This week, Lee Alisha of Wearing on My Mind joins to share about her experience returning to self-confidence after loss and the role of bright color in showing her transformation! We also celebrate Lee’s recent completion of an MFA, discuss why writing on Substack is a breath of fresh, and how she decides what to buy and wear.

Enjoy!

Episode Transcript

This transcript has been edited for clarity.

Welcome

You’re listening to Intuitive Style, where we believe that everyone has style. I’m Maureen McLennon Welton. In conversation with fantastic guests, we explore how to tap into our style intuition so that we can dress authentically and live fully.

Maureen: Today’s guest bounded onto my Substack feed with joy, enthusiasm, and bright color. While she might be slightly newer to our Substack feeds, she’s been making style and beauty content on Instagram for a minute, which is equally as delightful as her writing style. Lee, welcome to the show.

Lee: Thank you so much. Thank you for that introduction. It’s so sweet.

Maureen: I love seeing a new creator come on to Substack and just have such a clear perspective, POV, and you certainly accomplished that.

Lee: Thank you.

Maureen: So with that, my first introduction to you was a post about your experience wearing vibrant colors over the summer and how that improved your self-esteem. For anyone who hasn’t read that newsletter yet, what changed and encouraged you to start showing up in that way?

Lee: So I was actually maybe like a month and a half ago just looking through my camera roll and I noticed that most of my summer outfits—anytime I took a photo—it was some vibrant color or print. And I was like, I need to write about this because I didn’t realize how happy it was making me and how comfortable I felt in all those vibrant colors and everything.

A few years ago, right when COVID happened, I was a junior in college. All my classes were online. I was isolated. I was grieving the loss of a loved one. So I was not connected to myself at all—you know, a lot of people weren’t during that time.

And I started to not express myself anymore through the clothes that I was wearing. Prior to COVID and all that, I felt pretty confident in my skin and what I was wearing. My style has changed so much since then, but when COVID hit, I just started to hide myself. I hid my body. I was wearing more darker colors—nothing like the prints that I did this summer at all.

And so, yeah, when I saw all the photos of myself from this summer, I wanted to write about it because it honestly surprised me that I wasn’t realizing that that self-confidence came back. And it reminded me of when we’re kids and we don’t care what anyone thinks and we’ll just wear whatever we want to wear. So, yeah.

Maureen: Beautiful to hear that we can go through a period of kind of darkness and sadness and hiding, and sometimes we are lucky in the way that we can just find joy again without necessarily having to be super intentional about it. Sometimes it can just surprise us. And in that way, grief is non-linear and it’s surprising in all these ways.

Were you shopping differently, or was it more just like you’d had these clothes beforehand and were just choosing to wear darker colors versus now choosing to wear bright colors? How was that materially different?

Lee: That’s a good question. Some of the pieces I had, but a lot of them are new. I’ve been fortunate to work with some brands that have gifted me some items, so that has kind of propelled me out of my comfort zone—just working with different women-owned, small-owned brands.

But personally, I don’t really know what it was. I just started to embrace things that maybe would have made me uncomfortable in the past, especially because I live in Florida. We had a very hot summer, and I was like, I can’t do the oversized dark shirt and leggings every day—I need to cool off. So I started to wear a lot more linen, and some of the linen pieces that I bought had prints or patterns and colors—it wasn’t just tan or white.

So, you know, just making sure that I felt comfortable in extreme heat and also wanting to look cute in my own sense of style and everything.

Maureen: I love that too, and this is one of the reasons that I have a podcast about this. Because I think sometimes it can feel like there’s only one way to do things.

And I’m highly analytical—so when I’m shopping for my closet, nine times out of ten, it’s with extreme precision and intention and I overthink it. And I think what I’m hearing from what you’re saying is it was a little bit more organic and you were just kind of drawn toward these bright colors compared to when you were drawn toward darker colors.

Am I oversimplifying that process, or was there more analytical decision-making behind that? Which, for the record, if it is very organic, I’m jealous.

Lee: Right? Well, I’d say if I’m just shopping for everyday basics—like things that I can wear with five different outfits and remix—I may be a bit more analytical about that because I want to make sure it’ll last and I can get a lot of usage out of it.

But, you know Like in that newsletter, I had this green caftan on. When I got that, I wasn’t like, “Yeah, I’m gonna wear this every single day.” You know what I mean? I was like, I know this is probably gonna be a piece that sits in the closet, but it makes me happy and I will wear it. But it’s not gonna be like an everyday item, you know?

