How Alexa Webb Trailblazed a Path for Plus-Size Fashion

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I had the opportunity to sit down with Alexa Webb and discuss her story of building a fashion empire after she saw a lack of inclusion in the industry for plus-size individuals. Alexa is a sharp, articulate, and kind-hearted individual who bravely followed her passion and allowed it to take her into new and exciting terrain. 

From her family of entrepreneurs to a lifelong passion and interest in fashion, her life seemed to align and lead her to leaping and becoming a full-time plus-size fashion blogger.

Even more impressively, Alexa is now using her platform to advocate against the discrimination plus-size individuals experience every day, especially regarding healthcare inequality. 

Alexa’s story will motivate and inspire you to follow your passions and give you some takeaways for your potential side hustles or business from a trusted pro in the industry.

Listen to Alexa’s interview on the go with our Marketing Unleashed podcast!

Plus-Size Discrimination Happens Every Day

Question: Can you speak on the plus-size discrimination individuals experience and why you feel called to advocate for equal representation in fashion and clothing?

Alexa: There’s a lot of discrimination, and I think many people aren’t necessarily aware of that. When you look at statistics – there is a lot of actual discrimination that they face in terms of equal rights and just to be treated with respect. 

My most recent cause is discrimination in the medical field. That’s something I have experienced firsthand. I shared some things with my followers and was shocked at the number of people saying, “Oh my gosh, I’ve had either the same experience or something very similar!” Or telling me these horrible stories that they went to the doctor, complained about symptoms, were told to lose weight and that’ll take care of it. No tests, no nothing. And then later, they found out they had a tumor or a significant thing that was completely overlooked because of their size. 

Plus-size individuals aren’t even getting basic screenings for health problems. And that’s just terrible. So yeah, it impacts us in very real ways.

Obviously, I have a fashion blog, so that’s not as serious, but I also think being able to dress well and feel like you are dressing well makes a huge difference in how you feel about yourself and how you present yourself to the world. I think people experience negative interactions when they don’t feel confident in their skin. And I think to style your clothing and wear stylish clothing period is really helpful to boost your confidence. Then you step out into the world feeling comfortable with yourself, and then when you interact with other people, they sense that as well. 

It doesn’t feel good when you can’t find anything that fits you correctly or that’s stylish in your size. So I think it’s really important to take the time to style your clothing and try to find what works for you. And sadly, as plus-size individuals, it’s always going to be more challenging. At least that’s been my experience my whole life so far. 

It’s getting easier, I will say, but it was really about trying to figure it out with what was available in the market for a very long time. And how to make it look more stylish than it was because so many frumpy, terrible, crappy garments are being designed for plus-size women. There were blogs, thankfully, but there weren’t a lot. And there wasn’t a lot of representation on social media at the time. I came to that, and I just wanted to show people that it is possible. It’s a little messed up; we have to go through the extra effort to dress or be fashion-forward, but it is possible, and that’s why I started doing what I was doing to show people it was possible. And that was my goal. 

The Beginning of Alexa’s Blog

Question: What cross roads lead to you taking matters into your own hands by beginning to post plus-size fashion inspiration? 

Alexa: I didn’t see a lot of representation. I discovered Polyvore randomly. I don’t even remember how. I was trying to make some collage or something. It was nothing to do with anything I do now. I found Polyvore and I thought it was cool because it was. I should say – Polyvore no longer exists. But these people were making gorgeous collages, and some of them were very fashion-focused, and they were just fascinating to me. Like pieces of artwork almost. And I was like, wow, this is amazing. 

And so, of course, I started looking through and searching for plus-size, and there was nothing there. At that time Pinterest was first getting started. And when I got to Pinterest, oh my gosh. That was amazing. I had never seen anything quite like it before. I’m a very visual person. So for me, it was just so my platform. I was inspired by it. And then, of course, I started looking for plus-size fashion. And at that time, there was just nothing. 

I thought it was so sad because I had found this platform, and it was a great resource with all of these inspiring images and amazing fashion things and, I was like, where are my people? Where are my sizes? I’m looking at beautiful outfits and thinking, well, none of this will be available to me. And I knew this was a problem. 

