What I learned from my styling session with Lisa

18 April 2022

You may recall last August, as I began to emerge from the newborn phase, I wrote about feeling ready to spice up my daily dressing: “After a year of just getting by in the fashion department – wearing what felt like the same four ill-fitting outfits on repeat – I’m eager for some variety and fun,” I wrote. “Even in between pregnancies, I’m guilty of switching out my top and wearing the same jeans, shoes, jewelry, and hairstyle five days a week. There’s nothing wrong with this … but at the moment, I’m feeling inspired to put a little more thought into what I wear each day.

In that post, I shared inspiration from my dear friend Lisa’s outfit diary series – I adore her style and lean on her for all my burning fashion questions (and rightly so!). In the post, I semi-jokingly asked whether she should come over for a styling session. Well, reader, she jumped right on that suggestion and before I returned to work from maternity leave, graciously came over and pawed through my closet with me! It was a delight, shockingly helpful, and really jumpstarted my return to having fun with fashion.

Ever since, I have been far more likely to put together interesting combos from my closet and put into play the four takeaways from my inspiration pull. Just for fun, I snapped photos of a few recent outfits to share, if you’d like to see. I’ll sprinkle a few more takeaways from my time with Lisa throughout, too!

The morning Lisa was due at my house, I pulled all the clothes from my closet and draped them over the sofa and chairs in our family room. I loosely grouped them into bottoms and tops, and set aside the items that I thought might need to be retired. Friends, almost everything that went into the “possible retirement” pile was, indeed, retired. Ha!

That right there was probably the most productive part of this whole exercise. It was so helpful to have a trusted friend who I could hold up a shirt and raise an eyebrow at and have her kindly agree that, yes, that had been so cute a few years ago, but it was not exactly current anymore. And if it was outdated AND it didn’t fit quite right, I didn’t love wearing it, or it wasn’t in line with the aesthetic I was moving toward? On it went to a new home.

Older clothes were not unilaterally destined for the donate pile, though! This pink tunic from Boden, for example, has been in my closet for probably 8 years. It’s one of my very favorite tops – I wore it for many Southern Weddings photos – but it was feeling a little tired and I wasn’t reaching for it as often. Lisa suggested doing a full tuck with it, and that simple move really brought it back to life.

On this day, I paired it with the Cali Demi-Boot version (Lockwood wash) of my beloved Madewell jeans, which I took a huge gamble on and bought half off on final sale last year. I felt confident to place the order since I love Madewell jeans, knew my size, and had seen this exact pair on my chic friend in person, but still, it was a relief when they arrived and looked cute. On my feet I’m wearing tan suede pointy toe d’Orsay flats.

When Lisa came over, we talked a lot about how I wanted my outfits to feel like Outfits instead of just jeans + tees, day after day. She immediately understood what I meant, and her advice (based on her own fashion journey of the past several years) was to buy a few items that felt really special. Yes, they would likely be more expensive. Yes, they might be more “trendy.” But if I didn’t want to feel like I was wearing the exact same thing every day, then I… needed to not wear the same thing every day. Ha!

You could say I took her advice to heart: Lisa arrived at our session wearing the shirt I’m wearing above and I promptly fell in love and bought the exact same one. It was a splurge, but the floral detailing is so beautiful and I really love wearing it. Also great for nursing! (It doesn’t look like the blue version is in stock right now, but they have it in white, and this top is lovely, too!)

If you’re unfamiliar with & Other Stories, here’s a pro tip Lisa taught me: when you click to the “all clothing” tab, you can filter by “atelier:” Los Angeles, Stockholm, or Paris. I like the Paris atelier, which has a more feminine, romantic style, best.

Here I wore it with my favorite 10″ rise Roadtripper jeans (seriously, nothing feels better than these jeans – they are so stretchy but hold me in in all the right places) and rounded toe navy Rothy flats. A note on the Rothys: my Mom passed them along to me (I think they were too small for her and she missed the return window), and though I wear them often, they always feel a bit pinched in the toe. I’m not sure if it’s just the style or if I should really wear another half size up? They’re very comfortable otherwise!

This dress was a fun purchase this spring! For the price, I was very impressed with the quality and the fit specifically – it nips in at the waist, the top doesn’t gap, etc. Also nursing-friendly! I’m pairing it with my jean jacket and the ankle booties that I’ve worn since 2015.

One thing to note: these outfits are mostly just for the people I love and for me, showing up as my best self in the world and having fun. I’ve been guilty of saving dresses and special outfits for special occasions, but it’s true: every day of this life is a special occasion. So, even though I mostly sat on my sofa and tapped away at my computer in this lovely dress, I felt great while doing it. You don’t need a reason to wear fun clothes that make you feel good (whatever that means for you!)!

This is not the greatest picture (hello, laundry!), but I had to include it because I just adore this shirt. The material is so light and gauzy and really takes it to another level. I actually own this shirt in two colors and two sizes – the white in a size XS and the dusty mauve in a size S. I like both of them and will wear both with a half or full tuck. Wearing with my favorite jeans here as well as my family bracelet stack – one each with the initials of John and each of my littles.