So I think the analytical, almost logical clothes-eye kind of goes out the window for me if it’s something I really, really like that may not be something I wear every day.

Maureen: It’s awesome to give yourself permission to do that. That’s how we interject things that we didn’t even know that we wanted. Sometimes we’re just drawn to something like a moth to a flame.

You also mentioned in the post there was a specific outfit that you wouldn’t have worn a few years ago. I think it was a little bit preppier or something like that. And I was just wondering—can you share more about maybe what changed your mind or how that change occurred, basically?

Lee: I remember the dress you were talking about. I think it was the one where I didn’t have sleeves, and it had stripes. Yeah, so that was one of those linen pieces I was telling you about. I felt really cool in it, I didn’t get hot in that dress—it was a very comfortable piece of clothing.

But a few years ago, I wouldn’t have worn it. Not because of the print or the color, but literally because of the arms—it didn’t have sleeves at all. And, you know, during COVID and isolation, I started to feel very aware of my body, but then also pick up little things that now I can look back and be like, I was being way too hard on myself.

Like, I’m blessed to have this body and to be able, you know what I mean? But back then, I was just looking at my body and picking all these little things apart. And back then, I just did not like my arms out. I needed sleeves. I just wanted to be covered, you know?

“I’m blessed to have this body” - Lee Alisha

And so that piece—I love that dress so much today. I don’t have a second thought about my arms or anything. But like I said, that didn’t happen overnight, you know? Because I felt those insecurities like four or five years ago, and now it’s 2025, and I still have my moments and stuff. It’s not perfect, you know, but I just try to show up for myself and not be hard on myself, especially when it comes to what I’m putting on my body and how I feel, you know?

Maureen: I know that you said you were grieving the loss of a loved one around that time, but it’s just crazy the way that COVID had such an impact on how we were all feeling.

I also look back at pictures from a couple of years ago, and at the time I would look at those pictures and be horrified by my appearance. And it was just—like—totally normal. My body was so normal. And I just had this horrible lens on it.

And now I look back at those pictures and I [see something really positive]. I see such a different version of myself. And for me, I would say partially that just comes with getting used to maybe looking different if your body’s changed.

But also, I think there’s really something to what you’re saying about maybe it was just the COVID of it all — and how much time we had to just sit on our phones. I don’t know. Do you feel like that’s part of it?

Lee: I mean, I kind of do, because I remember early days it was like, “Don’t go outside.” So it’s like, okay, well, I’m just going to sit inside. And sitting inside just became my normal, because like I said, all my classes were online. My classes continued to be remote until I graduated in 2022.

So I was not on campus for almost a year and a half, almost two years. I just got comfortable with the four walls of my apartment—and I was like, it’s fine, it’s great, you know? That just became normal. Then, when it was time to go outside and see your friends and loved ones, that felt strange. You kind of want to hide yourself or just stay where you feel safe, you know?

Maureen: I totally relate to that. I think that’s so fair. I mean, especially — I can’t even imagine college virtually. You sound very resilient and like you got through it and made the best of it, but I mean definitely, I think even now I’m still trying to figure out how to get myself out of the house sometimes.

Because it still feels like—I don’t know, wrong sometimes. I get what you’re saying.

Lee: Because when COVID first happened, I was like, “Oh, I am so happy to have online classes,” because I’m an introvert. I love having my own space. I was also a creative writing major, so I was like, I’m going to romanticize this. I get to sleep in, make my coffee, read my books, and do my English literature and stuff.

But then, you know, a few months of that goes by and it does a number on you.

But I see what you mean about going out now. I mean, I do think there’s a difference between, you know, really wanting to protect your peace and enjoy your own company—because I do that a lot today.

I live in Tampa, and I’ve lived here for the past six or seven years. A few years ago, I could go downtown in like 30 minutes. It’d be a 30-minute drive. But now it could be like an hour because of the drivers and the amount of people here. Sometimes I just don’t want to deal with that.

But that’s—you know—I don’t see that as me isolating myself. So I feel you on how sometimes it just feels hard to even go out now. But, you know, it could just be that you want to have your peace.

Maureen: Totally. And it’s not black or white — it’s definitely about figuring out the right balance.

Am I mistaken in congratulating you on your MFA?

Lee: Yes, yes — I graduated last month!

Maureen: Okay, oh my gosh, congratulations!

Lee: Thank you.

Maureen: How do you feel having that degree? How does that impact your outlook?

