How I decide what to wear
Enter my mind if you dare - this is a long but good one!
According to the internet (and a quote from this HBR article I read on a new favorite book “The Artist’s Way”) we make on average 35,000 decisions each day, including what we will eat, what we will wear, what we will say, and how we'll say it.
Today many of us are focused on decreasing those decisions particularly when it comes to food and clothing. And many brands use this statistic as justification for driving us down the path of outsourcing our thinking for the sake of convenience, simplicity, etc. (see companies like doordash, hello fresh, aday, vetta)
Maybe that convenience and simplicity speaks to you - and to a degree I think it does for everyone - but personally, I find that it leads to a slow (and then all at once) slide into becoming disenchanted, uninspired, and just plain bored with my wardrobe. Where’s the spice? Where’s the flexibility?
What if Thursday me wants to deviate a bit from my uniform and try something unexpected that might work or might not? What if the weather swings to a balmy 75 degrees in the middle of March and I want to play with atypical combinations of my clothes (say a thick wool sweater with some snakeskin sandals)?
I’ve come to realize that there are so many personal parallels for how I approach what I eat and how I decide what to wear. For me, I don’t view preparing a meal or getting dressed as a chore… instead I find so much joy in these choices. I get to scour the grocery store or farmers market for the whatever produce and meat looks best (usually what’s local and in season) and put together a yummy dish (side note processed food is the fast fashion of the culinary world).
I’m okay with repeating a favorite dish over and over but to eat the same meal day in and day out sounds like a nightmare (maybe this is reminiscent of my school uniform days - that I get to pick what I wear every day is wonderful to me).
If you are someone who wants to make little to no decisions and have prescribed outfits or items “everyone should have in their closet” - then this is likely not the article for you.
If however, you like the idea of having the equivalent of your own pantry staples, spice cabinet, etc. in your wardrobe that give you the freedom and flexibility to adapt to your lifestyle and daily taste - then keep reading because you’ve found a kindred spirit who can give you some fresh approaches to getting dressed everyday.
This is not coming from a place of judgment, but if something appeals to all then it also appeals to none - and choosing to be individual means you’re not going to nail it or resonate with everyone, all the time… and… isn’t that kind of the point of personal style? It should uniquely appeal to you.
Controversial opinion: I loathe capsule wardrobes
Going to continue with the cooking analogy here - to me there is a difference between having some go-to dishes or even pantry staples vs. meal prepping on Sunday to eat the same meal for the next 5 days this week and maybe the next 8 weeks after that (sometimes I envy those who can do that routine, but for me it just leads to stale uninspiring food by day 2 and IMHO life is too short to eat bad food or wear a blah outfit by design).
So what’s the alternative? Surely we can’t be expected to make all our meals outfits from scratch… right?
You don’t need to start from scratch but you do need a starting point
This is the part where I’d love to introduce some magic formula or framework, and there are some out there that I appreciate, admire, and leverage at times:
Amy Smilovic’s Creative Pragmatist sliding scale
For me, there is honestly no one day that I approach 100% the same - rather there are a few ways I think through getting dressed for the day. These are the (4) that I turn to most often and usually in a combination (because why not?)
1. The Interviewer: Who/Where/What/How
Who do I want to be today? aka which facet of myself do I want to play up?
Where will I be? this is more than just location, it’s also the weather to activity, setting, or even the day or night’s vibe
What must I wear today? newest addition? and old favorite? a sentimental piece to remember a beloved grandmother? a piece that I just can’t get enough of right now? a piece that’s one of my least worn? is there a dress code I should take into account?
What’s available/unavailable - this could be anything from something that’s at the dry cleaners to a gap in my wardrobe that I need to work around
How am I feeling/how do I want to feel - daring? exhausted? uninspired?
If you recall one of my first posts on substack about the power of accessories - often I start with the ‘what’ questions and build my outfit around that accessory (usually jewelry, shoes, scarf, hat, bag, etc.) while taking into account where the day will take me and which version of myself I want to be that day.
