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How To Use Edgy Modern Prep Style To Express Yourself - Interview With Fashion Blogger And 100 Most Stylish DapperQs, The Pocket Tomboy




LH: Let's start with some Rapid Fire questions. In your own words, who is Pocket Tomboy?

PT: Haha! What a deep question to start off with! I guess on the surface I would say that I’m a type of person who doesn’t take things too seriously. I’m a “glass is half full” type of person who uses humor to get through the difficulties of the day.


LH: What is the biggest misconception people have about you?

    PT: Probably that I’m actually older than what I appear to be. I still get carded when I buy beer, I still get asked “what school do you go to?” when I graduated from college 8 years ago.


    LH: What is the one thing that most people don’t know about you?

      PT: That I have a black belt in Kenpo Karate. I was big into sports as a kid and I made it to black belt when I was 9 years old, but then my interests shifted towards music so I stopped being involved with martial arts. As for fashion, most people wouldn’t believe that I own a pair of Crocs and wear them almost every day when I’m lounging at home or washing my car.


      LH: What do you do for work?

        PT: I work as a PR Executive for the hospitality industry and I’m also a Content Manager for a trade magazine for the same industry.


        LH: What would you ideally do?

          PT: I want to get back into entertainment again. For several years I worked in the entertainment industry as a writer and I really miss that type of work. Ideally, I would love for my next career opportunity to blend fashion, music, and writing.




          LH: What does fashion mean to you?

            PT: Fashion is something we deal with and work with every day if someone claims they don’t care about fashion, they actually sort of do, because there are reasons why someone chose to wear what they’re wearing; even if that just means it’s comfortable and it washes well.  For me personally, fashion is the ultimate way to express myself and my identity without having to speak. The clothes I choose to wear have a purpose, and that purpose is to feel powerful and confident, but approachable.


            LH: How and when did your interest in fashion begin?

              PT: I’ve been into fashion as far back as I can remember. According to my mother, when I was two-years-old and Santa asked what I wanted for Christmas, I said I wanted “an outfit”.


              LH: Why is fashion important to you?

                PT: Fashion is important because it’s another way to express who I am and what I’m feeling at the moment.


                LH: What did it feel like to see yourself on the DapperQ 100 Most Stylish Class of 2017 list?

                  PT: Being named one of the 100 Most DapperQs of 2017 was an incredible honor. At the time, I was relatively new to the whole “queer fashion Instagram world” so to receive that distinction as a newcomer was pretty awesome.




                  LH: How would you describe your personal style and aesthetic?

                  PT: I would describe my style as edgy modern prep. I’ve always been drawn to traditional prep attire and the brands associated with that aesthetic; growing up in New England certainly helped mold my love for old-school Ivy League style as well.


                  LH: How do you select your outfits?

                    PT: I’ve always planned my outfits the night before since I was in middle school and I still do that. I live in Florida, so pretty much all the time I sacrifice comfort for style; kudos to the folks who wear shorts, flip-flops, and tank tops every day, but that is not me; I’d rather sweat it out in my selvedge denim and an oxford shirt.


                    LH: How has your sense of fashion and style evolved over the years?

                      PT: Oh my, my sense of fashion has evolved quite a bit! But it really morphed when I came out as gender non-conforming/transmasculine. There was a period of my life from around 13 to 26 where I was trying so hard to be femme; skirts, wedge heels, pearls...you name it. I’ll spare the readers the details of coming to terms with my gender, but thinking back, even when I was “playing femme” the items that made me feel good and made me feel more confident were on the masculine spectrum, like schoolboy style blazers.


                      LH: Which designers, brands or people have influenced your style choices? How and why?

                        PT: I’m not really loyal to one brand or designer, but my favorite would have to be Ralph Lauren. I’ve consistently worn Ralph Lauren throughout my fashion and gender journey. I love timeless, preppy pieces that can be worn in multiple ways. As for style inspiration; I’ve been looking at David Beckham for years (maybe not when he had cornrows haha) and love how he combines classic pieces but then works a bit of an edge to his outfits. I’m also inspired by ‘60s mod fashion. Slim silhouettes rolled up jeans, fitted Fred Perry polos.




                        LH: Where do you shop?

                          PT: I love looking at discount places like Marshall’s, TJ Maxx, Nordstrom Rack etc. I’m a bargain hunter and these places, you never know what you’re going to find. I also love UNIQLO for basics; their selvedge jeans are probably one of the best buys you can get if you want to get into raw denim.

