issue #72: lessons for dressing the life I have

rather than the life I want, even though they're nearly the same thing

First, let’s start with what I would want in life that I don’t have now, so we can get that out of the way:

1. A brownstone

2. My own shop

3. A flexible schedule

4. Hours to spend writing in coffee shops

5. Quarterly trips to Paris

6. A published novel

7. Enough financial security that I never have to think about it again

Despite not having those things, my life is actually not so bad! I have a beautiful, perfect daughter, a loving husband, regular paychecks, food on the table, and a roof over my head. We live in our dream neighborhood, I get to shop with someone else’s money for a living, and I spend time in community both irl and online through yoga teaching and Substack, respectively. I’m healthy, able-bodied, and although sometimes have bouts with depression and anxiety (what millennial doesn’t, let’s be honest), I’m fine. It could be, and frankly has been, worse!**

But as part of this publication? blog? whatever it is, I spent a couple weeks earlier this year documenting my life by day, including what I was wearing. I’m in the process of a low buy year (I have too much stuff!), but through noting what I was wearing each day I realized I actually do have some holes in my wardrobe that need to be filled. Ok, not need, but that I would like to fill. Things I kept wishing I had when I got up to get dressed in the morning, or things that it feels time to replace.

As my life has changed - hi baby and new job - so has both my style and the brain space I can allow for getting dressed. Not drastically, by any means, but as I’ve grown from selling specific brands to working with many in my day job, and as I’ve turned some of my personal time to focus on shopping and style here, I’ve noticed that I am getting better at figuring out who I am, what I want to wear, and what my actual personal style is. There’s been a lot of “intuitive style” chatter floating around Substack lately (cc:

Maureen Welton

) and that’s a bit what this journey is feeling like to me. How to get into a space that feels more intuitive than prescribed, more personal than trendy, more aligned with my lifestyle than pretending I’m living a life I don’t have (although I do think that’s ok sometimes too…dress for the job you want, you know?)

Lesson #1: my life is dirty and requires a lot of walking

Guys toddlers are really, really messy. Or maybe just ours is, but I’m pretty sure it’s all of them. If I get dressed before she’s done eating breakfast I can almost guarantee I will need to change either my shirt or pants (or both) before I leave the house. So this isn’t really a style lesson as much as it’s a personal realization that I am structuring my mornings all wrong. Also that I need to lean heavy into a machine washable and durable wardrobe.

Which brings me to that second point - I walk a lot. I mean, it’s New York City, so that’s kind of a given. But it also means practical and comfortable shoes are a must, and layers are key.

Lesson #2: my time is limited, simplicity is better

I wake up, usually, around 5:30 am. I have sanity-keeping alone time from then until about 7, when my daughter wakes up. If I have to drop her at the nanny I need to be at least showered by 7, if not fully ready (save for being dressed, see above). She has to be at our nanny by 8, so that leaves just about 45 minutes in the morning to get myself ready, get her ready and fed, and get out of the house. It’s chaos! That chaos means I need to either plan my outfits in advance or keep them simple. I have always been a fan of uniform dressing, but now it feels almost necessary for my life.

That said, I do still have a deep desire to look put together, well-dressed, and like a real human multi faceted person in the world, not just one that’s been reduced to “mother” - a label somehow both admired and condescending in our society these days - and thus I should dress accordingly. Not that mothers aren’t real human multi faceted people in this world, because they very much are, but if you’re reading this, I think you know what I mean.

one of many nanny drop offs, a baseball cap always makes me feel a little more put together, for some reason

Lesson #3: my body has changed

Listen, I know my body did amazing things growing and birthing and feeding a baby, but the transition from my “old” body to my “new” body has not been smooth or easy for me. I realize that it’s a little taboo to say you miss your pre-baby body, that we’re supposed to be proud of everything it’s done, that we’re supposed to care more about the crying bundle of joy that came out of it than the vessel that bundle was carried in for those nine months…but I miss my body!! I’m sorry, I do!!! There’s this one picture that haunts me from my youth and it’s me and some girlfriends around the pool at The James and it was before we all got married and had babies and entered our 30’s and we were making questionable life decisions but we all had flat abs and nice tans and honestly we look fucking hot and I know I likely won’t ever look like that again and that makes me a little sad!! I miss that hot bod of mine!!

But, I also realize that something that will help me feel better in this “new” body is dressing for it. Not trying to pretend I have my body of yore, but actually leaning into the sizes that fit me now in the silhouettes that suit me now. And maybe eventually it will shift and change again and I’ll have to shift and change my sizes and styles again and that’s ok. But for now, time to part with the unflattering relics of my past and invest in the things that make me feel good.

Lesson #4: I am a creature of habit

I wake at the same time every day. I eat the same lunch every day. If I didn’t have others to feed with me, I would eat the same dinner every day. I wear a variation of the same clothes every day, listen to the same podcasts and music every day, and rewatch the same shows over and over. I am nothing if not consistent and I find that being a creature of habit allows me the brain space to focus on mothering, taking care of myself, my work, my side job, and my passion project. So it’s fine! But as with lesson 2, this just means I’m giving myself permission to find a few key items that really work, buy in multiples, and wear a variation of the same thing each day.