At the time, I was following many different blogs, and I started Pinning everything I was coming across in my search and then Pinning the things that I created on Polyvore. Then I started to have this audience, and it was just completely unexpected. Of course, I hoped that other people would see what I was Pinning, but I didn’t expect it to happen, you know?

Alexa Webb interview screenshot of her website
Alexa’ Website

Alexa’s Career Background

Question: Do you have a background in business, fashion, or anything related? 

Alexa: No, I don’t. I mean, I do, but not a formal education. I have a degree in Psychology, which has absolutely nothing to do with either of those things. But my grandparents had a business, and my parents had a business. I’m actually a fourth-generation business owner. There’s this kind of no escaping it. I grew up in those businesses, working in them and I naturally absorbed some things. 

And also, my mother is really into fashion. That’s always been her thing, and she’s very passionate about it. I grew up in a house where there was Vogue and other fashion magazines around. I was always flipping through those. My parents owned a fabric store, and there was a lot of fashion when they were making clothing. Just being exposed to all of that, I think, gave me the interest and passion that I have.

And then, being that I have been larger, my whole life, even, as a kid or a teenager, trying to find things to wear that were stylish or on-trend, or even expressing myself, was so challenging. Especially back then. It’s a little easier now, but I think that drove me to figure things out. I didn’t find it acceptable that there wasn’t much being marketed to me. Even just in my age group, there wasn’t plus-size clothing available. I would basically look at clothing designed for frumpy older women and then try to make it into something interesting. And so I think in a sad sort of way, that led me to learn how to put things together and see things differently.

Lauren: It’s in your blood with your parents’ business, the fashion industry, fabrics, and all the entrepreneurial energy in your family. It’s kind of like you were destined to do this.  

Alexa: I KNOW, and it’s so funny because I just never really put it together. People would ask me things like this, and I’d go, “I don’t know. I have a degree in Psychology, and I used to do clinical research for a living. I don’t know how I ended up here.” But then when I really started to think about it, I was like, whoa, it kind of does make sense. Just not what I expected, you know? Not at all what I expected. 

Deciding to Become a Full-Time Blogger

Question: Was there a moment when you knew it was time to pivot from side hustle to a full-time career? 

Alexa: I was going to say I was really lucky in some ways, but that’s a weird way of looking at it. But it’s true. I was working full-time while creating my little sets on the weekends when I had free time. Working a very busy full-time job that was sometimes very stressful. I didn’t have a lot of time. 

But I ended up having an injury, and I had to leave my job, which was devastating to me at the time. I didn’t know what I was going to do. Or how I would make a living. It was horrible. It was devastating. But I consider myself lucky in a sense because it pushed me to throw all my energy into my blog.

I’d been talking about starting a blog for a long time because, at the time, I already had like 70,000 followers, maybe more. And they had asked me, do you have a blog? Where’s your blog? And I’m like, I don’t have one of those. So I had been talking about doing it for a while. In fact, I had even posted years before, “If I get 20,000 followers, I’ll start a blog.” Well, I never actually did. So that’s the funny part, but I had even bought a domain, I just never pulled the trigger.

So when this happened, I decided to throw all my time into it. Just for my sanity, because I didn’t know what to do with myself. At the time, I had already started monetizing a bit on social media. So I was a little bit more familiar with affiliate marketing and things like that. 

Then I started monetizing my blog, and I was shocked. I was shocked because I was getting all these clicks. I was getting so much traffic right off the bat. And in turn, of course, I was making money, and I was like, wow, maybe this is a thing that I can do.

So I look back at that moment as horrible in so many ways, but I was so lucky because I don’t think I would have been pushed into that position. Or it would have taken longer but, it was just almost like the universe pushing me into something, you know? It was a weird turn of events, but it was a good thing.

Alexa Webb interview screenshot of her Pinterest
Alexa’s Current Pinterest Account where she received over 10 MILLION views!

The Best Advice Alexa Has Received and Advice She’d Give 

Question: What was some of the best advice you received regarding growing your business and following? And what advice would you give to someone starting their own business or blog right now?

