Interview with the Tomboy Toes Photoshoot Creative Team

On the heels of the very first photoshoot for Tomboy Toes, we wanted to sit down and chat with the talent behind the shoot and learn a little more about their experience working with the product and for the company.

Alex Perry and her wife Steph Ash-Perry modeling for Tomboy Toes - photo by Gryfeathr photography.We took the time to conduct an informal little Q&A with the lovely folks Lindsey, Steph, and Alex. Lindsey is the owner and talented photographer behind Gryfeathr Photography, and Alex Perry was the main model appearing in the different photos. Steph was the brains behind the outfit selection, the makeup, and the locations - as well as being Alex’s wife in real life, and the model who joined Alex for the wedding-themed shots.


Tomboy Toes: First off, thank you so much for all of your combined effort. You really blew us away with the photos that came out of this two-day shoot. Can you tell us a bit about what it was like working together on this shoot?

Lindsey: Thank you so much for asking me to work with you all on this project! Working with Alex and Steph was fantastic, as always. I’ve done personal creative shoots with them before, so we already had a good sense of how well we work together. Once we started to tackle the work it was smooth sailing. Having people on hand to handle some of the logistics, like styling and site scouting, made my job trying to capture the best out of both the product and our models a lot easier! I couldn’t have asked for a better pair of folks with which to tackle the work! Despite a rainy day, they really rose to the challenge.

Alex: No, thank you for this chance to do this! It was definitely a really fun and positive experience for me-- and without Steph and Lindsey, I don’t think it would have turned out nearly as well, at least not on my end. I love working with Lindsey. When we were thinking of photographers we’d want to shoot with, she was our first choice, and I was so glad when she accepted-- and so were my nerves! Working with someone new, or someone who didn’t know me would have made it so much more difficult. And then having Steph there… It was just a dream team. She made me look so good, and feel so confident, and Linds was there to capture that! Steph knew how to get the looks she was envisioning as the stylist, by telling me specific situations to think about while we were shooting. I love both of them so dearly, and though I was honestly scared I wouldn’t do Tomboy Toes justice, they made it work so well.

Steph: Really though, thank you for the chance to work on such a project! It really was an experience - an exceptionally positive one, at that. It was incredible to work with Lindsey and with Alex, considering we’ve collaborated on some personal work before, and it’s always a joy! A cold joy, but we had fun, haha. Lindsey is a great listener and an incredibly talented photographer, and Alex’s first steps into modeling were so good - she’s always been a little theatrical, and it really worked for this. They both really shone in the final product. It was an incredibly smooth process and overall deeply enjoyable, especially since all of us believe so heavily in Tomboy Toes as a brand!

Alex Perry models the Roguish Brogues in black - photography by Gryfeathr photography. Tomboy Toes: That’s awesome. The three of you really came together as a fabulous team and Tomboy Toes is extremely appreciative of the work you put into this photoshoot. Lindsey, much of your work in the past has been as a professional cosplay photographer. What sort of differences have you found in your work with Gryfeathr Photography when it comes to commercial fashion photoshoots as opposed to cosplay photoshoots?

Lindsey: Cosplay Photography is a fairly informal field, born out of trying to capture the brilliant costume-work of fans bringing to life designs that sometimes appear impossible. There’s a really great energy in that community dedicated to craftsmanship, and a creative outlet for trying to say something about an existing story. When it comes to commercial work, you have to bring the same passion to bringing out the best in the product, and lifestyle shots are some of the best ways to do that. Trying to communicate a feeling, a story, that connects the customer to the product isn’t too far different from my cosplay work. But in many ways, it’s sort of a relief! Cosplay photographs are often taken in restrictive environments, but for Tomboy Toes we could choose exactly the right location and I could call in some backup so I can remain focused on the photography work, rather than wrestling the environment.

Tomboy Toes: Well, you certainly did a fantastic job with capturing the feeling and story behind Tomboy Toes with the work you did on this photoshoot.

Steph, as the primary coordinator when it came to picking the outfits, what process were you going through when it came to matching the different shoe styles and colours to an appropriate combination of clothing? Do you have any tips you could suggest for people who are just getting into formal masculine shoes and are unsure of how to pair it with items from their wardrobe?

