How to make sure you're going to (actually!) wear your clothes
AKA: finding your "personal style sweet spot" -- Part "guide" on how to buy things that you'll actually wear, part receipts of how I wear my clothes
Every once in awhile, I have an urge to organize my camera roll, which includes scrutinizing 1000 pictures of my kids that are virtually identical to determine which of them (if any!) they are all semi-looking at the camera in. It also includes sifting through a gargantuan number of screenshots that I take with ABANDON. Instagram post I want to remember? Screenshot. New Arrival I like? Screenshot. Outfit I admire? Screenshot. Book recommendation? Screenshot. Brand I want to remember? Screenshot. Random piece of information in someone’s instagram story? You get it — a lot of screenshots. I want (and really do try!) to do the iPhone note trick a la
but I lack discipline (and maybe time) to do it all the time, so I have a bunch of half-baked notes and a ton of screenshots.I had a recent urge to lead a more clean and organized digital existence (as I do from time time time), and it led to my scrolling A LOT of screenshots. Screenshots tell a story — You can tell I’m thinking about interiors (working on making some changes to my older two kids bedroom and our primary bedroom and also contemplating a renovation of our own house in a year or two), amateur DIY projects, everyday outfits, bathing suits, jewelry, the best rom coms and thriller novels to gobble up this summer, so many dresses and lots of fun summer outfits. Just to name a few things!
This practice - capturing images, and then, after a little time has passed, reviewing + editing, is one of the best ways to hone in on and understand your taste and personal style — as it relates to everything — not just clothes. As I was sifting through the screenshots, I deleted many, not because I don’t like them (I do!), but because just because I like something, doesn’t mean I’m going to buy it or wear it or try to recreate it. It doesn’t necessarily mean it’s “me.”
It reminded of this piece, which I wrote nearly 2 years ago, about this concept of your personal style “sweet spot” — the intersection of what you love, what you feel great in and what fits into your lifestyle/what you are actually going to wear.
Personal Style Sweet Spot
At it’s most basic level — this explains why you might love something, but it could sit in your closet and be unworn. Or, have many individual things that you like, but stare at your closet with that feeling of, “I have nothing to wear.” Liking something isn’t the litmus test for whether or not it’s your taste, because we like things all the time that we might not want for ourselves. I can think of a number of women whose personal style and outfits I ADORE, but that doesn’t mean that I would want to emulate the same looks myself (or, maybe sometimes I would, but they might make absolutely no sense for my lifestyle!) Maybe home style is an even better example — I love looking at mid-century modern homes and drool over their design, but when it comes to my own home I have a more cosy traditional, english cottage style.
If you want a closet of clothes that you wear (who doesn’t!), you need to be thinking about more than just whether or not you like something (at least, most of the time). You need to ask yourself whether or not it will actually make you feel good (which is about fit at the most surface level, but also about whether or not the style feels good on your body, if you can move in it the way you want to, if you feel comfortable in the item.) And, you need to think about whether or not you’re actually going to wear it.
There should be room for things that you have because you just really love them, or because it brings you joy, or it was just too fabulous to not have, or because it has emotional value. (It is supposed to be fun after all!) And, there are pieces you wear every once in awhile for special occasions (currently searching for a new cocktail dress that I will want to wear a few times a year — high on my list but I haven’t nailed down my pick just yet!) Part of the trick is though, that I have found that USUALLY, if you love something and it makes you feel great — you will find a way to fit actually wear it (once a year counts!)
Actually Wearing Your Clothes
This is especially hard to navigate because we are flooded with people with great clothes and that are also seemingly wearing something new every time they share something. It’s fun to watch and see and be inspired by, but it’s not very relatable! And, no snark when I say this, because it’s a major generalization, but I don’t think it’s a sign of having a great sense of style — anyone with an unlimited budget can buy something fun and trendy and new every time they have an occasion to get dressed. A strong sense of style is buying things that are true to you and mean something and say something about who you are and how you want to be seen when you move through the world. It’s about using the things you have as a way to express yourself, and about collecting things and using them as much as possible.
If you want to actually wear your clothes, then seek inspiration from people who clearly do that. When I think of who does this really well, the first who comes to mind (with a significant following!) is
of The Wardrobe Edit is ALWAYS showing how she wears pieces in her closet multiple ways, and when you see her outfits that she wears on a day-to-day basis, she has a real point of view and consistency. Reva from WEARS her clothes, and is always creating interesting outfits with things that she has worn millions of time. Another is Mary Hafner who I have followed on instagram for years (as far as I know she’s not on Substack!) also has (what I imagine is) an INCREDIBLE collection of clothing, but also — she repeats things, wears pieces in a variety of different ways and has a real point of view in the way that she dresses. Elyse Winter is a stylist who has an incredibly distinct POV that translates into the most wearable outfit ideas from herself and her clients. I screenshot A LOT.Substack is one of the best places to be able to find more women who are just sharing what they’re wearing — to normal lives, as moms, or not as moms, as professionals, or self-employed, out on dates, out with friends, running errands, just because. A quick spin through my homepage and I am inspired by
(I am forgetting gals I shouldn’t be forgetting, please forgive me!)… I could go on and on about this (would love to know more suggestions of people I should be following/subscribing to!!)I love new stuff, just like anyone else, but I also want a closet of clothes that are lived in. In the past several years (honestly, in many ways, since I became a mom 7 years ago, and at first felt completely unlike myself, but then eventually found myself more confidently than ever) — I have shifted from wanting to wear something new every time I have an occasion to wanting to wear things I love all the time (and, sometimes they are new!) (I also don’t have an unlimited budget…maybe someday!). Part of why I write and share in this newsletter is because I want there to be more examples of real women who actually wear their clothes a lot. The concept of “the personal style sweet spot” has helped me be better at buying things I’ll actually wear without having an intense system or “rules.” I’m more of a guiding principles gal. The proof — in the past several years, most of the pieces I’ve added to my closet have been (mostly) the types of things that I reach for and wear on a regular basis.
