Fashion, Featured, Thoughts

Photoshoot with Charles Torrealba & Miss Rockabilly Ruby

Back at the end of September, I jumped in my car and headed for Chicago with a suitcase full of clothes, a garment bag stuffed to the bursting point, and a heart full of dreams: I was on my way to my very first professional photoshoot. No one’s ever accused me of doing things halfway, so I decided to jump right in with the amazing Charles Torrealba and Miss Rockabilly Ruby! I was dying to share about my experience, but it’s hard to write a post about a photoshoot experience without the photos. Now that I have my final, edited images, I’m so, so excited to share them (and the story) with all of you.

I’d been itching to do a photoshoot for a long time, but kept waffling about actually committing to it. I was worried it was vain or a waste of money. When Miss Ruby announced she’d be bringing her Beauty School workshop to Chicago and that she’d also be offering photoshoots, it was the push I needed to pull the trigger. (Read all about my time at Miss Ruby’s Beauty School!) Not only would I get a chance to shoot with an amazing photographer, but I’d get to have my hair and makeup done by someone I’d watched on Youtube and across social media for years. Who could say no?

The shoot actually took place in a Chicago Airbnb, which was super nice. I feel like an official studio space could have been really intimidating for my first time, so it was nice to have things feel a bit more homey and casual. Everyone working on the shoot was so sweet and friendly! There were plenty of great tunes and laughs while I was getting styled, including the Most Amazing Prince video. (And I even got to see the tail end of the lovely Holly Rose doing her shoot!) My only experience having my makeup professionally done before this was as a bridesmaid…that makeup artist definitely wasn’t as aligned with my aesthetic, I’ll say, so it was amazing to have a fabulous pinup look done. Paired with the hair, I seriously couldn’t stop looking at myself…I felt like a doll! (Also just so you know, Ruby said I had perfect doll lips, so I’m just going to go ahead and have that put on my tombstone.)

I got to shoot three outfits with my package, and I brought about a zillion different looks with me. I’m glad I did, because it was really helpful to have Charles go through and pick out which pieces would photograph best. We started with this ultra-moody lighting and some separates that I honestly threw in the bag last minute in case I needed back-up.

Top: Modcloth | Skirt: Steady Clothing | Shoes: DSW | Gloves: vintage | Fascinator: Ebay | Earrings: Pinup in a Pack

I’m so in love with how dramatic these photos turned out. I did let Charles know when we got started that I’d only ever shot with photographers who were friends, and that I was totally open to & would appreciate direction. He was so helpful with posing recommendations (especially when he demonstrated pinup girl poses for me…) and helping me figure out the rhythm of the shoot. I was especially excited to wear true vintage gloves that my grandma gave me with this outfit.

I’m ready to saunter into some unsuspecting private dick’s office with long legs and an even longer list of problems, and a backstory that’s as dark and sharp as my eyeliner.

My lovely friend Kaitlin says that this photo means I need to write a mystery novel so that this can be the author photo in the book jacket. Do you agree? Behind the scenes exclusive: I was too tall to rest my elbows on that bookcase, so I’m definitely squatting super awkwardly just out of frame. I’m glad I was able to pull off a cool, aloof and not “oh my god my thighs hurt” look in at least a shot or two!

Next up we took things…to the bedroom!

Dress: Pinup Girl Clothing (discontinued) | Earrings: Pinup in a Pack

The main thing I learned during this segment of the shoot is that it is really, really hard to look cute and pose while sitting on something soft. I look kind of like I’m casually sitting on this bed, right? WRONG! I am arching my back and sitting up as straight as I possibly can, to the point that I felt it in my abs the next day…which is partially because I am just generally squishy and weak, but seriously. Advice from Charles to live by: “If it feels bad, it probably looks good.”

Some day, my prince will come… I really loved these shots too. I had such a hard time picking my final selects to have edited. The subtle hint of a reflection in the window, the softness of the curtain agains my hand…it’s all too much!

The bedroom had these fabulous glass French doors that were just made for dramatic posing. Fun fact: I was trying very hard to look lovely and dramatic while there was a lamp like a foot away from my face and another Milwaukee pinup, Pamela Marie, getting her hair done right there. I think it turned out okay anyway!

Dress: Pinup Girl Clothing | Wrap: hella old idk | Necklace: Modcloth forever ago

For my final outfit, I’d intended to do something spooky, but it ended up being super classy intead. This is actually the wrap that I wore to my prom, which I semi-recently rediscovered and wore to present at an awards show, and lo! Here it is again, eternally captured in beautiful photos. And I actually just now while writing this post noticed that you can see my bag in the corner of the shot, but I’m honestly into it. It coordinates pretty well with the look!

I very rarely have photos with my glasses off because, well, I need them to see, and I usually feel like I look super weird without my glasses on. I’ve generally been convinced that I need glasses in order to provide some definition to my face, since it’s otherwise pretty uniformly soft and sloping and pale all over, but damnit, these photos are really beautiful. Shows what I know!

All told, the whole shoot, including hair and makeup, took about three hours. It definitely was different to shoot with a pro photographer than to snap my own pics in my living room, but I will say that I think my OOTD experience was invaluable. I’ve already gotten so much more comfortable with posing, and I felt a lot more comfortable with it than I would have going in cold. (Check out my post on posing tips!) That said, I think I picked up a lot of great tips during that quick shoot too, and I find myself mentally directing myself with some of Charles’ advice when I do my outfit pics. (Mostly “soften your hands!” and “soften your eyes!” – I definitely have a tendency to go bug-eyed in photos. I have an intense resting gaze!)

If you keep up with my Instagram story, you might know I have another shoot booked at the start of the year (ahhh!), and I 1000% recommend taking the leap and going for it if you think that it’s something you might like to do. I’m really proud of these photos, and I had so much fun taking them. It was an experience that I’ll totally treasure. Thanks again to Charles & Ruby for making my first shoot a success!

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