Alex Perry models the Downtown Dappers in black - photography by Gryfeathr photography. Steph: Thank you for the compliments, aha! As someone who worked formerly in high-end retail merchandising I had a fair bit of experience to pull from, especially because I spent a lot of my time working on menswear, and Alex tends to lean a little more in that direction when it comes from personal style. The goal was to keep the outfits neutral enough that the shoe would shine through, but styled enough that it turned into more of an editorial shot than an advertisement.

I wanted to pick things that looked lived in, that Alex had just pulled out of her closet and put on. Tomboy Toes is great because people can really live their lives in shoes like these - whether they’re wearing them to the grocery store or to their wedding and everything inbetween.

As far as tips for getting into wearing more formal clothing, you’ve gotta trust your comfort level. A good way to start is a nice pair of jeans with a really great shoe - having nice accessories that are similar in tone or colour drives your outfit up a notch and really makes it shine. What you wear is less important than the fit! If your clothes fit properly you immediately look more polished. Experimenting is key!

Tomboy Toes: Great tips. It can be really hard for someone who wants to move towards a style but only has the budget (or the courage!) to do it one piece at a time. Key takeaways: focus on fit and start with accessories. Thanks!

Now, on to Alex. You were the primary model for this photoshoot. First of all, you looked fantastic. Which of the looks did you have the most fun shooting?

Alex Perry models the Roguish Brogues in light brown - photography by Gryfeathr photography. Alex: You’re going to make me blush again, I swear. Past that, the most fun shoot by far was for the brown Roguish Brogues. We called it the ‘Dad Look.’ I felt the most in my element, and it was just fun. There were times I just walked off to do something while Steph and Lindsey talked about what kind of shot to do next, and then someone in the group would yell at me to ‘Stop! That’s perfect!’ So I did, and with a few tweaks we’d have another shot. We did so many different shots, and there was so much to do in the park we shot at.

Tomboy Toes: For the readers, that’s the shoot that was done with the green umbrella. The fun you were having definitely shines through in those photos, so it’s delightful to hear the emotion there is genuine.

You did a wide variety of shots, with everything from romantic to whimsical to powerfully charismatic. What kind of preparation did you do to get into the right frame of mind for all these different outfits and different tones?

Alex: I’d like to say that I’m some kind of fantastic actor, and did it all on my lonesome, but that’d be a lie. Steph was the mastermind, again, here. She knew exactly what she wanted from me, and how to get it. She’d tell me how to think, what kind of scenario to put my head in, before we started. Considering she knows me better than anyone… I don’t think I would have been able to put as much character into each shot without her!

Tomboy Toes: I guess that’s one of the many benefits of having your wife on set for a photoshoot! Now a question for each of you - what would you say was the most difficult or tricky part of the photoshoot for you?

Lindsey: The weather! We had a lot of rain recently, and it wasn’t something we could afford to schedule around. Luckily, the rain liked to hold off in the morning, and the result of a fresh rain is a beautifully saturated look to a lot of background elements. We decided to give a nod to the rain with some of the lifestyle shots, taking advantage of what could have been a difficult situation to capture some nice, dynamic looks.

Steph: The weather was a challenge, certainly, but I think it was getting Alex a little out of her shell. I could feel the nerves rolling off of her all morning of the first day while I was doing her makeup and getting her styled! She was really nervous about the shoots but with the right encouragement she definitely delivered.

I also had something of a time matching the brown Brogues. I was terrified of them! They’re beautiful but a very warm shade of brown and it’s hard to match in a styling sense, but then Lindsey had this perfect little green umbrella and it all just clicked. I’m really satisfied with those shots, haha.

Alex Perry models the Downtown Dappers in blue - photography by Gryfeathr photography. Alex: The most difficult part for me would have to be a tie between the cold and my own fears of looking dumb! In some of the shots, the cold was easier to ignore than others, but I remember so distinctly when we hit the third shoot of day one (the Navy Dappers), my hands were totally shaking during the entire shoot! It didn’t help that we were right off the water of the harbour, and the wind was picking up, but keeping the fact I was freezing out of my expression was an adventure. My other challenge was my nerves. I’m still a very self-conscious person, and some of the shots were done in really public areas. I was afraid I looked silly or awkward, but once I settled into each persona I was trying to show, it got easier. And once I saw the back of camera shots, I felt so much better.

Tomboy Toes: The three of you deserve some serious props for working through it when the weather was less than ideal. On the flip side, what was the highlight of the photoshoot for you?

