no. 16: classic, minimal, whimsical

results from phase one of my adapted 75 hard style challenge

1. skinfix eczema+ balm: my dry, sensitive skin took an absolute beating this past weekend while skiing in Park City. Think: cheeks so chapped and reactive Mark asked me if it was a sunburn after a day of skiing in fog and snow.🫠 I’ve been layering this balm under my moisturizer at night, and am feeling noticeably soothed and hydrated.

2. maggie rogers, don’t forget me: maggie teased that she’ll be releasing her third album in 2024, starting with the single don’t forget me that she played on tour last summer. I’ve had a version bookmarked since last july, captivated by the familiar bittersweet worry of being left behind while friends all around you move forward: Oh, won't you promise me that when it's time to leave / Don't forget me. presave today, out 2.8

3. Lindsey Stanberry
   ’s
   The Purse
   : Lindsey, a founding editor for Refinery 29’s Money Diaries recently rolled out a new series called Home Economics. Similar to money diaries, HE deep dives into someones financial situation looking at monthly income, expenses, and general money story. I can already tell it will be a fast favorite.

   

no long preamble today, let’s just get into it!

If you’re new-ish here, fashion as a form of personal expression has always been something I looooooooooove. I wore a uniform all the way through high school, so the times I got to dress in “real” clothes always felt special – an opportunity to assert myself. In college, I was so successful in my two month summer job as a sales associate at J.Crew that at the end of the summerI was promoted up to be a stylist. I spent the remainder of my time in college commuting into Boston multiple times a week to meet with clients and build them a new wardrobe. The clothes, honestly, were secondary. The magic was the way the clothes brought out the version of themselves that they wanted to be. 

outfit feat. j.crew 2012: I still have and *regularly* wear the boots, belt and blazer.

My clients would come in for ever major milestones and life transitions you could imagine. New business formal jobs - to be taken seriously, but still show some personality. Meeting a new partner’s family, and then not long after, engagement photos, shower, rehearsal and bridesmaids dresses. Rediscovering style after having a baby. New clothes to fit a body that has changed. A mom and a young college student from a warmer climate on Parent’s Weekend, panicked about the upcoming weather forecast. 

My specialty wasn’t necessarily pulling the most fashion forward, high commission outfits. No, where I excelled was understanding the split-second reaction when they walked out of the fitting room and saw their reflection.  I would regularly encourage my clients to walk away from something that they wanted to love, but clearly didn’t. Almost as frequently,  I’d catch the look of sheer *joy* at something that pushed boundaries and quickly intervened before that joy could be snuffed out by worries that something was too much or unflattering. 

These experiences informed a lot of my own personal style - in addition to heavily padding my closet thanks to a generous employee discount and a light impulse control problem when it came to sale-based shopping. 

Even today, I think a lot about how I want the clothes I own and wear to function as an expression and extension of myself: whether I love them, of whether I just want to love them.

I love Allison Bornstein’s “three word” method to describe and curate your own style: 

• Word #1: Practical:  How do you describe what is actually in your closet that you wear all the time? 

• Word #2: Aspirational: What styles are you drawn to, or would you like to dress more like? 

• Word #3: Emotional / Feeling: What feeling do you want the clothes you wear to evoke, for you and to others? 

I’ve explored my own words a few times, and the ones I keep coming back to are: 

classic, minimal, whimsical. 

Classic: the Catholic School, J.Crew, Boston, influences die hard here. I am drawn to classic Ivy / Prep aesthetics and silhouettes. I largely gravitate to clothing that is functional: sweaters, button downs, t-shirts, vintage denim. 

Minimal: I prefer clean lines, solid colors, and lean towards neutrals and earthy colors (navy, blues, white, camel, sagey greens, the occasional pop of lilac). I select options with patterns or detailing sparingly. 

Whimsical: A dear friend helped me come up with this one, and I think it’s my favorite one. I love clothes that have a pop of the unexpected: a fun sleeve shape on a sweater, an unexpected monogram on a button down, classic-inspired pieces that play with proportion.

