STARTING FROM SCRATCH
With my denim. (Not by choice).
In case I haven’t mentioned it enough… I had a baby in June. I mention it a lot because it is kind of a big deal in my life. And while I don’t expect the birth of my son to have quite the same impact on you as it did on me, I will say that these past seven months have had a profound impact on my skills as a stylist, a wardrobe therapist, and a content creator. So in a way… it actually does impact you as a reader of this newsletter or a potential client. So….. stay with me. Get invested. This is going to pay off for you!
Luckily, it has changed me for the better and taught me a lot about understanding fit and proportion in a different way. When I was a stylist (and a stylist assistant!) working in the industry in a more Fashion-with-a-capital-F capacity, I thought that I was really good at “styling all kinds of bodies!” I am not sure why I thought that exactly, because in my glory days (from 2008 to 2018-ish), I was actually not even exposed to “all kinds of bodies!” I worked mostly in editorial and celebrity styling, and there was only one kind of body to be styled. And you know which kind!
In 2019, when I started taking on wardrobe styling clients, I realized that I had a lot to learn. And I was so lucky that I had so many clients to teach me. What I learned is that, as women, we know our bodies really well. Like…. really well. On the surface, that is a really good thing. We are aware, we are attuned, we are perceptive. What isn’t such a good thing is that most of us women weren’t really raised to like ourselves very much. In fact, a lot of us walk around with a full-on war going on inside our heads. So this knowledge of our bodies is often just used as a tool to criticize ourselves, limit what we “can” wear, and keep us small and insecure. My clients have told me all kinds of things about their bodies in our styling sessions—I have high hips, a short torso, broad shoulders, a thin neck, ugly knees, chubby ankles! And through listening, observing, and walking through many wardrobes, I think I now have a pretty good sense of “styling all kinds of bodies!”
And the one body that I was really good at styling was my own! I have had it for a while! I know it. I wouldn’t say I love it, but I think I had a decent relationship with it. I can walk into a store and know what will work. I can see a pair of jeans online and know if they are worth trying. I usually have a handle on what size I will be based on the measurements. But that has all changed. After giving birth and allowing my body to reconfigure, all bets are off. I am now looking at a body that feels foreign, and I am figuring out what works. And as a “jeans and a t-shirt” gal, the most destabilizing category for me has been denim. I am in a place where the jeans from pre-pregnancy technically fit, but they fit different. And they look different. And I look different. And I look at myself different.
I don’t think that I had to go through a transition in order to relate to my clients on a deeper level, but it didn’t hurt. I can now really say that if you also feel lost, I have stood where you are standing, and we can figure this out!
I figured that I would approach this personal transition the way I would approach it with a client. So here is my process for SLOWLY rebuilding a denim collection.
After any big transition, I think a closet evaluation should follow. There is a beauty in allowing one change to facilitate another, and when we go through something monumental, our style often experiences a shift as well. What we wear is a reflection of our interior life, so it makes sense that our wardrobes will want to catch up with our evolving self. If you are interested in where I started pre-pregnancy, I actually filmed a denim try-on HERE. (Side note: when I filmed this, I remember feeling insecure, but now I look back and think I look so cute and good. Perspective!)
During my pregnancy, I threw all of my denim in big plastic bins and stored them in a different space than my current closet. When I began to fit back into things, I opened the box and began to try things on. I envisioned this being a slower, more meditative process, but the reality is that it was kind of intuitive. I hardly even needed a mirror. I would put a pair on, and I could tell immediately if it was a yes or no. The feeling was very important. And I don’t necessarily mean comfort. I mean when you put something on your body, you immediately know whether it works or not. I think when we need to hem or haw, we are actually often trying to talk ourselves in or out of what our gut is telling us. Even though I felt a bit unstable in my body, I still have that intuition of what feels right to me. And weirdly, some of my former favorite pairs were an immediate no. A few took a few spins for me to let them go. For example, I had a pair of unisex Balenciaga jeans that my friend had tailored and gave to me, and they were my most worn denim of 2024. I kept trying to style them postpartum, and the proportions were just so off. They were tight in the wrong place, and even the color somehow felt wrong all of a sudden. So after wearing them to work a few times and feeling a bit off, I realized it was time to part with them.
My process for trying on my denim was exactly what I would tell my clients to do… start with the best. The first pair you try on should be the gold standard. Then you move down the line. If something does not measure up to the favorite pair—it should go. After all, if you have a pair that fits amazing and you love, why would you wear a pair that fits worse and you don’t like as much?