My Receipts
A black linen (or any color!) pant is something I wear to work, on casual weekend stuff with my family, to the pool, and to a party. While not a particularly revolutionary style — these fit me very well, have an elastic waistband that doesn’t get tangled, a true straight leg (a requirement for me) and are not too long as to look sloppy (so I can wear them to work) and with a variety of shoe options.
Since many of my days are spent in an office, getting dressed for work is a huge part of what I get dressed for over the course of a week, month, season, etc. I often measure things based on whether I will be able to wear them into the office (in addition to other occasions), but — not always! This exercise dress is a great example of something that has become a bit of a weekly uniform for me. I don’t have to think, I can reach for it, feel put together, have a few different ways to style it, and am comfortable and not hot!
Okay, one last one, this time going deep into the archives. I bought this oversized denim shirt in 2023 as SOMETHING to have that would fit me when I was pregnant with my third. It’s the perfect layering piece, that I go to time and time again — especially in season transitions because its the perfect extra thing to have in case it gets a little chilly. Gap doesn’t appear to be making this anymore, but some really great similar options: from Faherty, from Sezane, from Agolde
Doing this at home
In addition to using the “personal style sweet spot” framework, there are a few specific things help me consider something new:
Trying the piece on at home with other clothes I already have, and trying to make at least 3 outfits (AT LEAST)! And ideally outfits that I would wear to a few different types of things I get dressed for.
Taking the FULL RETURN WINDOW to think about a purchase. I do advise understanding exactly what that return window is ahead of time and putting a little reminder the day or two before you have to mail something back so you don’t forget! If I love something when I try it on (if I don’t love it, I try really really really hard to immediately return, because it is almost always a sign that I don’t really like it or it doesn’t fit, and should not stay), I will take a few days to try it on a few times, with different pieces, to make sure I like it.
Consider whether I can wear it with my favorite “x” — So, if you’re considering a shirt, can you wear it with your favorite pair of jeans? Your favorite trousers? Your favorite skirt? If you’re considering a pair of flowy pants — can you wear it with your favorite t-shirt, your favorite tank top? Your favorite flats or sandals? Your favorite belt? You don’t have to say yes to all of these, but multiple “yess” is hopefully a sign that this is a piece that you could get a lot of wear and inspiration from. A nice little bonus is that doing this (and taking a picture of the outfit that you put together!) helps you build a little arsenal of outfits that you can wear when you don’t know what to wear!
Let’s try this exercise with something I have had on my wishlist for awhile — it’s this top + pants from Faithfull (one of my favorite brands). I LOVE a matching set, but have learned that I need to be picky specific about them because while I LOVE A PATTERN, I’m not a huge pattern wearer (more specifically — I’m not a huge re-wearer of patterns). I also don’t need anymore flow/oversized/button down shirt with matching flowy pants types of pieces - not that they aren’t amazing, I just have plenty in my closet, so adding isn’t actually filling a gap or making getting dressed any easier.
So — my criteria for a matching set:
Structured top (not flowy)
Solid color (that will work with other colors I have in my closet)
Can be dressed up or down
Here’s how I thought about this ahead of time to think about how this fits into my wardrobe (I’ve ordered but it hasn’t come yet, so stay tuned!). This is in addition to wearing it as a matching set what I will obviously do if I keep it!
I wanted to think about how I would wear this to a variety of different “types” of things to get dressed for — including nights out, work-events, casual family things, and the office. The top, because of it’s structure will pair nicely with slip or knit midi skirts and flowy linen pants, and as it starts to get cooler, I can wear it as a going-out-look on the weekends. For a more casual look, I know I’ll pair the pants with a simple boxy tee, but I can also pair with a knit tee and ballet flats for the office. The pants are also office-friendly with a crisp button down or structured vest (I particularly LOVE red and brown!). If it fits, and I feel great in the set, I think it passes all the tests!
When you shop in person (although amazing in many other ways!) you (obviously) can’t try on a potential new piece in real-time, so I like to consider:
None of this is by any means rocket science, but it is something that has really helped me think a little smarter without being too intense about it, and also remind myself that just because I love something, that doesn’t necessarily mean I want it or that it belongs on my wishlist (or that I should buy it!) At the end of the day, we all want to feel good, like ourselves, and reduce the amount of times we stand in front of our (full) closets feeling like we have nothing to wear. At the very least — a reminder that wearing your clothes over and over again, and re-wearing pieces and outfits and full looks is AMAZING (and normal!).
Thank you so much for reading — that’s all for today. I hope you are having a great August, and soaking up the last however many days of a true summer vacation that you have. We don’t start school until right before labor day, so, even though I have a little bit of that “summer is over” panicky feeling, we actually have a lot of time to go! Hit the beach. Have a beer. Wear something fun. Lots of love.
PS: find all the pieces featured in this post here.
ICYMI
From the Archives: To All the Vacations I’d Love to Go On
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I love these questions! I feel like finding my post partum style vibe has been a lot of “what is the life that I’m dressing for/shopping for”…I love the idea of making 3 outfits with what you have!!
SUCH a helpful post and thank you for the shoutout Christina - that is truly the best compliment! x