I have been very intentional about aligning purchases with these elements over the last few years, focusing on “fewer, better things”, and on clothes that really embody these words for me. And, for a while, I was doing great! I had a ton of fun in 2021 building maximalist capsule wardrobes based on things I already had, and truly loved getting dressed every day. 

(And then, you know, I had a baby. )

I’ll touch on how I approached maternity fashion soon, but post-baby 2023 was extremely strange for me, fashion wise. When I was pregnant, I donated a lot of clothes, and archived others that I knew I wouldn’t be wearing for a very long time - it was simply *not my business* if they fit me or not!. As my body changed post-partum, my sizes fluctuated every couple of weeks for months at a time. My historically barely-an-a chest was suddenly… way more than that. Clothes fit me differently from one day to the next and even then varied by the hour. 

It was certainly an exercise in non-attachment to release any judgement or frustration, about those changes (more than anything, it was just inconvenient - who has the budget to buy all new sports bras when you go up 2.5 cup sizes in the like 5 days? not me!!!!!!). I did my best to channel energy into a few staple outfits I knew would always work. But by the end of last year, I found myself feeling both bored and frustrated when I got dressed. I was wearing the same things over and over. I felt like things were missing from my wardrobe. Things I have had for years no longer felt quite like me. I had a sneaking suspicion I have too many of the wrong clothes. 

So! I decided to start the year with a modified version of the 75 Hard Style Challenge: an Internet Thing that encourages participants to get dressed every day for 75 days, avoid buying new clothes, and “shop your closet”.

Reader, I love a challenge (and more than that, I love data), so I decided to make my own modified version: 

• Phase 1 (Day 1-30) : Baseline. Document what I wore every day to understand what I *actually* wear all the time (versus what I “feel” like I wear all the time). 

• Phase 2 (Day 31 - 75): Baseline, but make it Fashion: This is where the “get dressed every day” part comes in. Time to be intentional about what I’m wearing, trying new things and new combinations to mix things up. 

• Phase 3 (TBD): ALL FASHION ALL THE TIME: (i’ll be honest I’m still working on what this one means. We’ll get there!)

Rules: no new purchases for the first 30 days, aiming for as few purchases as possible through the full 75. At the end of 75 days I’d like to do a closet audit and seasonal clean out based on the clothes I *haven’t worn at all* (a great indicator they are no longer a good fit!). 

All that being said: I recently finished the first 30 days, and I’m low key obsessed with what I’m learning: 

As part of my tracker for the project, I included the context (what I was dressing for or doing). I primarily work from home, usually going to the office 1-2 days a week, and I have a one year old, so it’s not surprising at all that most of my time is spent at home or on casual outings (dog park, walks, earrings, etc). I recently read and loved @Anna Newton’s piece  “Why are we buying clothes for lives we don’t have” where she provides an obvious buy eye opening recommendation to track your fancy / casual split on a month to inform future purchases. I feel like I “need” more chic blouses: data this month tells me that I dress casually… 73% of the time. Hmmmm. Maybe not. 

I’m not surprised by most of the things on my “top item types”, although it was genuinely sobering to see how often I wore leggings. While it is January, I do mostly work from home, and I included workout outfits here… I still wore leggings a solid 24/44 outfits (+50%!!!!!?!) of total outfits. While this isn’t bad, I don’t think it fully aligns with my personal style words, and is something I’d like to adjust in Phase 2. 

Interestingly, I found myself feeling similarly about how often I wear sneakers: I love sneakers, and for a long time they contributed the “whimsical” element to many of my outfits: however as time has gone on and they have become a staple element in my wardrobe, I find myself craving something more interesting - prompting me to finally commit to a pair of loafers I’ve been eyeing since November the minute this phase was up! 

for visibility: this next section of the post includes affiliate links. I’ve also included the full name of products (so you can search on your own if you’re so inclined) and approximate purchase date for everything listed below to give some context.

most worn items

The most worn items are a fairly classic example of my standard style, and many things on this list have been in my closet forever. of the things that haven’t been: it’s quite satisfying that two new purchases from December 2023 make this list (feels like an indicator they were worth the investment!) 

