Yes, Daniel—the fine musician who was basically the human version of unfinished business. She was couch-hopping, soul-searching, and trying to piece herself together in the middle of chaos. Still working at “We Got Y’all,” still exhausted by her job, and now single, semi-homeless, and way too aware of how stuck she felt.

But this phase? This is when things started  shifting.

Her style was still a little all over the place, but now it had a little fire behind it. She wasn’t trying to play it safe anymore—because safe clearly wasn’t working. This is the season of becoming. You’re realizing things. Your tolerance for B.S. is lower. You’re shedding old identities, and while you might still be showing up in the same outfits, the woman in them is starting to change.

Your wardrobe’s still in that in-between zone—random pieces from old shopping sprees, a few attempts at “adulting” with structured pieces that don’t quite fit your life yet, and maybe a baddie dress you bought for a night out that you never went to.

This is the “I’m not who I was… but I’m not quite sure who I’m becoming either” era. And whew, it's a ride.

Phase 3: The “Main Character Energy” Phase

Photo Credit:HBO

Issa was outside, okay? This is the Season 3 glow-up we all remember. New energy. New opportunities. New hair. And her wardrobe? Finally catching up to the woman she was becoming.

This is the season where Issa finally had her own apartment. Okay yes—it wasn’t fancy. It wasn’t Pinterest-worthy. But it was hers. No more crashing at Daniel’s, no more awkward co-living tension—it was her space, her rules, her air mattress (we’ve all been there).

She also finally said goodbye to “We Got Y’all,” because mentally clocking out wasn’t enough—she was ready to walk away from the performative allyship, the tokenism, and the energy drain. That alone was a power move. Combine that with the iconic Coachella episode (yes, the one where Molly had us crying and Issa had us rolling), and it became clear—she wasn’t just surviving anymore. She was building something.

This is also when the vision for The Blocc—her community event—was born. She didn’t know exactly how it would happen, but she felt it. She was ready to create something real, and you could feel that in her energy... and her outfits.

Gone were the chaotic prints and forever-in-limbo looks. Issa started dressing with confidence—even if the confidence hadn’t fully caught up yet.Everything became more intentional from the way she mixed her loud chatoric prints with colors that literally made her skin glow. This was the beginning of Issa  owning it.

This phase is where a lot of us start to step into our own power. You’re not quite where you want to be, but you finally believe you can get there. Your style shifts—not because someone told you what to wear, but because you’re finally dressing for who you’re becoming, not who you’ve been.

You're walking taller. You're making decisions. You're dreaming bigger. And your clothes? They’re starting to reflect that.

Phase 4: The Grown Woman Pivot

Photo Credit: HBO

This is the phase where things start clicking. You're not reinventing yourself every week—you’re finally starting to feel settled, even if life still has a few curveballs.

For Issa in Season 4, this was that grown woman pivot we all felt.

This phase looks like finally buying jeans that actually fit—not just squeezing into what’s on sale. You’re not throwing on random pieces hoping for the best. You’re choosing outfits that feel comfortable and put-together. You’re wearing things you can move in, breathe in, and still feel stylish. ”

But here’s the other part of this phase: emotional clarity. And sometimes that means letting go of people you never thought you’d outgrow. That was Issa and Molly.

Their friendship cracked under the pressure of growth. Molly was used to Issa being in a place of confusion, needing advice, needing help. But now Issa was making her own decisions, setting boundaries, finding her flow. And Molly couldn’t handle it. That “friend drift” was one of the most relatable parts of Season 4—and if you’ve ever lost someone close to you during your glow-up, you know exactly what that felt like.

Phase 4 isn’t loud. It’s not about leveling up for attention—it’s about leveling up for yourself. You stop shopping to escape. You stop venting just to fill silence. You start dressing in a way that supports your peace, and building a life that feels aligned.

So if you’re finally saying no without guilt, cleaning out your closet with intention, and realizing that some people can't come with you to the next version of your life—you’re in Phase 4. And you’re doing just fine.

And can we talk about how Issa stopped rapping in the mirror as much during this phase? Like… the freestyles dried up. That was her coping mechanism! In the earlier seasons, she’d be in the mirror spitting full mixtapes to hype herself up or work through whatever awkwardness life was throwing her way. But in Season 4? Not so much.

Once things got real—falling out with Molly, chasing a dream that felt scary, losing people she thought would always be there—she didn’t have the same space for that inner hype girl. And honestly? That silence said a lot. Because when you're healing, sometimes even your go-to ways of processing life start to shift.

So if you’ve noticed you don’t vent in the same way, don’t reach for the same distractions, or don’t need to hype yourself up in the mirror every five minutes just to survive the day—you’re probably in Phase 4. Growth is quiet sometimes. And that’s okay.

Phase 5: The “This Is Me” Phase

Photo Credit:Hbo

I didn’t know what to call this at first. But if I had to name it, I’d say it’s the thirty-something phase. The real grown phase.

I was thinking about Rihanna—how her style evolved from her early days to now. Look at her old outfits and you’ll see a shift. She’s a mom now. A business owner. A wife. Her style matured as her life matured.

And the same is true for Issa Dee.

From Season 1 to Season 5, you can see her evolution. Not just in her confidence, her job, or her relationships—but in what she wore. The colors, the cuts, the energy. It all changed. It all grew with her.

And honestly? That’s the whole point of personal style.

Style isn’t something you can truly discover from a Pinterest board. Or TikTok. Or YouTube. Heck—not even from reading this blog. Because style isn’t a template—it’s a timeline.

Every phase of your life is your style.

Every job change, every heartbreak, every glow-up, every “I don’t know what I’m doing,” every win, every loss—it all shows up in your closet.

You can’t separate your wardrobe from your life. They’re woven together.

And I have to give a shoutout to the Insecure wardrobe team. Because whether they meant to or not, they showed us exactly how style becomes you. Over time. Over seasons. Over life.

So no, there’s not one “perfect” style that fits every age group or life stage.

Because you’re not the same woman at 25 that you are at 35.

And thank God for that.