Lee: I feel really good. I can’t say enough great things about the program. I went to the University of Georgia, and it was their narrative nonfiction program. I still talk to all my classmates who I graduated with and some of my professors — it was just an amazing experience.

I’ve always wanted to write a personal essay collection, and that two-year program really gave me the skills but also the confidence to achieve that goal of mine. So I feel a lot more confident when I’m writing and doing my own thing.

But that’s part of the reason why I do love Substack and writing about style — because a lot of the things I write on the side, the stuff I want to be in a book one day, can be very emotionally heavy. So doing these shorter-form posts about color and style and whatever else — that feels good. It’s nice to have that balance.

But thank you for saying congrats. I’m still kind of in a grieving period, honestly, because I can’t believe it’s actually over.

Maureen: That’s fair — and good for you for recognizing [the grief]! Sometimes when we get to the end of a big accomplishment, we’re like, “Why am I not magically happy?” And it’s like, oh — because maybe you actually liked the experience of going through it, having your friends around, all of that.

Lee: Yeah, no, that’s so real.

Maureen: So again, congrats — and again, welcome to Substack. Especially, it’s always nice to hear that professional writers are still using the platform — I say that without a professional writing degree myself.

Lee: Girl, you don’t need a professional writing degree! I mean, I’ll be honest — when I started posting on Substack, I think it was last January. I was doing more like fashion roundups — like “this deal, that deal” — and I still like reading that kind of stuff.

But I took a break for a while this year just to finish school and everything. Coming back to the platform and finding you and other writers — I’ve just felt very inspired. Because, I mean, everything that you publish, it’s like a personal essay — it’s stunning. And I love that.

It’s nice seeing what other people have to say, and you can tell everyone’s writing with a lot of heart. That’s beautiful.

Enjoying this interview? Subscribe now to be notified when future episodes drop! Or consider upgrading your subscription to support this work.

Maureen: Yeah, I appreciate that. And same with your writing, right? I think this is a perfect segue — thank you.

What’s really nice about writing on Substack in particular is that the long-form medium — you can do this on YouTube as well — but the long-form medium allows so much more complexity in why people are choosing what they buy.

In broad strokes, how do you decide what to buy and where — and how do you decide what not to buy or where?

Lee: So when deciding what to buy, if reviews are available, I love to look at reviews. And then also, there are certain brands that I’ve really liked in the past where I’m like, okay, I have to be careful today, because I don’t know if I’ll wash this item three times and then it’s just not doing it anymore.

You know, like Gap, Banana Republic — even though I’ve been loving what both of them have been putting out lately — but I’m still like, yeah, you have that hesitance.

Plus, since I don’t have a full-time job right now, I’m even more careful about where my money’s going, because I don’t want it to either not fit and I can’t return it, or it was a bit on the pricier side and it’s just not what I thought it would be.

I try to just sit on things for a while and not do the impulse buy. Because a few years ago, I was always doing that. I’d go to Target every weekend because I love a good bargain, and I’d just look at everything. I haven’t been to Target in months now.

So I just try to be careful — and also ask myself, you know, will I be able to wear this a lot? Can I wear it with other items? Is it versatile? And if it’s not—like some of those vibrant dresses I wrote about—then I ask myself, does this really make me happy? Do I want it because I like it, or because it looked good on someone else? I try to really hone in on my motivation for liking something.

When it comes to what not to buy—honestly, if it’s out of budget, that’s usually the main thing. I’ll save a photo or a link and think, this is really pretty—maybe one day.

Also, if I’m not sure something will fit my body type—I’m very curvy on the bottom—I tend to steer away, especially if it’s just a trend on social media. If it might not work for me, that’s okay. I try not to give too much energy to trends. I just observe and appreciate from afar.

Maureen: Yeah, it’s always good to know what’s not for us.

I guess the other question, kind of off that, is—do you ever feel like there’s such a thing as enough with clothing? Do you ever reach a place where you’re satisfied with what you have? Or is that still something you’re reaching for?

I ask because I’ve gone through a lot of style transitions—mostly unintentional, as my body size and shape changed—and I still feel like I’m trying to get to some sort of “goal.” Have you ever experienced a feeling of enough or satisfaction?

Lee: Totally, yeah. I’ve felt that before, but then I’ve also had moments where I realize I need new things. Like, during COVID, my body changed—I gained some weight—so I had to buy new clothes that fit this new body. And I was fine with that. I wasn’t going to wear clothes that didn’t feel good.

But now, some of those clothes need replacing again, so it’s a cycle.