• Everlane Way High Jean: Originally purchased in 2021 - these are a classic straight leg jean with a high waist that are the most common pair of jeans I reach for. I find the inseam length I have works best with sneakers (and noticed over the month that I wished they were slightly longer). 

• Alex Mill Betty Sweater: Originally purchased Fall 2023: this was a “treat yourself” purchase after a big win at work (had been starring on my wishlist for at least two years). It’s an oversized wool sweater with perfect “whimsy” elements (larger sleeves, statement turtleneck), and I invariably get tons of compliments whenever I wear it. (this color is no longer available online, but there are a few secondhand options available!) 

• Sezane Conrad T Shirt: this is my perfect T Shirt (I have two purchased spring 2023) - I layer it under thicker sweaters or wear tucked into jeans. My whimsy addition: take advantage of the free embroidery option to add a monogram element. The lowercase cursive look of my initials is a little abstract, and I think it’s just *chef’s kiss*. Makes a basic white T-shirt feel intentional and elevated. 

• Everlane Sherpa Pullover: This is also a Fall 2023 purchase, so while I’m glad to see this one here (it’s so cute! It’s so comfortable!) It pains me a little to know that it was just the same outfit like 10 times (Pullover + white t-shirt + leggings + sneakers). Goal for Phase 2: make it more interesting! 

• New Balance Sneakers: Originally purchased Fall 2022. I reach for these more often than most other shoes in my closet because I love the pop of yellow. 1+ years on, I am finding that they are looking a little worse for wear, which is disappointing (note to self: suede and Seattle are not a great pairing). Goal for phase 2 is to see what I can do to clean them up. 

• Lululemon Wunder Train Leggings: I have been a diehard Lululemon fan for years (the only leggings I will run in, and this exercise has only solidified this for me. I have 4 pairs, the first of which was purchased in 2016. Doing some extremely rough math: say I wear them ~15x per month, for 12 months, for EIGHT YEARS?!?! 1440 wears makes that ~34 cent price per wear look AMAZING right now, y’all. (currently obsessed with the new lulu “like new” program with certified resale for second hand – so many options!!!!!) 

I did actually get dressed this month.

most worn fitness

A thing you should know about me is that I heartily embraced athletic wear as a fashion choice in 2010 and haven’t looked back since. For the purpose of this challenge, I differentiated actual fitness from casual outings (for the purpose of ~data~), but the end result was pretty much the same. I own a lot of athletic wear, and I wear it all. the. time.

• Lululemon Fast and Free Leggings: Originally purchased 2018. Interesting contrast to me from the wonder trains, above. fast and frees are a lighter fabric made for higher intensity workouts. I mostly wore these to the gym and on errands like dog walks. They are an all time favorite purchase, tied with the Wondertrain for most worn item of the month. 

• Lululemon Rulu Crop Running Long Sleeve + Align Tank: These were a December 2023 purchase (took advantage of the exchange rate while visiting Whistler) and I have been extremely happy with them. Clearly will make the long time favorites list.

• Lululemon Energy Bra: Originally purchased Summer 2015 - I’m honestly just so relieved that this fits me again after I stopped nursing. My favorite sports bra for higher impact activity, I’ve run 2 half marathons and climbed Mt. Kilimanjaro is this one. If the energy bra has no fans, I am dead. 

• Nike Invincible // Metcon Sneakers: My current athletic shoes of choice. I lean on the Invincibles (purchased Spring 2023)  for casual outings where I’m doing a lot of walking, and the Metcons for gym workouts (... mine are from 2017 and should probably be replaced. Don’t tell). 