Alexa: It’s so important to be passionate about it. I always say choose something that you will never, ever, ever, ever, ever be sick of. You need to be able to talk about it, research it, learn about it, and write about it. It has to be something you’re so passionate about, and that never gets old. You have to have that drive and that passion because, without it, you get burnt out. Even I get burnt out sometimes, it happens. But then new fall collections come out, and I’ll be like, oh, I’m excited. It’s just constantly about being inspired. 

The other thing is, I don’t think people will be very successful if they’re in this for the money. There are a lot of different, much easier and better ways to make money. This is hard. There’s going to be a struggle and success doesn’t happen overnight. It took me years to build up the following that I have. And I had no expectations. If I had any expectation for making money early on, it would have been very different. I probably would have been making very different content. And I don’t think things would have happened the way they did. 

Over the years, I have listened to and seen many interviews with other influencers and bloggers. And they kind of all say the same thing I’ve noticed. Saying they didn’t get in it to be famous or to make money. It was because they were passionate about sharing something. 

So, I think. Yeah, it’s important that you’re really passionate, and that’s what you’re in it for. And I think if you do that, the money doesn’t matter. And then, ironically, that’s when the money does come to you. There are times when I put out content, and it doesn’t do well. Sometimes I know it’s not going to do well, but I do it anyway because it’s my content, and I love it. I know it’s gonna kill the algorithm, but I don’t care, you know? I feel a certain way about things, and I want to share things. So I think that’s my number one piece of advice. If you’re looking to make some money quickly, that’s not going to be enough.  

What Outside Factors Helped Alexa Take Her Business to the Next Level

Question: What outside factors and support helped you take your business to the next level?

Alexa: One of the things I didn’t do initially was I didn’t join the plus-size blogger community. I don’t want to say I felt like an outsider because that’s not really true. I just didn’t really know them and it was a very, very isolating experience. I went from having coworkers and working in busy environments. And now I’m in my house by myself on my laptop. 

I started making an effort to reach out, not just to people, but to also join groups and different blogging groups. And now I actually have a couple of communities I belong to that are really, really helpful. Not just as far as, let’s give each other tips on how to increase our traffic or whatever, but an actual like, “Hey, yeah, this is lonely. This is hard at times. Are you having trouble with this?” It has been really helpful to have that support, and I wish I had sought that out a little bit earlier. I would also recommend finding a group, a community, people that you can bond with and relate to because it’s really important.

I also have to give credit to my mom. She is very supportive, and I’m always sending her stuff asking what she thinks, and she’s always giving me feedback. I don’t have an office with coworkers across the way that I can be like, “Hey, check this out. What do you think?” It’s just me. And honestly, after hours of looking at stuff, I have no idea. I don’t even know anymore. I’m just in my head, and it’s not a good thing, so it’s helpful to have my mom there. 

Alexa on the Pressure of Being an Influencer

Question: Is it hard putting yourself and your vulnerability out there and subjecting yourself to criticism? 

Alexa: Yes, and it gets harder. I didn’t realize that it gets harder as you get more popular, but it does. Suddenly it goes from I’m sharing this cute thing with a few people to eventually thousands of people. And some people are sending me messages saying they’re disappointed or upset or don’t like this.

I don’t share as much of my personal life. Part of that is, I’m a private person. The other piece is that I want to protect myself. I do share, but it’s a fine line for me. It’s a balance, a constant balance. I do try to share some things and open up a bit, but even that can be hard. So yeah. It gets harder. 

And the algorithms are brutal. Sometimes I’ll be putting things out there. And even though my core audience is still with me, on Instagram, for example, something will just tank, and I’ll be like, “Okay. People don’t like this. It’s not good.” But honestly, I don’t even know if that’s true because I look at how many people are still visiting the website, and they’re still clicking. So it’s hard to gauge, you know? 

Alexa Webb interview screenshot of her Instagram account
Alexa’s Instagram Account

Alexa’s Ode to Tailwind

Question: What has saving time with Tailwind allowed you to do in your business that you would otherwise not have had the time to do? 