At one of the final photo shoots for SW, I dripped floral glue on a black-and-white striped shirt that was a mainstay in my closet. Until my session with Lisa, I couldn’t bring myself to get rid of it… but I also never wore it anymore because of the yellow blob on the front. Once Lisa gently pried it out of my hands, a classic striped tee was at the top of my replacement shopping list. After hearing good things, I ordered the Kule Classic tee in cream and navy stripes (size S). It was not inexpensive, but I’m at the point in my life where I’m willing to trade my money for my time and to pay for good quality (and sustainable practices!).

(If you are considering a Kule tee, I think this particular style runs a bit small. I’m happy with the fit, but it is a little slimmer than I was expecting. Also, it’s listed as navy stripes, but they read black to me.)

Here, I paired it with a pair of Clementine shorts. The color isn’t one I normally gravitate toward, but John actually purchased these for me and I’ve found it to be surprisingly versatile. My sneakers are gold and white New Balance from J.Crew, many years old.

This is not my most inspired outfit (nor the best photo), but I wanted to include it because of the pants! They’re a new purchase this spring and I really love them. The fabric feels like ponte, which means they are stretchy and comfy but also more formal in appearance due to the thickness and texture. I would recommend sizing down in these. I’m wearing them with a cream knit sweater, also from Old Navy many years ago, that I would never have considered tucking in until Lisa suggested it.

On my feet, I have leopard-print Birdies. I don’t find the slide style the easiest to walk in (I’m an energetic walker!), but love having a leopard print back in my shoe repertoire. These were a gift so I felt I could be a little riskier in the style!

Finally, here’s the same Kule tee with a full tuck. Paired with my favorite jeans and my go-to Allbirds, this outfit just feels classic and I love it. I heartily endorse this style of Allbirds (SO comfortable and versatile, plus made from sustainable eucalyptus fiber!) but would also heartily recommend wearing no-show socks, because I’ve found that the toes can wear out if you do not.

With every single outfit I am wearing my beloved pearl and gold earrings (demi size), and when I’m wearing glasses, they’re the Warby Parker Daisy in Oak Barrel.

One thing I loved learning in my survey data is that many of you not only tolerate, but appreciate that EFM is a bit like a box of chocolates – you never know what you’re going to get :) I hope this post has been just another example of that. If it’s not your cup of tea, no worries – we’ll be on to another topic shortly. If you did enjoy it, though, it would be helpful to know!

I’m also curious: have you ever done something like this? Had a friend, or even a professional, sort through your closet with you? I highly recommend it! (And thank you again, Lisa!)

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April 18, 2022 10:32 am

I’ve never done this with a friend, but I LOVE going thrifting with a friend and actually did this over the weekend. It is so fun but also so helpful to have someone you know and trust to be there as you’re trying things on.
That first picture – the pink top is absolutely adorable and I LOVE it with the full tuck!

April 18, 2022 12:13 pm

Never did this, but pre-pandemic I was a a dedicated Trunk Club subscriber. Trunk Club is (was?) Nordstrom’s version of Stich Fix. They had a in-house styling location in downtown DC and I actually had an in-person fitting with my stylist (Christina!), who I was pleased to learn was NOT a robot LOL I totally trusted her and was sad to see her leave during COVID. (In fact I think Trunk Club’s model has completely changed as a result of the pandemic.)

April 18, 2022 1:40 pm

LOVE seeing this!! That afternoon was so much fun, even though I feel like all I really did was tell you to tuck stuff in ;) You look fabulous in all of these outfits and I love that you’re having more fun putting new looks together! Can’t wait to get some Maylis into the mix too!

April 18, 2022 1:52 pm

I love this! I often miss the “olden days” of more long-form blogs doing OOTD posts :) and it’s fun to see the way you have freshened your look up and get some ideas in the process.
I just don’t know if I’m every going to be really *comfortable* tucking shirts into jeans though :/ I like the look on others but it makes me feel oddly exposed, haha.

April 18, 2022 3:56 pm

I love this kind of post! I’m dying to have someone go through my closet, if only to gently give me permission to retire some items. I have many that are 10+ year old staples that have probably seen better days but can’t let them go.

April 18, 2022 6:38 pm

I would love for someone to help me with my wardrobe! Since moving to Florida, I definitely wear more dresses, but would love ideas for how to style other closet staples (like shorts and basic shirts) in more interesting ways. I will definitely be checking out those Old Navy pants you shared as well.

April 20, 2022 9:02 pm

Love the mentality of rethinking how you wear your current clothes rather than just buying a whole new closet!
I know this wasn’t the feature of the photos… but I love your bed; any chance you could share where it’s from? (Relatedly, a few years ago you had a great post about the interior decor style you were going for – I’d love to see more decor posts from you if it’s something that energizes you!)

April 25, 2022 7:52 am

This has inspired me to start tucking things in. I have been a bit scared of the look as I am quite curvy but actually, it’s great.

May 3, 2022 2:06 pm

I just now have time to catch up on your recent posts!! This one is so fun, I love it!! Thanks for sharing all the great finds & tips!! You look amazing in every outfit, but my favorite one is the second last one! So classic! I would definitely be interested in more style posts! :)

May 5, 2022 5:26 pm

I appreciate the wide range of topics you cover!