The Art of Dressing
Dear Lovely,
The first time I remember recognizing that fashion was truly important to me was when I arrived at work my senior year in high school. I worked in the pro shop at a small, public golf course. It was winter, so I had forgone typical golf shop apparel such as a polo shirt and khaki shorts, and had dressed in black flare legged pants, you remember the ones from Express in the late 90s early 2000s. Anyway, paired with the pants were black platform loafers ala Clueless, a sheer button-up blouse in a beautiful shade of mauve and lined with a black spaghetti string tank top. To block out the cold, I wore a short, dark gray wool coat buttoned all the way up, and a wire headband with crystals.
When I arrived at work, I remember one of my coworkers commented about how well put together the look was, possibly even referencing Vogue or the streets of Paris. I highly doubt it was that impressive, but I remember while getting dressed, I had enjoyed the process of deciphering what I wanted to communicate through the look. In my own, seventeen year old ability, I wanted to look sophisticated and chic.
I went on to study fashion promotion at TCU. From there, I worked at both Nordstrom and Calvin Klein as a fashion stylist where I learned a lot about working with and dressing women (Nordstrom) and refined my personal style while developing an appreciation for American sportswear and couture assembly (Calvin Klein.) Since then, I’ve kept my finger on the pulse of fashion all these years, not by being employed within the industry, but just by paying attention to what was offered.
Mad Hatters Tea Party, April 12, 2018
Now as a woman in her forties, I feel like I’m entering a new age of my personal style, one that values creativity and nostalgia over labels and trends. I’ve also realized I often avoid overly feminine clothing, things with ruffles, bows, or exaggerated waistlines. This may be residual influence from my Calvin Klein days, or it might be to balance out my feminine features. Maybe it’s both.
The invention of social media—something that really bloomed after I left the industry—is a mechanism that allows a much easier glimpse into different fashion aesthetics.I look to European street style for inspiration more than anything else, which often consists of oversized garments with a masculine impression, showcasing multiple layers and fabrications, and spotlighting vintage pieces.
In my imagination, the woman who really nails street style utilizes creativity over affluence. She’s working class therefore can’t necessarily afford the latest trends; uses layers for warmth; snags old shirts from her father and brothers; highly values the 1 or 2 designer pieces inherited from an elderly relative; shops secondhand because that’s what she can afford, and somehow pulls it all together with a spritely, ragamuffin chic that looks interesting, authentic, and more stylish than most. This type of talent impresses me greatly; to not rely on a designer label or marketing campaign to know what looks good, but your own creative intuition. So impressive.
I told Brian the other day that I look at my clothes as art supplies, and whenever I have the opportunity to outfit myself, I love the creative process of pulling the pieces together, styling, if you will. I keep my clothes forever so I have lots of “supplies” to choose from. Because I work from home, and I am a team of 1, you would think I don’t have an occasion to get dressed for, but if fashion is your creative outlet, whether someone else enjoys the view doesn’t matter. I play dress up for me.
Sure, there are plenty of days that I pull on my favorite Pact Sweatsuits, but I get to have fun with socks, shoes, overcoats, scarves, hats, gloves and my creativity itch has been scratched. Sometimes I may even ask myself, what if I wore a bulky oversized sweater with my Pact sweatpants? What if I layered the scarf mom made me around my neck and wore my long black evening coat? This way I get to actually wear the things I love without worrying or wondering, do I even have an occasion to wear this?
St. Barth, Nov 6, 2019
Lovely, I’m writing you this letter give you my fashion background while also providing framework for how any future fashion letters work.
My goal is to always help you style what is already in your closet.
If something I’m wearing is is available to purchase still, I will always link it if you find yourself in need (or want) of the same piece. I will not link dupes or “something similar” because I won’t be able to attest to the actual fit or quality.
Disclaimer: I hope all of us in this community are also mindful of how we steward our finances and don’t fall for the consumerism trap that has hidden itself behind influencing, social media, “must-haves” etc. Not because those creators are bad people, but because the constant encouragement to buy coupled with a looping algorthythm has changed the norm of what’s appropriate, responsible, or necessary.
Because more and more of my clothing is thrifted, I hope to encourage you to appreciate the possibility of shopping secondhand. I know it’s not for everyone, and I understand that. However, when I saw the photos and videos of landfills with mountains and mountains of clothing due to the overproduction of fast fashion, it made my heart hurt for our beautiful world. (You can see a video about this on @itsme_kristen_d_ on Instagram. ) I hope if more and more people begin to enjoy shopping secondhand now and then, we will initiate global shopping standards that are more sustainable for the health of our world.
So to finish up this letter, I’m going to leave you with three pieces I am loving this winter.
a quality leather bag, larger than a shoulder bag, not quite so big as a tote. I love good leather purses, and so many are available secondhand or even at TJ Maxx. You really don’t have to splurge unless you just want to. This one was a TJs find last summer 👇🏼
2. ) @itsme_kristen_d_ owns Another Chance Resale and often has beautiful leather bags. That’s where I got both of these Coach bags. Soft burgundy leather and soft butter yellow leather. So good! (I’m not sure why the burgundy purse looks so dark inthe middle picture. I’m an amateur photog, friends, and using my trusty, dusty iPhone 11 ProMax…)
3.) an oversized blazer. I found this one at a thrift store in Paris and wear it at least once a week during the winter. It pairs perfectly over jeans, loafers, and a sweater. I love it with a mini skirt, tights and flats. I’ve worn it with a long silk dress and loved the mix of masculine and feminine.
4.) I know I’ve mentioned this before, but I am in love with my Pact Sweatsuits. I know you have your choice of sweatsuits on the market, but I think I love these because they are made with organic cotton. I add chunky sweaters in lieu of the jacket. And the jacket can be worn over leggings and a t-shirt to the gym.
Have a wonderful rest of your day, Lovely. And as always, if you have a fashion-y friend who would appreciate this letter, please forward it to them and encourage them to subscribe to The Art of Living Beautifully Substack.