I will typically do this by category. In my own wardrobe, I am a big white jean wearer. So I started first with my favorite white denim, which are The Row Eglitta. I know they are insanely expensive, and I don’t know what to tell you about that. But they work for me. I ended up purging all of my other white jeans because when it comes down to it, if I am wearing a white jean, I will grab the ones that look the best on me (edit—I realized I also kept my Phoebe Philo Drop Jeans in white, but those feel more like trousers somehow?). I did this with straight-leg jeans, wide-leg jeans, and found that I was only left with 4 pairs!!!! And I actually think this is a fine and manageable number for me, to be honest.
I don’t think that I (or you!) need to have a checklist of different styles and washes. I don’t think EVERYONE needs a straight-leg jean. And I don’t think we all need a pair of black denim. With denim especially, I think we make the biggest mistakes when we are trying to check a box or satisfy an arbitrary category. After looking at the 4 jeans I had left, I didn’t feel like I needed to get a dark denim, for example. In evaluating what I kept, I actually realized that the best way to figure out what I needed is to take it slow. I lived with these 4 for a while, and if I was styling something and felt like I needed a different denim silhouette, I made a mental note. I didn’t immediately purchase it. What I came up with is that I wanted an easy bootcut or flare that was slouchy to throw on with a more fitted t-shirt. I was left with wide jeans and a slim pair and was craving something in between. But I could have only deciphered that by really living with these for a bit!
With jeans (I think more than any other category), we are always leveling up. I don’t think any woman will ever be satisfied with the jeans that she has. If she loves a high-rise straight-leg jean and has an amazing pair, she will still be looking for an even more amazing pair. This is just the reality of denim. So I think it is a hard-working but kind of transient category. If you have a pair that you love but you find a pair that fits better, then fine, get the one that fits better—but you should absolutely edit the one you are replacing. In my opinion, this is where we get in trouble. We will get a leveled-up pair of denim but keep the worse version, and then we end up with piles of similar jeans.
I know I said 4 was manageable but I am a crazy person and a stylist and I got some more over the past 8-ish months. Here are the jeans that I have added to the rotation and why!!!!
WHY: I became aware of this brand while I was pregnant and was SO excited to try them. I am always really intrigued by a new fancy denim brand, and I was desperate to try. Since I found myself wearing my Phoebe Philo khaki-colored jeans so much, I thought it might be overkill to do brown, but something about the color and texture really spoke to me. I took my normal size and am so happy about it. They slouch down enough but don’t feel too baggy.
And I am going to tell you something. Lean in close. If you want to get a fancy pair of denim… don’t bother with Khaite jeans (I love the brand, but not the jeans, sorry!). I actually really don’t like them—they have a tough fit. If you have money to burn on jeans, I would go for a pair of OSSOU or RUADH! They are pricey, but they feel expensive!!!! The Ruadh jeans feel like a designer jean, and both brands have pretty buttons like Khaite.
HOW I STYLE THEM:
WHY: I am always in the market for jeans that are low- or mid-rise and a bootcut or flare. So these were kind of a no-brainer for me. I used to only wear jeans in this mid or light blue color, but I noticed when I was taking inventory that I am being drawn more to brown, black, and white. However, when I tried these on and got them home, I found myself grabbing them every day.
I went a size up in these jeans, but I wish I didn’t, honestly. They have enough room in the leg, but they are a little too big in the waist now. I should have returned them for smaller, but I am still wearing them a LOT. I have actually learned that I like to wear jeans a little bigger.
I think it is also interesting to note—when you ask influencers or Substackers what size they wear, there is a lot to consider beyond the number, so take it with a grain. I think we often forget that people have different preferences, and someone’s “size” is not a fixed number. I own denim in various sizes depending on how I want them to fit. I put myself in the driver’s seat when it comes to sizing. Of course, I know what number I typically try, but that does not necessarily make it “my size.” I take whatever size works for me in a particular style, fit, wash! More on that below!
HOW I STYLE THEM:
WHY: I was really excited to finally get the Lenny experience. If you are not familiar, Love Lenny is a store in LA where you try on a bunch of Levi’s, and the amazing team customizes them to your body and preferences. You can do virtual as well, but I think it is a really fun experience to do if you are in LA. Before your appointment, you fill out a questionnaire of what you are looking for, and they pull some pieces for you, but as we were trying on, we got a sense for sizing and what worked.
I tried on about 20 pairs of jeans (maybe more!) and ended up loving the Levi’s 517 and also liked a low-rise Levi’s Silver Tab, but ended up going with the 517. In doing this, I realized that a denim non-negotiable for me is comfort. Who knew?! I didn’t really think I cared about comfort, to be honest, but as we were trying, it became clear that if I had to work even a little to button them up… they were a no.
A few times, Lenny saw me abandoning pairs before fully getting them buttoned, and she said, “You can get those buttoned if you try, you know!” And I buttoned them up and will admit… they looked great and snatched my waist, but I realized that isn’t actually what I am looking for in denim anymore! There was one pair that I was close to getting that were super fitted in the waist and actually gave me a good butt, but I was very real with myself and knew I would never reach for them. Maybe someday (never say never), but not right now.
