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My Posing Workshop and Photoshoot with Tess Holliday: What I Wore and the Confidence Boost it Gave Me!

Andrea by Andrea
12 months ago
- Last edited by: Marie Denee -
Reading Time: 11 mins read
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My Posing Workshop and Photoshoot with Tess Holliday: What I Wore and the Confidence Boost it Gave Me!
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When I heard that the Iconic Tess Holliday was hosting a posing workshop and photo shoot I knew I had to do it. It was just the right time for me, since I was almost finished with my book and I knew I needed to refresh my branding photos. 

I am a firm believer of the power of posing and fashion to pull us out of our slump and into a more confident version of ourselves. 

Come along with me as I touch on the inspiration, outfits, and the final looks from my confidence inspiring photo shoot with supermodel Tess Holliday. 

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Preparation (aka Shopping)

For the shoot we needed to select 2 outfits. As a former celebrity, boutique, and wedding stylist, I knew that I needed to find outfits that felt like me, and to have a range of looks to change up pictures just in case I ended up not liking one after. 

I knew I wanted to go for more of a dramatic or editorial look and wanted the first look to be ethereal and flowy, and the second to be more form fitting. As far as hair and makeup, I wasn’t sure until after I got my outfits on lock. 

The day before the shoot I made the long drive from Phoenix to Los Angeles to stay at the lovely Hotel Proper. I brought some back up options with me, but knew I was in good hands. I scheduled a styling session at the Plus Bus, and also had my eye on a few things from Proud Mary which was conveniently located en route to my appointment. 

Here I was, less than 48 hours until my shoot and not a single detail of my outfit had been locked down. Spoiler alert: it all works out. 

First Stop to Prepare for my Tess Holliday Posing Class? Proud Mary Fashion

What I Wore to My Confidence Boosting Photoshoot with Tess Holliday- Proud Mary Fashion

I had been  shopping their online sales for years, but it was my first time coming into this hidden gem and walking in felt like a warm hug from a very 90’s living room. Soft girls are not only welcome, but we’re front and center. 

I immediately felt like a main character. 

From the meticulously curated vintage, to the handmade accessories, to the home decor finds – I was in heaven. And there it was. 

What I Wore to My Confidence Boosting Photoshoot with Tess Holliday-

Pink…. giant buttons… stripes… I knew it had to be included in my shoot. This piece was part of the Proud Mary house label designed by founder Jessica and it was perfect. I snagged several other pieces for my closet, gave Jessica a big hug, and headed down the street to my next stop.

Next Stop: The Plus Bus

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When I arrived at the beautiful Plus Bus Boutique’s Highland Park showroom I was welcomed in and introduced to my stylist. I had sent them a little information in preparation for my shoot and Cassia led me to the fitting room where she had pulled items she thought would fit my theme. I’ll just say this: She understood the assignment. 

Now as a former stylist, with clients such as Brooke Hogan, Kate Hudson, and the late Dr. Donda West I knew how to make a person feel seen… but this was the first time in my entire life that I had allowed myself to be styled. This was the first time in my life that I was shopping IRL with so many luxury options that just fit and felt like it was made for me. 

What I Wore to My Confidence Boosting Photoshoot with Tess Holliday-

One of the first dresses Cassia had picked for me was this deep pink slip dress by Baacal. I put it on and was brought to tears. It just felt so me. It would also pair perfectly with my Proud Mary button shirtdress and I had at least one outfit locked down. 

After a few more outfits, and again adding some for my closet for later, we were accessorized and ready to go. 

As we scoured for a second more ethereal piece I asked if maybe they had something with Selkie vibes that could work. Just then Jen Wilder brought over one that had just come in on trade and hadn’t been processed yet. It was perfect. 

My Inspiration Mood Board:

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Back at the hotel I was laying out and finalizing earrings and shoes for my looks and checking social media for some inspiration. Tess had messaged me the links to the hair and makeup artists for me to peruse and I came up with a few inspiration shots for the shoot. Here’s the Pinterest board I created!

