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Getting dressed with Courtney Trop

The Influencer and entrepreneur aka @AlwaysJudging

Getting dressed with Courtney Trop

Need help getting dressed? Meet fashion influencer Courtney Trop of @AlwaysJudging. Below, Courtney discusses the power of what we put on each day, how her platform that inspires over 340k followers has gone beyond being only about clothes, and her new CBD company, Stevie.

What was your childhood like, and were creativity and self-expression cultivated in your adolescence?

I had a very interesting childhood, my dad was involved in some illegal businesses and my mom was a secretary. I went to public school in Pittsburgh, PA and most of my peers in my school didn’t really understand my style. My mom and I used to take trips to NYC in the late ’90s and early 2000s so I could find pieces that would be unique to me. Back then remember, online shopping wasn’t a thing. It was more about catalog shopping, or you had to actually travel to find unique things. Being a teenager is hard, expressing myself through my unique style was a way for me to show up to high school every day and have a strong sense of self. I always styled my friends and lent out my clothing in high school. Pittsburgh was really dark for me, and I never really felt like I belonged. My friends were going to the local mall on the weekends and I was getting dropped off in the city and exploring parts where kids from my high school didn’t hang out. Meeting new people that I didn’t see in school every day was always my main focus. Exploring new areas that I had never seen before in more city areas outside where I went to high school in a more suburban setting. The second I graduated I moved to NYC a month after graduation and never looked back. I didn’t keep in touch barely with anyone from high school or anyone from Pittsburgh, I think I just wanted a fresh start. I grew up in FEET of snow, and after a year in NYC, I decided I didn’t need to be cold ever again and moved west.


Do you recall a moment or point when you became aware of your interest in fashion?

When I was three. I wore the same polka dot dress to preschool for a whole week. You would’ve had to sedate me to get it off of me. Ha!

What clothes did you like to wear as a child?

My mom had really good style and was a shopper, so she always dressed me in 80’s style dresses, or all denim. I was a kid in the ’80s and ’90s but Pittsburgh was very far behind so let’s just say a TON of ’80s until I was in high school. I dressed like the Spice Girls a LOT.

Did your parents give you career advice?

Marry a rich man. Where I’m from, women aren’t really working. The man works and the woman has a job to keep busy, or is a stay at home mom. Clearly I did not take that advice and I figured it out on my own! PRAISE! You have to remember everyone in my family still lives in the same township as where they grew up, so this thought process was very common in the ’80s / ‘90s.

A woman in a window wearing a blue bra.


A woman standing in the window wearing blue bras and panties.


We see you as a lifestyle influencer, rather than just a fashion influencer. How do you describe what you do, and what are you trying to impart to your audience?

That’s funny because I always assume my posts are just geared toward styling and how I put myself together, but I guess over the years I’ve shared more so people digest and want more.


"Putting myself together via style and helping others to feel comfortable and like their best self and like they belong via self-expression has always been my thing, so I would say feeding that concept to my audience along with authenticity."

Something I always preach is that I’m not perfect and I would never want to tell people to do as I do, I just share how I live my life and if you see something as a follower of mine that inspires you, GREAT!



Where does the name Always Judging come from? And, are you? Always judging?

I have very strong opinions about style and what I like and don’t like when it comes to fashion. It was intended to be directed on judging clothing and my own personal style what I would wear and what I wouldn’t. AJ has always been my IG handle, even when it was just a personal account with friends, before I started my blog. When I was in search of the name of my blog I just kept the name because I thought it was funny. NO, I AM NOT. Only when it comes to clothing :-)

What do you enjoy most about being a part of the fashion industry?

Becoming a different character every time I get dressed. I didn’t grow up around fancy fashion parties or going to dinners where there were 5 sets of cutlery. When I started receiving invites to these types of events, attending made me feel really out of place and it was hard for me to speak with people who I looked up to that intimidated me.  Putting myself together in a certain way and becoming characters via my style helped me walk into a room and feel like I had a strong sense of self.  Also, CBD and cannabis help with my nerves and any type of social anxiety. Now I absolutely feel comfortable and I love being in a room full of people that inspire me and have the same interests and love for fashion. Fashion has saved my life in a way, any time I’ve struggled with depression, being involved in this industry has pulled me out.


Can you tell us about a favorite project or collaboration?

Anything with Gucci. I love everything the brand stands for and their ability to bring up people who are misunderstood in some societies and the way they celebrate what could socially in the past, be looked at, as a flaw. Gucci is ahead of the industry in so many ways. As a blogger, brands play with your head sometimes and you never know every season if you’re going to be invited back to a show, or if you’re going to be included in projects that season. When you’re part of the Gucci team, you’re part of the family for good. They are consistent as a brand, and they respect me in our relationship. Any of my projects or shows/events that I’ve been part of would be my answer.

How do you deal with trolls and unnecessary nonsense from people on the internet?

Normally I don’t feed into it or spend too much time thinking about things like this because I know negativity comes from a place of insecurity and unhappiness. Most of the time when someone says something hateful it has nothing to do with me, but more-so them. This is transparent because I know when I’m upset about something I need to look within to figure out where my anger comes from. I used to respond to negative comments, but I recently decided to not put any energy into them because the people who send them don’t truly know me. There’s a lot more to me than what I share on the internet.

A woman wearing white lace lingerie.

We know you love vintage clothes - is there a particular period, piece, designer your hunting for right now?

Wearing only Issey Pleats Please lately. LA is casual!!!!! Replika and Scout are two of my fave vintage stores in LA. Ohh also Aralda vintage.


