"We Use Clothes & Makeup As A Lifesaving Form Of Self-Expression."
Style Questionnaire with Leo Aquino of Queer & Trans Wealth
Leo Aquino, 32, is an award-winning independent journalist and financial coach at Queer & Trans Wealth and he also writes the
newsletter.
I started following Leo on Instagram, where posts like this one got me thinking. As I was reading and learning from Leo’s wisdom, his enviable sense of style really stole my attention. It was eye-catching and a little flamboyant but also very put together. Fun! And also carefully considered and polished.
Leo also hosts amazing workshops like this upcoming one using a psychotherapy approach called Internal Family Systems to teach anti-capitalists how to receive abundance.
What are you wearing right now?
I’m wearing a pair of thrifted plaid pants, a bright orange t-shirt with some art by Keith Haring, and purple glitter house slippers that I got from the Dollar Tree.
What was the last item of clothing you bought?
I bought this gorgeous corduroy jacket from a brand called Fortune W.W.D. while I was in Manila. It’s made of Japanese corduroy and has incredible chain stitching. It just so happened that the store was having a moving sale while I was visiting Manila and everything was 40% off. This was definitely over budget, but it was too good to pass up!
Having a budget for clothes is so important. The budget isn’t meant to be restrictive, but it’s meant to be like, “Okay, no matter how tight things get, I’m setting aside $50 to buy one nice shirt or pick up a few things from the thrift store because that’s what my gender needs.” I always advise my clients, even if it’s as little as $5 or $10, just put something in the “gender-affirming non-negotiables” category of your budget to take care of yourself.
I’ll let myself say “fuck it” and spend money outside my budget on clothes when I’m traveling. This trip to the Philippines was really special and I wanted to make sure I had some pieces from Filipino designers. The Japanese corduroy jacket was the last one of my size in store! Come on! It was meant to be.
I want to publish more of these Style Questionnaires! Please consider becoming a paid subscriber if you want to read more.
How do you think about spending money on clothes?
I’m definitely a deal hunter and thrift shopper. I have a tailor at a swap meet about 10 minutes away from where I live. So a lot of times, I’ll buy something on sale or thrifted and I’ll spend $10-$30 getting something tailored. I will splurge every now and then on a one-of-a-kind piece!
A lot of times, personal finance experts will tell people to cut back on things like clothes and makeup, which are considered discretionary spending. For queer & trans folx, we use clothes and makeup as a lifesaving form of self-expression. So I encourage people to prioritize some money—even as little as $10 to spend at a thrift store—for gender-affirming non-negotiables before debt payoff goals or savings goals.
If you had to wear a uniform (same thing every day) what would it be?
When I visited Tokyo, I went to this store called GU, a sibling store of Uniqlo, looking for a hoodie to wear on the plane ride back. For some reason, they didn’t have any hoodies with long sleeves on them. There were only sleeveless hoodies and short-sleeve hoodies and I giggled while putting a few in my cart. I thought it was really silly at first, but man, I look really hot in a sleeveless hoodie! The sleeveless hoodie makes my body and face look really square while showing off my arms and tattoos. (similar up to men’s 6XL and similar up to 4x)
Where did you get clothes as a kid? Describe a favorite childhood outfit.
I grew up in Manila, and I used to love this store called Penshoppe. I was also obsessed with Mandy Moore and she had a HUGE Filipino fanbase. Penshoppe used to give out free Mandy Moore posters if you spent a certain amount in the store. So I would buy stuff from the store just to get the posters.
As a kid, my mom dressed me up very nonbinary, in my opinion, with lots of bright colors, patterns, onesies, and matching sets. As a tween, I was definitely more of a raccoon eyeliner, slogan tee kind of “girl” with jeans, a studded belt, and platform Sketchers flip flops with a star cutout in the heel.
Tell me about an item of clothing that you wear only to do a specific activity.
I am building a rotation of suits with vibrant colors for conference and business events! I call it my corporate drag, lol. (similar up to size 32, similar up to 24, similar up to 3x, Similar up to size 40)
I’m going through a big shift right now. I’ve always worked in start-ups and corporate spaces, but I am committed to working for myself for the next 3-5 years. This path is not for the weak. I attend a lot of business and journalism conferences to get mentorship, tools, and support while I build Queer & Trans Wealth. I have a ton of impostor syndrom—but a great outfit really helps with that!
It’s funny, the last job I quit in December, my boss told me he was disappointed that I’m quitting. After that, I went to a drag show to support a friend’s girlfriend. And the drag queen hosting the event had the crowd chant, “DRAG IS DISAPPOINTING!” That’s when it hit me that being in corporate spaces is my own version of drag. I love a good suit, and it’s definitely my version of drag.
