Like all growth journeys, I feel like my style journey is characterized by highs and lows. There are weeks where I feel like I really understand my style and am obsessed with my outfits, and then weeks where I feel like I’m struggling to even understand what I like for me versus what I like on other people.
If I’m honest, I think that I’ve been doing too much scrolling and not enough styling, and the truth is it has left me feeling a bit confused. What even is my style? Do I have a style? Do I hate everything I own?
This is my attempt to cut through the confusion of constantly scrolling Instagram and Pinterest to better understand why I’m drawn to different things and how I can incorporate them into my style.
The Approach
Because I’m a big planner, I want to do this in stages. Here’s how I’m going to approach this to avoid getting overwhelmed:
Collect inspiration and analyze what I like about each outfit
Consolidate all of the images and look for patterns
Create a style action plan
Analyzing The Inspiration
For part 1, I started by pulling my recent saves from Instagram and Pinterest. This is where I gather a lot of outfit inspiration but both platforms have been overwhelming me lately. I tried to pick images that are not ‘typical’ outfits I would wear, but I continue to be drawn to.
#1:

What I’m drawn to: It’s hard to tell in this photo but I love the way she has paired some high platform heels with tights. It’s like feminine but with something “weird” or different. I also love the silhouette of the sweater that looks comfortable and effortless paired with an interesting bottom.
What I don’t like: This colour combination is gorgeous in theory but I just know I would never feel like me in it.
#2:

What I’m drawn to: The combination of these very neutral colours in a winter look just gives effortless cool. It’s no monochromatic but a bit “low contrast” so it feels very cohesive to me - nothing jarring despite the fun shoe. I like how the looser fit jeans give it a very relaxed & effortless feel, while the fit of the sweater keeps it sort of pulled together.
What I don’t like: I love the concept of a weird shoe but these ones just wouldn’t work for my wardrobe or my lifestyle. They are a little too girly for me (is there a difference between girly and feminine because I feel like there is).
#3:

What I’m drawn to: I would absolutely wear this full outfit from head to toe. I’m obsessed with the mixing of feminine + masculine (take note of this!!). I’ve also been loving incorporating hoodies into more than loungewear lately. I also love the muted neutral colour palette. It’s not all black but it’s like a low-contrast neutral outfit.
What I don’t like: that I don’t already own a skirt like this.
#4:
What I’m drawn to: Her hair and her effortless vibe*
What I don’t like: I don’t think I would actually wear this outfit, I think I’m really just drawn to her gorgeous hair and the way she just looks so cool!
*This is a perfect example of “love the photo, not the fit” trap that I fall into! There’s nothing wrong with her outfit but when I really think about it, I actually don’t think it would feel like me if I recreated it.
#5:
What I’m drawn to: I love the moderate contrast of this look, the way she has kept it all neutral still feels like it would be me, but it’s not too boring or monotonous. The shoes and way her hair is styled keep subtle feminine or elegant touches that prevent this from feeling TOO tomboy to me.
What I don’t like: Another one with no notes - love it all! I might just add a bit more in terms of accessories (necklace, earrings) but that’s about it.
#6:

What I’m drawn to: This colour palette. Similar to the previous outfit, it’s like a low-moderate contrast neutral outfit but still feels interesting. This specific brown + the dark wash jean is to die for and I love how she paired the deep brown with black accessories - it gives it sort of this like…effortless look (like yes we mix black and brown around here).
What I don’t like: I’m not a big fan of the raw hem jeans or the black boots in this outfit. That style of boot has just never really done it for me, I’d probably do a Mary Jane flat instead but keep them black. Or go more edgy with a chunky black boot.
#7:
What I’m drawn to: This is the perfect juxtaposition of feminine, edgy, cool and effortless to me. The silhouette of the oversized graphic tee + tiered skirt is just SO GOOD!
What I didn’t like: I would swap out the brown boots for black, and go with a slightly more structured or edgy bag (e.g. black with silver studs) to keep it from being a bit too bohemian for my style.
Looking for Patterns
While analyzing one-by-one was valuable, I did start to feel overwhelmed after a while and I found myself just wanting to copy item-for-item rather than truly using it as inspiration.
I found it useful to compile all of the images into one (I use Canvas) so that I could try to see any patterns. It was also incredibly valuable to remove the background on the photos in my collage. This removed any factors like environment or lifestyle that I was drawn to, and really allowed me to focus on the actual clothing pieces.