Is there a particular time period in fashion or subculture that you feel a special kinship with stylistically?



Can you describe the outfit that you feel the best in?

I prefer two-piece sets. Anything that comes in a set with a top and bottom, it makes life easier, especially right now! My fave thing in my wardrobe in a two-piece Jean Paul Gaultier Cyberbaba Optic Illusion trouser and pants duo from 1996.


What three words would you use to describe your personal style? 

A little harder, sometimes goth, sometimes I can wear a power suit and come across more refined, but I would really like to focus on the fact that I like to become a character when I get dressed.

Is there anything you would like to share with us about how you chose to take on this Lingerie On Film?

Araks is MY absolute fave undies and I’m not just saying that!!!


Can you share a story about shooting your rolls?

We just went into lockdown in LA, so I basically shot the entire thing in my house with my partner, just trying to make use of the modest space we have in LA in our home. The backyard is the bonus of this house though, so we had a lot to work with!

Speaking of COVID, what have you been up to since lockdown?

Working on my CBD brand Hi Stevie, taking mushrooms, trying to stay afloat mentally and physically. DOING A TON OF HOT YOGA. My yoga instructor is still offering privates so that has really kept me going.

A woman from the back with panties on her head.

Stevie sounds very exciting and fun, what's the story?

Cannabis has been in my family for a very long time. I decided I wanted to start a brand, something thoughtful to offer to my followers that felt somewhat proactive alongside wellness. My career as a fashion blogger is very important to me and I never thought of myself as a designer so I wanted to do something different that didn’t compete with my fashion career, something that would even complement it. In fashion we don’t get much sleep during fashion month, things are last minute and seem stressful sometimes, there’s a lot of socializing-social anxiety, traveling, etc…. To be able to function in this industry, I smoke cannabis and take CBD. This was the perfect idea to also help everyone else, not just me! I felt there was a huge gap since I’ve spent the last 3 years mainly in Europe, but my home base is Los Angeles-where Cannabis and CBD are HUGE. I wanted to start talking about the benefits of CBD in these other places and specifically in the fashion industry.


Why a CBD company?

I’ve been openly smoking cannabis and taking CBD on my IG for YEARS, so my followers know this is something that is authentic and I know a lot about this industry, I’m not just selling something random just for the pure idea of starting a business and making money. Money is a HUGE driver for me with Stevie, only because I need it to launch other products, and build this world of wellness for people.


What was launching a new company in the beginning of a pandemic like?

Seems like a time when we need all the help we can get with our overfraught minds. There have been pro’s and con’s to launching in 2020. A positive is the fact that I have way more time to properly focus on building a brand and CBD promotes a healthier lifestyle and a healthy body and mind-exactly what we need right now! Cons are the fact that it’s hard to produce, have shoots, etc…


CBD is such a large market now, what's special about Stevie?

This is interesting because I don’t think we have any competitors and I also don’t really pay attention to anything anyone else is doing because I like to just keep the branding and product close to my heart and home and do things I think work for myself, not based on what anyone else is doing. As far as competitors go, there are a few other brands with good products but when it comes to branding nothing has specifically stuck out to me that I’ve seen. People are honestly still weird about cannabis and CBD so I wanted to brand something that felt more like what we’ve seen in beauty and skincare but also a product that truly worked well, and something I would actually want to personally take above anything else. This is why I personally don’t think I have any competitors because I made my own perfect CBD that works for me! Now if you ask someone else I’m sure out of all the CBD users in the world, everyone will have different opinions and different brands they like. Like you said, it’s a large market! Another side note is, we are asking our community for advice on every product we launch. Feedback and giving the Stevie community what they want, and listening is very important for us.

Woman wearing red and blue lingerie with panties on her head.

Woman wearing layers of different color lingerie.

Could you give some tips on what to look for and what to steer clear of when shopping CBD products?

Personally, organic carrier oil-organic MCT oil, something that is derived from coconuts, not palm leaves, 3rd party lab-tested. Research that the CBD is coming from a trusted source- research the company, look at reviews…. Trial and error honestly right now are very effective. CBD is still new, it’s only been around for a little in the grand scheme of time. You really need to try things and figure out what works well with your body. Oh lastly- I don’t like artificial flavoring. Ours is natural.

What's next for Stevie?

Pre-rolls, Body Salve, Edibles, Candle, Bath bomb. We’re opening a Stevie Pop-up for the holidays at Platform in Culver City.



Any fun inside recommendations? Or safe outside recommendations? Hiking, micro-dosing mushrooms in a park :-).

Dream collaborator - dead or alive?

What is something you've loved for a long time?

What is something you would love to learn?

What's the best piece of advice you've been given?
  Don’t force anything on anyone.

Can you share a favorite quotation, lyric, or line from a book or song that has stuck with you?
  I have no fear I have only love. Fleetwood Mac, Gypsy.

What is something that you feel is overrated? Underrated?
  Being unhappy. Focusing on yourself and being happy!!

Is there anything you could recommend to us?  

What are you terrible at but love to do anyway?
  Sing.. lol

Can you tell us a joke?
  No but my favorite SNL skit is the one where they all get abducted by aliens with Ryan Gosling.

Hidden talent?
  I can see any movie and tell you everything the actors have ever been in even if it was 60 years ago and they were a baby.

Can you fill in the blank? - Beauty is... 
in the way you carry yourself!


Thank you, Courtney!

@alwaysjudging and @hi.stevie

Creator of the once beloved retailer Anaise, and now HÉLÈNE, a creative studio offering photography, styling, creative direction, and model management.
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