Before you buy, ask “why”

and a few other things, too

and a few other things, too

It will come as no surprise to anyone who knows me that I’m not a minimalist. Stop laughing. I am not going to have a uniform. I am not going to create a capsule wardrobe. Instead, I am constantly curating my closet to represent how I feel on the inside which is constantly—thankfully — evolving.

That said, all appearances to the contrary, I am very particular about how I shop. It’s true that I have a lot. It’s true that I don’t give myself a specific budget. But I am strongly against waste. And while shopping without regrets is pretty impossible for a non-minimalist, I’ve gotten to a place where I shop far more conscientiously than ever before.

Part of that is weaning myself off fast fashion completely. It hasn’t been easy. I love Trinny Woodall (what, you’ve heard?) and I totally understand why she uses fast fashion pieces to reflect her point of view in a way that is accessible to all. Seeing how fantastic she looks in things from Zara makes them incredibly tempting. But I resist. Because what I’ve found is that ultimately I am never satisfied by these items. And it when it comes time to get rid of them, it’s harder than it is with a more designer mistake. I find more long-term satisfaction if I buy designer used, and that’s easier and easier to do with so many designer resale options like The Real Real, Decades, and Tokio 7.

So for example, when I watch Trinny, I think about how to replicate her perspective (layering, shimmer, color pairings. etc.) with used pieces from my local consignment shop, or the Real Real or eBay.

Another thing that helps me is to ask myself a series of questions before I pull the trigger on a purchase.

Here are those questions in case they help you too.

1. Is this an upgrade of something I already own and use and love? If so, then I’m more inclined to buy it because I know it will work and make me feel even better than the original. Then the question becomes: Am I willing to sell or donate three or more of something similar? For example when I saw these funky, creamy Margiela flat sandals and wanted to buy them I thought about their function in my wardrobe: neutral, warm weather, covers a lot of foot shoe. I had all these pale peekaboo heel sandals and mules that I wasn’t wearing because they didn’t reflect how my life had evolved (less workwear, more walking, feel cooler in a flat). I got the sandals and also sold four pairs of shoes I wasn’t wearing. Seeing these helped me determine what wasn’t working.

These felt so fresh + new and “me now”

Said bye to these + 3 others

2. Is it an answer, or does it raise more questions? I have enough things to do that I don’t buy something where I’ll need to do this and do that. Like does it require a shoe I don’t have? Will it show my bra in a not-ok way? Will it only work with tights? What will I put under, over? How do I get it on exactly? Things like that. No. Too hard.

3. Will this item make a bunch of my existing pieces that I like instantly wearable? It’s why I got a men’s croc belt from The Real Real recently. It’s a thing that can take an outfit of all navy blue or all various shades of black and give it that little kick that turns it into something and I have a lot of outfits like this. It’s an answer.

This men’s croc belt makes my black skirt and so many other things feel easier and more interesting.

4. Is it eased out in the way it looks/feels? Is it easy is one thing. Easy to deal with. Easy to fit in with what I already have. Another thing is: Is it eased out. Meaning, is it tricky? Are there sort of tricky details, a fake shirt layer, lacing up, stuff like that. Is it going to be tight? Pencil skirts, super-fitted waists — that’s not eased and I’m not interested. Fussy, formal, effortful. (Is that a word?) No.

5. Am I drawn in because of nostalgia? Nostalgia is a very powerful thing. It kicks up this emotional impact of a time that in some way or another we’re wistful about. It’s what makes me sometimes drawn to preppy loafers, take offs on rugbys, anything Thom Browne. I’m reminded of summer nights after high school graduation, flirting with a friend’s older brother, sparks from a beach bonfire. While it’s fun to look back, I’m happier now. Still, sometimes I’m vulnerable to the “wham” of a feel-good memory and the associated item takes on a mistaken (but strong) appeal. I like to look and feel modern, though, so it’s best to take a breath and remember this old me without now dressing like her.

I tried on these Vuitton loafers that made me think of the Bass Weejuns a friend gave me in high school that I called my “super shoes!” I did not buy.

6. Am I doubling down? This is what I just recently discovered, and it’s really weird. Sometimes when I make a mistake, I might double down on something similar. WTF? I think it’s tied to not quite wanting to admit it’s a mistake even to myself or feeling slightly that it’s a mistake and wondering if I can do it better. Or not wanting to part with something because it once was so me and parting with that item might admit that I am changing so instead I try to upgrade that piece or get another something to make it work when in reality it’s time to move on.

7. Is this my style or is it someone else’s great style? If fashion (according to Amy, and I agree) is about finding a match between the way you feel inside and the things you put on your outside, it’s really important that everything you buy first and foremost be on brand for you. Sure there are exceptions; Amy talks about being drawn to white embroidered Chanel and I can see that, and then you style it in a way that’s you. But I don’t want to fall into the trap of looking at something and thinking “because it’s beautiful I want to possess it.” It might be beautiful and I can just say wow that’s beautiful and move on. Kind of like when Barack Obama was president and you’d see him and say, flickeringly, oh my. But you didn’t become, like a president-stalker. You continued making coffee. When I see something beautiful that’s Chloe and bohemian, I can say oh that’s beautiful for someone but that someone is not me. It’s Michelle. Also: My husband is sooooo cute.

8. Do I want to wear this tomorrow? Sure, there are things that I put away for a while and then fall back in love with but I think for the most part the best pieces you want to wear immediately and the CPW immediately starts dropping.

9. And even better yet, could I decide tomorrow? This one works in two ways. First of all, it tells you how much urgency you really feel about the piece. If you’re willing to risk it selling out, maybe you just don’t need it. And second it just gives you a little breathing room if you’re caught up in the emotions of it all. It’s good to breathe.