2. The Stoic: uncontrollable vs. controllable
A simpler but more freeform version of this approach is to sort all decisions into two buckets, starting with what I can’t control followed by what I can:
Not my choice:
Weather - if it’s hot or freezing, I have to accept and dress for the elements
Dress code - if I’m going into the office or to a wedding, there are often limits to what is ‘acceptable’ (this doesn’t mean rules cannot be bent, or never broken)
Available items - what I have is what I have, unless I’m planning ahead for a trip - cannot supplement my wardrobe in the morning
Daily demands - am I going to be out all day and need more utility from my bag? will I be on my feet and want my shoes to be more comfortable?
Totally up to me:
What colors I wear
Silhouette of the outfit
Accessories
Hair/makeup
Discomfort tolerance
3. The Home Cook: recipe + adjust
Think of this as a starter kit on your path to the chef - essentially you save/are inspired by a recipe and adjust based off what you have at home (fridge/pantry), your allergies (aka style icks), and preferences (to taste!)
You may start by copying the recipe outfit exactly as is but overtime you’ll build the confidence to pull out what you like and leave what you don’t. You’ll realize which ingredients, cuisines, and methods you gravitate towards over time and lean into those. For me, I’m a pants and top person and I rarely wear skirts. I have also realized that I don’t love overtly feminine or dainty things. I can appreciate them on others but they are usually a no for me. In the same way that I love the flavor of mushrooms but am picky about how they are prepared because the texture is a major ick for me.
Some of my favorite sources for recipes to try:
Ralph Lauren (just purchased a coffee table book about him titled, In His Own Fashion, genuinely love turning to stylish men for inspiration)
Alain Delon (French actor who dressed impeccably)
Paul Newman
Faye Dunaway (have been obsessed with her as a style icon since I saw Bonnie & Clyde)
4. The Chef: pantry staples + what’s in season + cravings
This is a personal favorite because it is what I think capsule wardrobes try to emulate but (for me anyway) fall as flat as a grab-and-go airport salad (gets the job done but is more of a lowlight than a highlight of a trip).
I could probably do a post on this approach alone (if not more - will consider this for a future post assuming interest) - but here is one example to illustrate this approach:
Pantry Staples
Think of what are the bases (not basics) in your wardrobe. These are like the milk, flour, eggs, and butter of your wardrobe - you can use them to make bread, pasta, French toast, almost any kind of base for nearly any kind of meal. Pairs well with most proteins, vegetables, and even fruit! Can be simple or decadent - depending on how you prepare it and what you pair it with.
Most people likely have a white tee and a pair of jeans in their wardrobe. What’s different is the kind of white tee and jeans — think varying shades (shades of white, or washes for the denim), proportions (more oversized vs. fitted, long vs. cropped, etc.)
There are no right pantry staples - there are only the ones that make sense for you and your lifestyle.
What’s In Season
This is what is available/best for the time of year wherever you are. This is where layers and occasion (and some accessories like scarves, hats, shoes, or lack of come into play).
Cravings (aka needs + wants)
This can begin with the previous category of what’s in season…
Maybe you need a light layer for the day but you’re craving a khaki blazer instead of a denim jacket or a long cotton trench coat
Maybe you need to keep your feet warm but you’d rather be more comfortable in a pair of uggs than booties with a 3-4 inch heel
Maybe black is feeling too stark for you today and you want to soften with a brown fur coat, beige scarf and brown shoes
Maybe you feel too casual so you want to add an unexpected gold evening clutch
This category also includes accessories - which I consider the spices of the wardrobe. Do you want something more subtle or do you want something that packs a punch or even purposefully overpowers everything else?
The magic is in how you combine all the ingredients…
Here’s a sampling of some recent outfits that have similar “recipes” and in some cases the same ingredients (see my current black silk scarf obsession) - but I’m able to build something different each day based off what I’m feeling in the moment, my plans for the day, and to be honest what’s not in the laundry.
This took a long time for me to write but honestly it was fun documenting my thought process - hope you enjoyed and would love to hear what you think!
Maybe you’ll choose to make some more thoughtful decisions when getting dressed - or like me pick some inspiration from old school Hollywood actresses (or actors!)
I truly think it’s wonderful that we have the opportunity to choose what we wear every day, and I hope you see it for the privilege that it is and have fun with it!!
xx Caroline
Loved how you worked through the analogy :)
This is a helpful thought exercise! Also love how you make western boots feel accessible