I’ve had a few requests to write an All That She Wrote on personal style and how to figure it out, and believe me, I’ve tried. Personal style is such a broad and varied topic, and I genuinely do not feel like I’ve got it figured out myself!
A few months ago, I wrote a piece on my personal style journey. I took readers through my varied phases of personal fashion starting with high school and ending in present day. What I gained through my photo research is the discovery that there are some through lines!
Since age 15 or so, I’ve loved putting an outfit together! In high school, my outfits were mainly inspired by other fashionable girls at my high school and Teen Vogue magazines with the occasional inspo from someone in my youth group (hello Toms mania).
Pinterest didn’t yet exist, and even if it had, I didn’t get a smartphone until graduating high school (specifically, the iPhone 4 I purchased with graduation money in 2012). My fashion inspo had to come from images or muses around me or the stores I had access to in my town. My personal fave was a local boutique called AzWell. Any Flowood, MS alums remember that one?
When considering my personal style, I never feel like I can really define it without considering what I’m enjoying at the specific moment in time, and I don’t think it has a specific title (modern, boho, eclectic, etc.). But where does that leave me over the past 15 years? Again, I think it’s important to consider those through lines.
I’d say since discovering ~fashion~ in high school, I’ve always enjoyed dressing in color. Two pieces that stand out to me specifically are a pair of purple corduroy skinny jeans I got from a Delia’s catalog my freshman year and a mustard yellow H&M mini skirt I found a thrift shop in Jackson, MS called The Orange Peel.

Though my fashion interests wax and wane (#neverforget the great trendy plight of 2020), I’d say that color has always intrigued me. So where do we go from there? Maybe this one through line is a good place to start, but what else? My style isn’t solely defined by being colorful.
In 2021, I got really into Amy Smilovic of Tibi’s reels/Instagram stories on how to find your personal style through a set of three defining style words. Her words are “chill, modern, and classic”. When getting dressed or shopping for new items, Amy always has these three words in mind. Can this outfit be defined as chill? Does it look modern? Does it have classic elements?
Finding my style words was a helpful place for me to start when considering my individual style in the 2020’s. I don’t always think through them when getting dressed, but I think it could be a helpful place for some folks to start. I also think having some style words can help us be a bit more mindful when shopping for our wardrobes! If you’re curious, my words are structured, feminine, and creative.



Here are three pictures from ‘22, ‘23, and ‘24 respectively. I think to each one there is a structured element (a vintage jean, a fitted blazer, a pleated skirt), a feminine element (a gingham PJ top, a flattering silhouette, a Mary Jane shoe), and a creative element (a tie dye sock, the Staud bucket bag, a denim chore jacket paired with preppy pieces). Now, does that mean I can only dress to these three words? Absolutely not. I daresay the outfit I’m wearing while writing this Substack might not have a specific “feminine” element to it other than my makeup or hairstyling (which counts imo). Again, these “style words” can be a good place for fashion-curious folks to start!
So what does that mean for you? Well, maybe start by asking yourself, “what are some things I like about my style? What are some things I like about myself?” Maybe you’re really athletic, so maybe your word for that is “sporty”. Maybe you’re really brilliant, so you choose the style word “smart”. Maybe you’re quite a relaxed person, so your style word is “chill” like Amy’s. If you find yourself feeling stumped, reach out to a close friend or a relative and ask them if they’ve noticed any defining elements of your personal style! They might be able to weigh in on your ‘fits in ways you can’t see yourself.
Another way to get started on defining your personal style is with a styling challenge! Mandy Lee of Old Loser in Brooklyn does a styling challenge at the start of every year in order to help herself hone in on her personal style and get her creative juices flowing. I participated in the challenge this year (up to day 65, that is), and it was a really great way to flex the creative outfit mind and hone in on my personal style!
The challenge consists of a few rules: get dressed every day, no shopping, document your daily outfits, set personal goals, etc. She challenges participants to use Pinterest and Instagram sparingly when creating outfits. The point is to push yourself in your own wardrobe without leaning on new pieces or inspo from the outside world!
For anyone looking to discover their personal style or become acquainted with it more deeply, this challenge (or even a similar 20 or 30 day challenge) as well as choosing some style words are where I suggest you start! Personal style is ever-evolving and difficult to define, but there are ways to tune out the new-trend-noise and focus on what you relate to personally. Harling Ross Anton had a Gumshoe Substack on this very thing! It’s currently behind a paywall, but if you’re already a subscriber, I suggest giving it a read.
Like I said before, I don’t have it all figured out, but I hope this gave you a good place to start! Getting dressed should be fun, not something that feels like a chore (though it’s natural to have those days). I hope getting dressed can be exciting for you in the days to come!
And that’s All That She Wrote today, folks! Happy styling!
-Anna Kristen
what three words would you use to describe my style?
- Gyatthew