Alexa: Tailwind changed my life. I know that sounds so profound. But I truly mean that because back when I had a full-time job and was doing this as a passion project, Tailwind helped it become a side hustle where I could monetize and make some income.   

I didn’t have time to do anything. I mean, I was working like Monday through Friday. I was putting in time on the weekends, but that doesn’t really work in the long run. You can’t disappear from social media five days a week and then expect things to go somewhere. So, getting Tailwind for me was huge because it would be Pinning while I was at work and helped bring in an income while I was doing another job. 

It also proved to me in a sense that this was something I could make money doing. And I don’t think that would have been possible. or at least not to the extent of success that I’ve had, without Tailwind. 

Tailwind has also made my life a lot easier. Pinterest has changed dramatically – especially recently. But for a long time, it was all about pinning your content plus other people’s content.  It was all about having a variety of sources and a variety of things. And Pinterest wanted you to switch it all up. 

So for me, Tailwind was crucial because of the limited time that I would have to find things to Pin. It allowed me to do it in such a way that it was automatically shuffled up. Tailwind allowed me to be methodical about finding sources and then sharing them in a more pleasing way to the audience and, of course, the algorithm. I wouldn’t have been able to do that otherwise. My account would have sucked because it would have been the same thing all in a row. It was really important at the time, and it’s still really important. But for growing back then, it was crucial.

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Alexa’s Favorite Tailwind Feature

Question: Which Tailwind feature or perk of the app is your favorite?

Alexa: First of all, I think that the analytics are great. That’s been really quite helpful. And the Pin Inspector is fantastic. Not only is it telling you what’s doing well and what’s performing well, but then it allows you to – right there – repin it and to repin it wherever you want it to go. And that’s just so helpful. 

Even today, the analytics on Pinterest are just not that helpful. Even if you find something that is performing well, and you’re like, I want to repeat that, and it’s not that simple. So it’s amazing that with Tailwind, it’s just like click, click, done. It’s one of my favorite things, honestly.

What’s Next for Alexa Webb?

Question: Last but not least, what’s next for you and your business?

Alexa: I have lots of ideas. It’s more like if only I had more of me to go around, and that’s always the challenge, right? I want to work on having a newsletter and having closer conversations with my audience. I think email is a free way to do that. An email newsletter is something that you own, and I think that’s so important. 

Then, of course, we have a real push toward video with social media, and I’m creating static images and collages. So my challenge now is to figure out how to make it a bit more interactive and engaging, and video seems to be the way to do that.  

I started working on some things and I’m learning new skills constantly. Like, I don’t know anything about video. I did one makeup tutorial, and the editing was probably horrific. I posted it, and I was like, do I really want to put this in the world? It’s so bad. But that is one of my other pieces of advice is that sometimes you just have to do it even though it’s going to be bad. 

If you look at what I posted at the beginning of working on Polyvore. Oh my gosh. Sometimes I will go back and look at my work from like ten plus years ago. And oh, wow. It’s bad. I mean it’s really bad. 

So the point is, had I not pushed myself to go ahead and get it out there, I wouldn’t have gotten to where I am. So you have to let it go and just be like, yeah, it sucks. It’s not good. And that’s kind of where I think I’m headed with video. So it might be a little rocky for a bit!

Alexa Webb interview old Poyvore design

One of Alexa’s first designs on Polyvore from over a decade ago verses a recent outfit she designed.

Alexa Webb interview recent outfit she designed

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Where You Can Find Alexa Webb

Alexa is a prime example of how someone can begin monetizing and growing an audience even with a full-time job. And her advice of creating from passion, choosing something you’ll never get sick of, and being driven based on interest/passion and not money is some of the best advice, if not the best. 

I have no doubt she’ll keep excelling as she evolves and develops new skill sets to help her reach new goals, including venturing into video and email marketing. 

If you’d like to follow Alexa, which I highly recommend you do, you can go to her plus-size fashion blog. Her Pinterest account, which has over 241K followers. Her growing, evolving, and tastefully styled Instagram account. Or her fun and interactive Facebook account.   

Watch the Interview:

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Alexa Webb sat down with us and talked about how her blog was created, how it became so successful, and what advice she'd give to someone just starting out.

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