Shopping for suits is soooo hard, but the payoff is worth it. If it doesn’t make you dysphoric, I recommend plus-size folx shop in the section you were assigned at birth —for example, I shop in the “women’s section.” (See? Drag!) I would buy something on sale at Macy’s or wherever and just invest in a good tailor that can make gender-affirming adjustments for you. I have the privilege of having gone to fashion school, so I tailor my own suits—but here are some changes I typically make:
Shorten the sleeves
“Women’s” jackets typically have darts or seams that make space for the sandbags/chichis/titties, so I would ask your tailor to take those out and flatten it if you’ve had top surgery
Shorten the pants—they should hit the bottom of your ankle so you can show off cute socks
Take the extra fabric from the pants and ask your tailor to use it to add 1-2 inches to the waistband to give you more room for your belly!
What does Queer and/or Trans style look like to you?
Bold. There’s no one way that queer/trans people dress but we always own it!
What did you wear to the last party or event you attended?
I put together a bunch of cute outfits for the Queer Rhapsody film festival here in LA!
One night I wore a red dress I thrifted from Plus Bus with a gold necklace.
My girlfriend and I wore matching Brat green dresses to a screening of Darby and the Dead—if you can find this online, please stream it! It’s soooo good. My Brat green dress was also thrifted from Plus Bus and I paired it with my favorite two-tone blue denim jacket, which I got in Albuquerque.
I wore this printed 2-piece printed set from Target one night. (similar set here.) Queer Rhapsody was such an inspiring film festival — and a fun excuse to dress up!
What do you wish you had in your wardrobe that you don’t?
A baby blue linen suit.
One: I’m obsessed with linen and I love ironing, haha. I think linen is such an effortless and breathable fabric. I want the suit to have clean lines and immaculate tailoring, especially since linen doesn’t really stretch. I want the pants to have an elastic waistband, but to still look like sharp, tailored slacks. I want it to give black sheep, Silicon Valley uncle in early retirement using his riches for good, lol. And I’d pair the suit with a ripped white tank top and cool, colorful sneakers instead of a rich-guy loafer.
Two: I was hospitalized for mental health reasons in 2019 and I had to wear this baby blue hospital pajama outfit. This was obviously a dark time for me, but I remembered thinking, “Wow, I look great in baby blue.” So now I surround myself with some baby blue home decor and incorporate baby blue into my wardrobe to reframe and reclaim that experience.
(similar up to 4x, similar up to 3x)
Tell me about an experience that changed your relationship to clothing or getting dressed.
Growing up, I’d say my body has been mid-sized with a giant rack—up until my top surgery in 2021, of course.
Before top surgery, I wore black all the time. My go-to was black leggings, a black turtleneck from Uniqlo, a gold nameplate necklace, and white sneakers. So when I took pictures, I literally looked like a floating head. I was so unhappy and constantly depressed. There was a huge hit of euphoria after getting my top surgery and my shirts and tops lay flat. I rarely wear all black anymore because I genuinely love getting dressed and have my picture taken!
One thing that hasn’t changed for me is that I love having a capsule of pieces that I mix and match. I’m quite minimal and I have a ton of extra space in my closet. I’ve been like this since before top surgery. The challenge with hormone replacement therapy (I’m on T) is that my weight goes up and down so much, and it can get dysphoric when some pairs of pants that I love, that I went out of the way to get tailored, don’t fit me anymore or pinch my tummy and give me that little crease in the middle.
It’s a mixed bag, for sure!
Tell me about an accessory or piece of clothing that you lost or ruined but still think about.
I get so intensely attached to my clothes! I bought a men’s pistachio green waffle knit hoodie on sale at Everlane (similar up to XXL) and it just fit me so well and the color really made my skin pop. I was leaving for an early flight out of San Francisco and I left the hoodie in the hotel room. This happened in October 2023 and I’m still soooo so sad about it!
What’s your 2024 summer must have?
Men’s swim trunks with a tiny 3.5” inseam. My girlfriend calls these my “little gay boy swim trunks.” (similar up to XL, similar up to 6x)
Who do you think has good style?
My Tito Onet is my current style inspo! His style is inspired by the K-dramas he watches, and he’s a big time sneakerhead. My family and I have a little ritual of going to this dim sum place in Queens called Asian Jewels, then we’ll get bubble tea around the corner, and hit up the Nike outlet as the last stop. I always look forward to the sneakers that Tito Onet picks out for me for gifts & holidays!
Anything else you want to tell us about getting dressed?
Find a good tailor! This is actually advice that Tan France gave me when I interviewed him for an article in 2022. I have a tailor that my sister-in-law introduced me to, and I know how to tailor myself. If you don’t know how to sew or don’t have a sewing machine, I really recommend taking a class and learning how to sew because it opens up soooo many options for outfits and it makes me feel so good and hot and fancy to wear something that has been tailored.
Thanks, Leo! Follow Leo on Instagram and subscribe to and consider signing up for this upcoming class!
This post contains affiliate links.
 | A guest post by
|
Leo's choice of color is striking and gave me a wee bit of courage. In honor of the chartreuse outfits, I had a manicure this afternoon and now have chartreuse fingernails. And definitely Yes to the Japanese corduroy. I loved this interview.
I’m obsessed with that 2 piece set from Target. Also, love all the color. Thank you, Leo.