The Easiest Way to Pick the Right (or Wrong) Shoe
The grid that works with every outfit, every time
Hallelujah—finally a series where I actually write two consecutive posts on the same topic.
Here’s shoes, part dos that answers what shoe, when?
In Part 1, we went over a framework for evaluating your shoe closet.
If you haven’t read that yet, start there — I reference those concepts throughout this post, and otherwise you’re going to be like “???” the whole time.
If you did read part 1, I have GREAT news. As long as you understand those concepts, the rest is easy! No new 2x2s to master.
Alright, ready? Let’s jump in.
When I asked folks in my Substack chat their biggest shoe dilemmas, they mostly boiled down to two buckets:
How to pick a shoe when you’re starting from the clothes.
How to build an outfit when you have to start with the shoe — e.g., days when only a specific comfortable pair will work, and then work your way up.
We’ll take these one at a time.
Today is about the first one: starting from the outfit.
People often ask, “Which shoe should I wear with this outfit?”
The truth: almost any shoe will “go” with almost any outfit. The better question is:
What’s your personality? Do you like harmonious outfits, or do you prefer friction?
What are your style words? How do you usually like to feel in your outfits?
And perhaps most importantly, how do you want to feel today?
I make “getting ready” reels on Instagram where I pick one of two shoe options for my outfit. Sometimes, when I watch them later, I wish I’d picked the other one. That doesn’t mean I was wrong then or wrong now, it just means I felt differently in that moment.
So if almost any shoe works, how do you pick the one for today?
Enter: the 2×2 grid from part 1.
Step 1: Place your outfit on the 2×2
The grid has casual ↔ polished on one axis and slim ↔ big on the other.
Example: a white graphic tee and classic-wash jeans = fairly casual, and somewhere in the middle of slim ↔ big.
Step 2: Decide: Double Down or Create Friction
Once you know where your outfit sits, ask yourself if you want to double down on the current vibe of the fit, or if you want friction.
Double down: Pick shoes close to your outfit’s position on the 2×2 → reinforces the vibe.
Friction: Pick shoes further away on the 2×2 → adds a second, contrasting vibe.
Think of it like this:
Casual shoes with a casual outfit = even more casual.
Polished shoes with a casual outfit = friction — two different moods coexisting. This adds nuance, and it’s basically the “wrong shoe theory1”: choose something that lives far from your outfit on the 2×2.
And no, I don’t expect you to do this every morning
Do I expect you to pull out a graph and plot your outfit daily? Absolutely not.
This is a learn it once, use it forever kind of thing.
Think of the 2×2 like training wheels for your shoe brain. The first time you do it, literally draw it, place your outfit, and then try one “close” shoe and one “far” shoe. You’ll feel how much the vibe shifts. Once you’ve done that a couple of times, you won’t need to draw it again.
Instead, you’ll just see where an outfit lands in your head and instinctively know whether you’re in the mood to double down or create friction.
I don’t want to make you overthink every outfit. It’s to give you a mental shortcut so you stop second-guessing and start picking shoes that make sense for how you want to feel that day.
With that, let’s go into some examples:
Example 1: White Tee + Jeans
Alright, let’s look at a range of outfits:
Example 2: Orange Silk T-Shirt Dress
This dress is a tricky one. It is a little bit casual, a little bit polished, it’s big, but it drapes in ways that makes it look slim. Honestly, don’t overthink it and just go with your instincts of how you would think about an item that can be in-between. This is all subjective and a way for us to make decisions and sharpen our intuition, not a perfect science.
Do you see it play out in the fits?
Example 3: Tropical Wool Shirt + Trouser Skirt
And now a more polished fit, a wool buttondown shirt with a trouser skirt. Here’s where I would place it:
Also, I couldn’t find my taupe sneakers so I put on blue sneakers for the example. We will come to color next, but for now pretend these were taupe.
Colors
How do you layer color? A reminder of the color cheat sheet:
Black → Adds edge
White → Adds crispness and clarity
Brown → Grounds the outfit, softens things
Metallics → Add glam if brighter metallics, and glam+breezy calm if champagne-y
Brights (ring 4) → Inject energy and playfulness
Muddy colors (ring 3) → Very similar to brown, will usually add grounding
Nudes → Disappear or elongate
Why color comes last(ish): Shape and polish set the mood first. Color tweaks it.
Let’s go back to our jeans + t-shirt example.
If you decide “I want a black shoe” but the only black shoe you own is a sandal, you’ve automatically locked yourself into a casual-casual mood.
The exception: If you have a large, versatile shoe closet, you can start with color first.
When you can say “I want a blue shoe” and choose between a blue sandal, a blue pump, a big fluffy blue mule, or a chunky blue boot — you can still pick your mood after choosing color.
The connection to building your shoe closet
If most of your outfits are big and casual, and you’re feeling “meh” about your shoes, it might be because they’re all the same vibe. Add a little friction — a slim sandal, a chunky boot, or even a polished slim loafer — and suddenly you have friction tools.
So how do you pick the ‘right’ shoe
Much like part 1, this one isn’t giving you ONE PERFECT ANSWER! See, that’s not how style works. My objective in my writing here is to share tools that help you sharpen your intuition. In this case, I am hoping this gives you insight based on how you want to feel that day.
Friction outfits stand out and feel more directional.
Double-down outfits feel harmonious
Make the call: Do you want to blend in or stand out today?
Next time you’re standing in front of your shoe rack, maybe try both — the “close” shoe and the “far” shoe — and see which one feels like you right now.
You might be surprised which one wins.
PS: No affiliate links here. If you are curious about something, just ask in the comments. If you are into this post, the best way to support me is by liking the post, commenting, and sharing it with your friends. I super appreciate it!
Another amazing post, Asta! So helpful. Overlaying the outfits on the grid is genius!
Brilliant!!! This is such a good system, especially for someone like me (visual learner here 🙋♀️)