Lesson #5: it’s ok to invest on occasion

I am on the cheap side when it comes to buying clothes, I’ll admit it. I hate spending a lot, even if I know the value and expect a decent cost per wear. Perhaps it’s because I made some poor financial decisions in my 20’s I’m still working on resolving emotionally, perhaps it’s because it’s how I was brought up, perhaps it’s because I work in the industry and paying retail for anything makes me annoyed. But in capturing the items I wear throughout a week it often ends up being the same few - and it’s the few that I wasn’t afraid to splurge a little on (ok fine one was a gift from my husband but still). As I plan to fill in some holes in my wardrobe, I’m keeping that in mind. Sometimes, spending a little more on something you really love, will last forever, and is of excellent quality is worth it (and beats spending that same amount on 20 things you’ll only maybe wear on occasion).

the blazer that was more of an investment than I normally make, and I wear it at least once a week

So, with that, here are a few things I have on my spring shopping list:

• Sporty, comfy sneakers that aren’t Solomons. Probably something similar to these because all the cool girls in NYC are wearing them right now.

• A big grey sweater. My dream sweater is the Ophelia from The Row, naturally, but because I just can’t afford that price point, I’ll likely go here or here (yes, Quince, I know, I know, but honestly it looks like a great sweater!).

• A big cream sweater. I was debating this, which I recently bought in black and is as fantastic as everyone says, but I ended up with this, that I’ve written about wanting a few times. I actually met a reader irl over the weekend and she happened to be wearing it and completely sold me. So, thank you.

• Another pair of wide trousers similar to my favorite Madewell ones. Probably these, which aren’t just similar to my favorite black ones, but exactly the same.

• White barrel jeans. I have my eye on these that everyone seems to love. If you have them, talk to me about sizing in the comments below.

• A larger crossbody or sling bag I can fit at least a book in and at most a diaper, wipes, PBJ, granola bar, tissues, spare pacifiers, and Beaba sippy cup in. I love my Clare V fanny, but it’s no longer doing the trick. I’m leaning towards this one, which has the added bonus of being washable.

• A good pair of baggy overalls for chasing a toddler around a playground. If I was willing to spend more, I’d buy these, but I’m not, so I’ll probably buy these and wait for a sale.

• Fun summer flats. I don’t think the woven jelly trend is going anywhere, so I’m interested in something like these, but I refuse to spend that much for jelly slides and also walking around in a mule in the city is a non starter for me. So maybe these. And I just ordered these for our shop, so I plan to snag a pair for myself.

• Flattering basic tanks and tees that don’t break the bank.

  • On the tank front: I actually love a fitted rib tank a la this Gap Factory one I buy in bulk for pajamas, but often I find them not so bra friendly, which is a requirement for me despite the fact that I have small boobs. Breastfeeding, however, has turned those small boobs into flat little soggy pancakes, so I just generally feel better in a bra (my go to is this one, if you’re wondering). With that said, I’ll probably grab a few more of these Buck Mason muscle tanks, which I own and love.

  • I find myself in white tees nearly every day, either layered or just as is, and as spring and summer approach it’s time to stock up. As much as I love the Leset Margo, buying those in bulk isn’t in my budget, so I’ll probably snag a few of these instead. Out of curiosity, I asked ChatGPT what the best women’s white tee is and this is what it came back with:

    

    I would offer to wear test these for you guys, but not all of them are currently on the market. She’s a little behind the times.

• On my maybe list: a pair of knee length denim shorts (like these, or if I was rich, these) that I think will we see everywhere, and a poplin shirt/short set. I’m generally not a shorts person but I envision a lot of park time this summer with the baby, for which shorts will come in handy.

• On my “to replace” list: my running sneakers, like asap, especially since I’m trying to get back into early morning runs and have bad knees, my favorite Lululemon Align leggings that have held up really well but are on their last leg (I tried the Amazon dupe and they aren’t as good!), sports bras that no longer fit, my Converse high tops that I’ve worn so frequently the sole has separated from the rest of the shoe. Also, I plan to get this plain white oversized cotton button up to replace an old one that is stained beyond saving and I’ve nearly worn through.

• Because I’m sticking to my one in one out promise, I also have a list of things to part with, including an old Westerlind jumpsuit, a couple of striped button ups I never find myself reaching for, a black sequin dress, and a whole bunch of Chimala jeans I can no longer button. One day I’ll get around to listing them all on Poshmark, but if anything listed above piques your interest DM me for info.

What else are you guys shopping for this spring, if anything?

xx

jen

**I’m ignoring here the obvious disastrous state of the world we are living in right now, which is generally terrible and depressing and I’m choosing not to address it in this post. It’s not fine. I’m not fine with it. Things are dark. And going to get darker, I think. But that’s all for another post, maybe.