At this point, if I look in my closet, I do feel like, this is enough—I have what I need. But there are always things I want. And honestly, social media feeds into that. Let’s be real—if we didn’t have magazines, trend forecasts, or constant content showing us what’s “in,” I think our wish lists would be much shorter.

There are things I want, sure, but do I need them? No.

Maureen: Yeah. And I ask that because you sound very level-headed and grounded when you talk about shopping and buying things. I wanted to acknowledge that, because like you said, there’s so much messaging out there telling us what we have isn’t enough—it’s such a trap.

I guess I just wanted to see if I was reading you right, because you sound really at peace with what you have, and I think that’s amazing.

Lee: Thank you, that’s really sweet. Honestly, I think it’s because I was laid off last year. Since then, I’ve been jumping from freelance position to freelance position, and being on a budget has forced me to hold myself accountable for my spending habits.

When I had a full-time job, I’d justify little purchases as rewards. But now that I don’t have that steady income, I’ve had to chill out a bit.

I also started creating fashion and beauty content after I was laid off, just because I had more time. But even with that, I’ve always wanted to stay true to myself. I never want to come across like I’m shouting at people—“you need this product or your skin will never look good”—because that’s just not me.

There’s nothing wrong with creators who do that, but I never wanted to feel loud or pushy. And honestly, when you consume too much of that kind of content, you start believing you really do need all those things—which you probably don’t.

So I try to stay intentional with what I create, and I think that’s carried over into how I shop and what I buy personally.

Maureen: Yeah, and that’s so important—to know what you want to communicate as a creator. You’re doing that really effectively.

So with that said—you mentioned earlier that being on Substack has been really inspiring for you. Knowing that you’re not necessarily writing about shopping right now, what’s inspiring or exciting you to write these days?

Lee: Honestly, the free time I have now. No, but really—I was so excited to get back into Substack and just do my little blogging again. It feels therapeutic. I love putting everything together in the Substack CMS—the graphics, the layout, all of it.

And lately, it’s been amazing connecting with so many new people. A few months ago, before you and I connected, my feed didn’t look the way it does now. Now it feels like people are really supporting each other, and that’s such a nice energy.

Seeing that community makes me want to keep returning. And I think part of it, too, is trying to create a routine for myself—posting maybe once a week or every two weeks.

You know, I had a really regimented school schedule, and I was so exhausted after graduating—happy, of course, but definitely tired. I needed a few weeks just to breathe.

Doing short posts on Substack has really helped me feel like I can take steps toward my writing goals again—working on my book, writing on the side. So yeah, Substack has been really helpful.

Maureen: Super cool. So, what advice would you give to someone trying to build a wardrobe that feels intuitive and authentic to them?

Lee: I’d say just stay true to yourself. We were talking earlier about that “fake it till you make it” mindset—wearing things outside your comfort zone—and I think that can work sometimes. But for me, whenever I tried to do that, I just ended up feeling uncomfortable.

So my advice would be: start small. Don’t take it too seriously or feel like you need certain pieces to “complete” your wardrobe. Have fun with it, and forget the so-called fashion rules if you can. Whatever works for you will work for you.

For example, when mid-rise and low-rise jeans came back, I thought, that’s great—love that for y’all—but I’m not doing that. I’m a high-waisted girl; that’s what feels best on me, and that’s okay.

So yeah—just do what works for you and what makes you feel comfortable.

Maureen: Yeah, totally. Well, thank you—this was really fun. Where can listeners find you?

Lee: I’m on Instagram at @lealisha—that’s L-E-E-A-L-I-S-H-A. And my Substack is lealisha.substack.com. My newsletter is called Wearing on My Mind.

Maureen: Perfect! This was so fun—thank you.

Lee: Thank you!

Maureen: I’ll make sure all your links are in the show notes so everyone can find you.

Lee: Thank you so much.

Share this episode with someone you think would enjoy it!

Outro

Intuitive Style is produced, edited, and hosted by me, Maureen McLennon Welton. Our theme music is by Tim Reed and Jacob Welton.

In case you missed it, Intuitive Style the podcast is an offshoot of Intuitive Style, the newsletter. Head over to Substack, and search Intuitive Style to read the newsletter—which covers reflections on personal style, guest features, and encouragement that there is no wrong way to get dressed.

If you enjoyed this episode, please rate and review on Apple Podcasts or Spotify, or share with someone who might enjoy it.

Don’t forget to subscribe as new episodes drop weekly on Fridays.

Thanks, see you next week.

Get full access to Intuitive Style at maureenwelton.substack.com/subscribe