Issue 104: The three-outfit test
Buy the thing. Then do this
Summer’s in full swing in Toronto.
This is what I put on during the heat wave last week: donni linen shorts, a redone tee from last year, black flats (the pair I cut the bow off), my thistles sunglasses, and my new black top handle bag. Partly because it’s too hot to wear something on my shoulder, but mostly because I love the contrast it adds to an outfit like this. (I convinced a client to buy the bag and then immediately convinced myself. Occupational hazard)
As of tomorrow, I will be “out of office” for the week (air quotes because when you work for yourself there is no such thing and my office is my phone).
August is almost full and September has already started filling up, so if you’ve been thinking about booking a session, you can do that here.
One thing that’s come up again and again recently with clients is overthinking.
Not just about the big decisions. About the small ones too. A tee. A shoe. A bag. Something that’s $800. Something that’s $80.
A client will hold up a piece she just bought and ask me:
“Do you like this?”
“Do I need this?”
“Do you think it’s the perfect summer top?”
These are the wrong questions.
Do you like it?
And, more importantly…what are you going to wear it with?
Here’s the thing. Some of my best purchases have been impulse buys, and I don’t regret a single one.
You don’t always need a strategic reason to buy something you like.
There is no perfect jean. No perfect tee. No perfect anything.
There are only pieces that work for you, your taste, and the momentum of your life right now.
You just need to wear it.
Which brings me to the only rule I follow without exception…
The three-outfit test.
Whatever you buy, style it with three outfits before you decide if it stays.
Not three outfits you could theoretically wear.
Three outfits you actually try on.
Three outfits you look in the mirror and like.
Three outfits you would genuinely wear.
If you love all three, the piece is a win. If you’re forcing it, you already have your answer.
Was it a splurge you didn’t need? Overpriced? Not filling some strategic gap in your closet?
It does not matter.
You just need to wear it.
If you buy something without thinking about how you’re going to wear it, you’re setting yourself up for shopping mistakes.
That’s how you end up with a closet full of clothes with the tags still on them.
The test is simple:
Does this piece help you get dressed in a way that feels like you?
One of my purchases recently is the perfect example. A red tank I absolutely did not need. But the three-outfit test gave me the confidence to keep it.