Look One: Vintage Fever Dream

The Inspiration

I was inspired by Natalie’s pose and the angsty feelings from Kimberley Gordon’s posts. There was real main character energy which was exactly what I was going for. 

What I Wore to My Confidence Boosting Photoshoot with Tess Holliday- The Inspiration
via @nataldee on Instagram
What I Wore to My Confidence Boosting Photoshoot with Tess Holliday- The Inspiration
via @wedreamoficecream on Instagram

The Shot:

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Look Two: It’s a Movement and a Moment

The Inspiration:

This look was inspired by Barbie and just pink on pink on lavender on pink. When creating this outfit I focused on classic Barbie Maximalism aka Barbiecore. Mixing textures was the best part of this, the deadstock silk of the dress, the light airy button up, and velvet wrapped hoops all told a story. 

The Shot: 

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Look Three: Quiet, Curvy, Confident

The Inspiration:

This look is more toned down, like peeling layers back, and it just feels calm, serene, and sexy. I was inspired by this gorgeous photo I found through the makeup artist of Bree Kish who just slays in a different shade of the same Baacal slipdress. 

What I Wore to My Confidence Boosting Photoshoot with Tess Holliday-the inspiration
via @breekish on Instagram

The Shot:

What I Wore to My Confidence Boosting Photoshoot with Tess Holliday-

Confidence Boost here we come:

With the workshop and expert team, I was pretty sure I’d get at least one photo that I liked and I thought that’s what would build my confidence… the final result. Truth be told I felt a boost to my confidence from the second I finally clicked “Book” on the shoot when I saw the limited slots disappearing. I think part of it was that I started seeing myself of worthy of the experience. I’m not a model, but I could do this. For fun, for learning, I was investing in myself.

I felt more confident through each step of the process. Every part of the planning, the playlist I chose for my drive out to Los Angeles. Working on my Pinterest mood board. The body positive shopping experience I had at Proud Mary and the Plus Bus. I had been slowly building up my confidence throughout the process. And the photo shoot experience was a culmination of everything up to that point and I could not imagine a better shoot.

Not only was I pampered from start to finish by Tess and her team, I got to meet other like minded women in a truly uplifting environment. We laughed and shared stories. We sang along to the music. I learned new poses that helped me up my selfie game.

Andrea and Tess

If you have been hiding in the back during family photos or opting out of being photographed, do yourself a favor and plan a photo shoot with just you. I used to try to hide in photos too (and yes, sometimes I still find myself hiding.) Whether you do a packaged photo shoot like I did, or set up your photo timer and do a DIY shoot, there’s nothing like a great photo of you, as you are today, to boost your confidence.

I challenge you to try some of the poses from my shoot to see if any work for you. If you aren’t quite there yet, there’s a great community here at TCF to showcase all kinds of bodies and inspiration. Maybe just start building a mood board with inspiration for one day, just in case.

I hope this feature provides some inspiration for your next DIY or professional shoot. The team that Tess put together for this event was extraordinary. Thank you Amber, Autumn, Jessica, Cassia, Jen, and Julianny for bringing my vision to life!

A special thanks to Tess Holliday for creating this opportunity for me to get in front of the camera. Your posing expertise (and fortitude with a leaf blower) helped me get the best shots and I am forever grateful for your contributions to the plus size community. 

Shoot Credits:

Posing: Tess Holliday

Hair: Amber Rose 

Makeup: Beauty by Autumn

Stylist: Cassia at Plus Bus

Photographer: Julianny Casado 

Outfit 1:

Dress:  Selkie 

Shoes: Camper Koborah  

Earrings: Pink Bows from Plus Bus

Outfits 2 + 3: 

Slip Dress: BAACAL  

Striped Button Down Dress: Proud Mary 

Shoes: Vintage from Plus Bus 

Earrings: Velvet hoops from Plus Bus

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Tags: body confidenceplus size photoshootself confidenceTess Holliday
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Andrea

Andrea

Andrea is a queer artist and fat positive coach living in the Midwest. When she isn't writing about her lived experience overcoming barriers as a fat creative, she helps brick and mortar boutiques create spaces where curvy fashionistas like you feel like the main character.

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