Lindsey: Getting Alex and Steph to smile in the photographs. I’m lucky that they’re both easy to work with, and basically just need to get them to smile at each other to get a beautiful expression. I think the best highlight was the shots with the brown Broques, where we could have a little fun and be a little sillier with the umbrella work.

Steph: One of the best things was working with friends (shoutout to Nik and Molly who were the extra hands when it came to perspective and nitpicking clothing folds) but I have to say it was working for a brand that I believe in so heavily and actually seeing its influence on its customer base. Tomboy Toes is exactly the kind of style that Alex wants to have personally, and seeing how much the experience and the product boosted her confidence was amazing. I couldn’t have asked for more.

Alex Perry models the Roguish Brogues in black - photography by Gryfeathr photography. Alex: The highlight of the shoot for me, past working with my friends and seeing everybody, is probably how good the photos made me feel. Considering I was so nervous to represent Tomboy Toes and wanted to do good by the brand name, when I saw the finished photos, I was shocked! Lindsey and Steph were absolute goddesses when it came to making me look good, and the experience as a whole has done wonders for my self confidence, and for that, I’ll always be thankful. I don’t think I’ve ever felt as attractive as I did until I saw the results. I still look at them and I’m so immensely proud of what I helped create!

Tomboy Toes: You’ll have to forgive us for getting a little emotional here. It means so much to hear that (at least for some people) we are truly succeeding at our goal of not just giving people shoes, but giving people confidence. And for anybody being hard on themselves, wondering if they can pull off a more masculine look, all you have to do is take a glance at our model Alex and realize that if someone this stunning was afraid to try to rock the look, there’s nothing wrong with being nervous. You can do it! We believe in you, reader!

Okay, one last question for you all! If you could say just one thing to somebody who likes masculine formal wear but maybe feels a little shy or uncertain about just going for it, what would you tell them?

Lindsey: When you feel more comfortable about what you are wearing, it’s amazing what a difference it can make. Some people may have set ideas about what’s “appropriate,” and that won’t change. But when you feel good in what you are wearing, somehow it isn’t so heavy. Try out with something subtle, something just for you; you don’t have to change completely your whole way of wearing clothes at once! Shoes are actually a great place to start, because people don’t always pay attention to them right away. Adding small pieces, switching out a shirt or jacket, so on, can give you the smaller steps to try out something new until you feel more confident. It’s all about how you feel and what makes you feel good!

Alex Perry models the Roguish Brogues in black - photography by Gryfeathr photography. Steph: Run with it. You do you. Society sure does have some really rigid lines in the way that gender fits in to personal style, and it’s such a load of crap - there’s nothing wrong with wanting a flat, dapper shoe to wear with some dress pants or a skirt! Start small if you’re nervous, like Lindsey said - a little bit here and there can really help. Start with a shoe or a jacket and work your way up from there! Even having a single piece of clothing that fits you and makes you feel fabulous is a huge step, and can really boost confidence. You really deserve to feel awesome, no matter what you wear.

Alex: As someone who has really struggled in the more recent years to come to terms with dressing more masculinely and accepting that it’s okay to not want to dress like a girl and now falls somewhere in the gray of the gender spectrum… Well. The biggest problem for me was always my shoes. I couldn’t dress the way I wanted because I felt that I had nothing to match my pants or the degree of up-do I was trying to produce. The right pair of shoes does wonders, and if you start from the bottom up, it’s great! If you’re just starting to dabble in dressing more masculinely, or don’t know where to start, finding articles that fit properly like a good blazer or a nice set of dress pants is a perfect way to begin. And of course, throw in a pair of Brogues or Dappers to add the pizazz, and you’re set. The biggest obstacle is realizing that it’s okay to want to dress the way you want, regardless of what you fear people might think. You’re going to look good if you’re confident in what you’re wearing, and that’s what I know these shoes are going to help you accomplish-- they’ve done it for me. I wear my Brogues nearly every time I leave the house just to go the grocery store, and it makes me feel about ten times better about how I look!

And there you have it folks! We don’t have much more to add to those eloquent, sincere responses from the incredible team that made the Tomboy Toes photoshoot a reality. We want to emphasize how grateful and appreciative we are that Lindsey, Steph and Alex were willing to take on this project and willing to do this interview for us.

Thanks so much for reading, and stay tuned for more fabulous photos from this trio down the line when the Tommy Classics get their turn in the limelight!

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