• Halfdays ski-kit: Two different Ski Trips means I am slowly but surely chipping away at the PPW for some of the most expensive specialty gear in my closet. I originally purchased the bibs in 2021, and finally bought the jacket on Cyber Monday in 2023 at a discount after years of freezing in old thrifted snow gear. I’ve been extremely pleased with how functionally comfortable they are when skiing - warm without being too hot, waterproof in terrible conditions, and easy to move in. All that and cute to boot! 

PHASE 1 TAKEAWAYS AND INSIGHTS: 

You can’t know how you *want* to dress, and still not do it: 

I’m a big fan of the “dress for the life you have” approach (ball gowns and smart dressing isn’t going to make a ton of sense in the reality of my current day to day life). BUT, seeing what I’m actually wearing on a day to day basis right now is evidence that I’m *already doing that*.  Knowing I’m dressing practically but not in alignment with my aspirational fashion words makes how bored and uninspired I feel make sense, and now I feel like I have good data and a baseline for what I can adjust in phase 2.

Things I feel like I wear a lot vs things I actually wear a lot:

I was genuinely surprised by all but one of the things on my “most worn” list. I find I don’t consider the “basics” when I mentally categorize what I’m wearing all the time, opting not to wear a statement piece into the office again “because I just wore it”, when in reality that simply isn’t the case. A whole bunch of pieces I conceptually really love fell into the “0-1 wear” category this go around, highlighting some potential candidates to consider consigning if they aren’t making the “reach for it over and over” cut. 

Your life is a special occasion: burn the good candles.

 Thinking about getting dressed closer to my fashion words led me on a few different pinterest searches to consider how I could accomplish some looks I like with clothes in my own closet. A few iterations of this highlighted my tendency to avoid more “out there” styling I’m excited and inspired by, and to “save the good outfits” for special occasions (example: an adorable monochromatic workout outfit and I’m obsessed with and somehow never wear because I don’t want to “waste” it.) . A goal for phase 2: just full send it and start wearing the fits 

You don’t always need new (even the “sustainable option”!):

  I’ve been paying for nuuly out of my own pocket for ~3 years now (it was a god-send while pregnant and postpartum!). But now that my general sizing has stabilized, and in the absence of a special event or occasion, I found that I barely wore any of the “new” options in my monthly rental. I’m planning on taking a cue from my friend Kate who recently didn’t buy any new clothes for a full year (!!!!!!!) and keeping the option for trips and special events, but otherwise placing it on hold. 

…But sometimes there genuinely are gaps:

I just checked and a solid 65% of my inspiration images on pinterest include a type of pants I don’t currently have: either a wider leg, longer denim, or a more flowy trouser. I simply do not have either of those things, despite the fact that I have been contemplating purchasing them for literal years at this point. I tend to put off buying things that I know I want (“because I don’t need more things”) only to later impulse buy another sweater (“because I know i’ll wear it”). There is definitely a rightsized approach I need to take to commit to investing into the pieces I want to wear, and to release the desire to impulse buy things that don’t fill those gaps. One step in the right direction: I finally bought the loafers I’ve been contemplating for months, and have already worn them 5+ times. Clearly a case of an aligned purchase, and one that is a much better investment than 2-3 cheaper items that don’t fill that gap. 

This is my version of this challenge, so I took this week to collect my thoughts, and I’m planning on kicking off phase 2 next week. I’ve got my inspiration all queued up and ready to go to style items already in my closet and push myself on the fashion front. A few intentions I’m thinking about as I jump in: 

• Start regularly wearing the “special” pieces that I didn’t wear last month. 

• Re-align to my fashion words: A nice way of saying: no more leggings for every outfit, as comfortable as it might be. 

• Step outside my comfort zone: I know my fashion uniform in my sleep at this point, but I’d love to start pulling together more exciting styling: monochromatic fits, bringing out nicer jewelry I don’t regularly wear, etc.

Finally: A lot of y’all mentioned being interested in style me sessions through the newsletter, and I’d love to do a few in a bonus issue! Go ahead and submit requests for how I can help style and support ya in the question box, and please please please leave any comments about the challenge in the comments!