                          Lots of people just assume that I’m throwing tons of money at clothes, and I tell them that I don’t pay full price for ANYTHING. I once got an in-season Rag & Bone oxford that retails for $250 for like $20. I’ve purchased Chuck Taylors at Converse outlets for under $10.

                          One of my most expensive purchases was a leather bomber jacket from Coach. It was $1500. Like hell, I would ever spend that much money on a piece. I waited for several months and then it went on sale for 75-percent off even then I was like, “Ehhhh do I need to spend THAT much money?” but there was only one XS left and I just splurged.


                          LH: What brands have you found fit your aesthetic and body type?

                            PT: My wardrobe is 99% menswear and as someone who is much smaller than the average AMAB person, let alone AFAB person, clothes aren’t simply made for smaller dudes. However, besides tailoring I have found multiple brands that fit me well off the rack.

                            Believe it or not, I’ve been really into Abercrombie & Fitch lately for oxford shirts and pants. Since they fired their horrible CEO and rebranded, their pieces have been great quality-wise and fit well (their men’s XS is a true extra small and they offer shorter inseam pants).

                            I also love Original Penguin; again, their clothes are more fitted, and I love that they add fun details. I have a pair of chinos from them with little robots and rocket ships all over them, I have a shirt with mix tapes on it.

                            ASOS is also a great resource for smaller folks because a majority of the menswear they sell go down to XS and even XXS.


                            LH: Do you prefer shopping online or in store? Why?

                              PT: Honestly, I like shopping online and in store. Sometimes it’s hard to find smaller sizes in store, so I end up ordering online and if it’s a brick and mortar retailer I end up having it shipped to the store because it’s cheaper, but then I usually buy more when I GO to the store.




                              LH: What attracted you to HLD - Light and why did you decide to collaborate with the brand?

                                PT: I wanted to work with HLD - Light because I like working with indie brands and helping them get recognized. The big brands don’t need help, but indie brands, especially indie queer brands don’t have the extensive financial resources the big companies do. I was also drawn to the minimalistic aesthetic of HLD - Light.


                                LH: You chose to showcase The Signature HLD Black Puzzle Shirt. What stood out to you about this particular design?

                                  PT: What stood out for me was the minimalistic design and message. It’s a conversation starter and I like talking to folks about my clothes and the meaning behind them.


                                  LH: What are your favourite ways to style and wear this T-shirt?

                                  PT: I don’t like to “busy up” outfits when I’m wearing a graphic tee like I wore for HLD - Light, so I made it the focal point and simply paired it with dark indigo denim and light denim cut-offs for a more casual look. Since it’s getting a bit colder, I’ve also worn it under a leather moto jacket.


                                  LH: What advice do you have for other fashion enthusiasts who are still experimenting with and searching for their own personal style?

                                    PT: Keep experimenting! Sure, I’ve found out what “works” for me style-wise, but I’m still figuring things out. I’m guessing there’s probably something in your closet now that you bought because you really liked it, but you might be too self-conscious to wear it for whatever reason. My advice? Just wear it.




                                    LH: Why did you start a fashion blog?

                                      PT: I honestly started blogging and documenting my outfits and style on Instagram as a New Year’s Resolution of sorts back in 2016. I was never one for selfies or taking a lot of pictures, but friends enjoyed my style and were like “You should do an Instagram page blah blah.” 3 years later, I didn’t think I would have brands reaching out to me to promote their products, but now they are and it’s pretty awesome.


                                      LH: As a successful fashion blogger, what advice would you give to someone looking to start one of their own?

                                        PT: So if you want to start documenting your style on Instagram I have a few tips. Make sure your photos are well-lit, utilize appropriate hashtags, and don’t skimp on the photo text! Also, know what your personal brand identity is. My persona on my blog and instagram page is exactly how I am off social media. If I started posting “inspirational quotes” and moody black and white photos instead of the light-hearted stuff I usually post, my followers would be like, “What the hell is going on with them?!”


                                        LH: What is the best way for our readers to learn more about you or to get in touch with you?

                                        PT: My Instagram and my Blog are the best ways to do that right now. 


                                        LH: Final question, how many shoes do you own?

                                          I definitely lost count with how many shoes I have, but it’s around 100 pairs.


                                          Did you enjoy this interview? Did you find the Pocket Tomboy's styling tips helpful? Whom would you like to hear from next? Let us know in the comments below - we'd love to hear your thoughts!

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