Looking at these images, I came up with 2 “formulas” that I want to explore further:
Pattern #1: Ultra-feminine + edge + effortless
Characterized by feminine midi skirts paired with effortless graphic tees or sweaters, topped off with edgy accessories or footwear.
One theme I noticed both in these images but also what I tend to pin on Pinterest is the pairing of feminine with more edgy pieces. In the above images, I noticed that it’s a bit of a formula:
Skirt: Sets a very feminine base to the outfit to work around
Lots of volume
Heavier weight fabric
Very feminine details or silhouette
Oversized top: something that just screams “I just threw this thing on” - the epitome of effortless
Oversized sweater
Oversized graphic tee (I love this!!)
Hoodie
Using the shoes to add some edge: created the perfect counterweight to the femininity of the skirt
Black chunky boots (always a staple)
Feminine + weird - e.g. the black lace up flats + white contrasting socks or the super platform heels with the thick tights
Recreating this look:
I sadly do not have a single midi skirt in my closet, and this is something I’m looking to remedy.
In the meantime, I have one midi dress that I’ve worn as a skirt in the past by adding a belt and layering with an oversized sweater. I also have a mini pleated skirt which has been a staple in my wardrobe since the day I bought it.
I tried creating a few outfit combinations for this look:
Ultimately I don’t think I’ve quite captured the vibe I’m craving with these looks, and it shouldn’t come as a surprise that I’ve had “interesting midi skirt” on my wishlist for the better part of 6 months now.
Action Items:
Start actively looking for the right midi skirt to bring into my wardrobe this year. Right now my criteria are:
Must be midi and not maxi (or be tailorable)
Have enough volume or details to capture the femininity that I love about the inspiration photos
Ideally in a dark neutral that is not black - black can feel a bit dark and heavy
Some options I’m currently looking at for a midi skirt are Uniqlo and A Bronze Age.
Pattern #2: Mixing Dark Neutrals
Characterized by mixing dark khaki green, tan, black and grey colours for a more interesting neutral look.
This one is a little less of a specific outfit formula in terms of specific items, but rather provides some set of guidance around mixing neutral colours. I still love an all black monochromatic look, but find that if I do this too often I start feeling a little bit bored.
Mixing darker neutrals is something I was very drawn to in these images - it’s the combination of a dark khaki green + a grey + a black. Or even pairing a white jean with a lighter grey or tan sweater.
Recreating this look:
Unfortunately the only outerwear I’m reaching for these days is my long puffer parka on account of the -15 °C weather, but I’m looking forward to wearing these in spring
Action Items: I’m happy with a few of these options, but I’ve been thinking about adding a casual white pant (maybe jeans?) to my wardrobe to pair with grey or brown. I think this will allow me to add another neutral since sometimes I feel like my blue jeans are actually too blue, and pull the outfit away from that mixed neutral vibe.
Final Thoughts
All in all I actually loved this exercise, and actually ended up almost immediately wearing one of the outfits I created above. While I’m still working on getting more clarity, this helped cut out some of the noise and really solidified for me pieces that I would genuinely get wear out of and feel like “me”.
Have you ever tried to analyze outfit inspiration before? I’d love to hear about how you approached it and would love to try other approaches!
Really love your analysis ! It is an inspiration to me.
As to midi-skirts: there are plenty out there on vintage platforms. Perhaps you will find something not to expensive. 😊
I love the analysis you did to help you understand how you are going to implement back to your wardrobe. Great idea and exercise