I was VERY happy with the 517 and am excited for them to arrive (they pin them on you and then tailor them, then ship them to you once they are ready!). PS: this is not sponsored—I paid full price for the session and jeans! I just really enjoyed the experience!
HOW I STYLE THEM:
WHY: I am a Phoebe Philo jean–obsessed person. I tried my first pair at Bergdorf when they had the first collection, and I became obsessed. I always wanted to get the slouchy look, but I could never seem to nail it, and the Phoebe Philo jeans feel like they have the slouch I am looking for. They have a really long rise but are meant to sit at the hip (as a low-rise lover, this works for me!), so they have the baggy look without feeling like the low-rise jeans from my high school days. They are also very long, which I enjoy. I was going to get this particular pair tailored, but I have just been cuffing the hem, and I like the look.
These were probably not necessary to add to the collection, but I have worn them a LOT. The Phoebe Philo jeans are also soft and a bit more drapey than they look, so these are really easy to throw on to work from home.
HOW I STYLE THEM:
SPECIAL MENTION: Honestly, these are technically denim, but I wear them almost more like sweatpants because they are so soft and slouchy and comfortable. I took my normal size, and they have the right amount of slouch for me. I usually throw these on with a T-shirt, a crewneck sweater, and flats and wear them to work from home or on the weekend. They are so perfect if you want something that looks intentional and cool but is still comfortable and easy to wear/wash!
Denim is the trickiest category, and I would say 7/10 clients have “denim” on their list for links that they want me to send. There are so many options, sizing is psychotic, and there is so much discourse around what is “in” and “out” these days. Here are a few tips to keep in mind when you are shopping for denim:
BE SIZE AGNOSTIC: Like I said above, you are in the driver’s seat here. Try multiple sizes and compare and contrast. Some things look better baggy, some you want more fitted. The only way to know what you prefer is to try. When I try on jeans, I typically take the size I think I am, as well as a size bigger and a size smaller. It is great to be able to compare and contrast and see what is comfortable!
TEST DRIVE: I have had so many clients show me jeans that they are hoping will “stretch out”—if something feels a bit tight in the dressing room or when you try it, I would try a size up just to compare. Some jeans stretch, but too tight is just too tight. I usually walk around, sit down, and take a second in the jeans before I commit.
TAILOR: It is crazy to expect jeans to fit us perfectly off the rack, and a lot of people who have amazing jeans have had them tailored. Hemming the length is super easy, but you can also nip in the waist a bit, too. I would take them to a tailor to understand what will be required before taking off the tags!
BE STRATEGIC: I mentioned this above, but it’s worth repeating. Do not look at your denim wardrobe as a checklist. There is not a prescribed inventory that we all need. Think about what shoes you wear, what top silhouettes you gravitate toward—that will help you figure out what jeans will be most useful.
DON’T GO OVERBOARD: I often get really excited when I find a pair that I like, and I want to get them in every color (and sometimes I do! As you see with the zip jeans!!), but I find that when I get multiple colors, I usually end up liking the original one the best. First of all, the reason we like the original also has to do with the color. When we try to replicate it and get it in another color, it often ends up being less easy, or even worse, it yields the same outcome. When I am thinking about my denim assortment, I want them all to do something different and create a different outcome for the look.
Second, I think we are always upgrading our denim. Denim trends change all the time as well, so I think fully committing to one style is pointless. You won’t want to wear them forever, and chances are by the time you need a new pair, you will be sick of them. You know I am very into the idea of investing and buying things to keep forever, but with denim, that feels like a fool’s errand!
Just a last little note—I have seen a lot of people taking the opposite stance on fashion recently, saying that “it’s not that serious” or “who cares,” but rich, poor, old, young… getting dressed can be a siphon for all of our clogged-up emotional anxiety! When we can’t find the right thing to wear, all of our anxiety, vulnerability, and frustration comes out. I think it does matter, and it is that serious!!!!!
And if you are interested in my journey to become hotter, I will be giving a progress report for the paid tier! Be sure to subscribe and upgrade if you want to get two newsletters a month!!!!
As someone who went through postpartum twice I would just recommend you to hold on to some of those old favorite pairs as the body tends to shift for up to 2y after pregnancy. Loved the post! x
I have so much enjoyed your posts on learning to re-dress and re-style after pregnancy. I'm a fellow jeans a t-shirt girl too. There is so little out there on this topic with *taste*, precision, and delicacy because every situation is different. And honestly I don't want to look like a peasant princess in a tiered dress (personally). I am pregnant and reading these to prepare for yet another bodily change (happy for baby! just dreading the pp outfits). I so appreciate this!