Wardrobe Diaries: Home For The Holidays
Cozy but chic outfits, a couple of new accessories, and wardrobe resolutions.
MONDAY
When in Cleveland for the holidays, certain traditions anchor our visit. One of our favourites is attending a concert at Severance Hall, a venue as grand as the performances it hosts. Typically, we opt for one of the Cleveland Orchestra’s beloved holiday shows, but this year, my mum decided to shake things up. Instead, we experienced Canadian Brass, a quintet of virtuoso musicians known for their eclectic repertoire.
The program ranged from Coldplay’s "Viva La Vida" to show tunes and even classic Brazilian compositions, showcasing the group’s remarkable versatility. With a discography spanning over 130 albums—wow—it’s clear their artistry is as enduring as it is diverse. The performance was a delight, and I found it refreshing to hear brass instruments command the spotlight with such flair.
Still feeling under the weather, I aimed for comfort without (hopefully) compromising on style. A cream cashmere turtleneck provided a cozy foundation elevated by a silk slip skirt that added a touch of evening sophistication. Knee-high burgundy boots injected a subtle pop of color, complemented by bold, medallion-like earrings from a Chicago designer. The finishing touch was my Kurt Geiger evening bag, a versatile companion purchased in England three Christmases ago that gets a lot of wear. Cozy yet considered, it was an outfit designed for both comfort and understated elegance.
TUESDAY
Another of our cherished holiday traditions is a Christmas Eve morning visit to the Cleveland Museum of Art, a gem among American art institutions. This year, the spotlight was on Picasso and Paper, a sprawling exhibition showcasing nearly 300 works spanning the artist’s prolific career. Picasso’s output is staggering—an estimated 50,000 works across mediums, including paintings, prints, ceramics, and sculpture. As a person, however, he remains a complex figure (I’ll know more once I tackle Life With Picasso by Françoise Gilot, his former partner and the mother of two of his children). The exhibition, as expected, was masterful, offering glimpses into lesser-seen periods of his creative evolution.
For this cultural outing, I reached for my trusty red sweater—a Christmas Eve staple I thrifted IRL years ago. Its playful fisherman’s knit feels both festive and versatile, pairing just as easily with jeans or silk skirts as it does with tailored trousers. This time, I matched it with brown corduroys, a find from an early 2024 clothing swap. Though they sat unworn through spring, they are quickly becoming a seasonal go-to thanks to their perfect fit and rich texture. Completing the look were my go-to boots, scarf, and a crisp cream bag—a refreshing contrast against my darker winter palette. Practical yet polished for a day surrounded by masterpieces.
If you are sensing a theme here, you are right - we have our Christmas traditions down. For the past eight years—save for a few spent in Beijing and California—Christmas Eve dinner has meant a visit to Edwin’s, a charming French restaurant in Cleveland with an extraordinary mission. Staffed by men and women recently released from prison, Edwin’s provides a rigorous two-month training program to help individuals build careers in hospitality.
The restaurant’s founder, Brandon, a family friend, has expanded this vision to include a butcher shop, bakery, and additional dining establishments, all dedicated to supporting re-entry into society. His work is a testament to the power of second chances and has become a vital part of Cleveland’s community fabric. If you’re intrigued, Knife Skills, a 2018 Oscar-nominated documentary short, offers a fascinating glimpse into Edwin’s story.
The best part? The food is exceptional—classic French cuisine served with warmth and purpose. It’s no wonder this tradition feels so special, blending impeccable flavors with a profound sense of meaning.
WEDNESDAY
Christmas Day is a masterclass in relaxation for us: a slow start with a couple of presents, a leisurely brunch, and, more often than not, a trip to the cinema. This year’s pick was A Complete Unknown, the new Bob Dylan biopic starring Timothée Chalamet. It didn’t disappoint. Chalamet’s performance was compelling, and while I’ve long admired Dylan’s music, the film shed light on the formative years of his career in a way I hadn’t fully appreciated.
Outfit-wise, I kept it low-key but polished. My new ribbed trousers from Organic Basics strike the perfect balance between comfort and style—essentially elevated sweatpants. I paired them with a cozy sweater from another Cleveland favourite, The Fairmount, and topped it off with a faux fur coat to stick with a navy blue palette. The ensemble feels as suited to a day of festive relaxation as it does to a lazy Sunday, making it one I’ll be reaching for again and again.
THURSDAY
Christmas Day is a quiet prelude to the main event: Boxing Day, when we host our annual party at home. This tradition, started when my sister and I first left for university, has become a cornerstone of the holidays—a lively affair filled with friends, delicious food, and plenty of wine. These days, I opt for N/A reds, which means I can fully enjoy the festivities without dreading the infamous Boxing Day hangover.
For the occasion, I reached for one of my best finds from ThredUp—a Tory Burch sweater that’s festive without being over-the-top. It’s seen me through the holiday season, from a Harvard alumni gathering to a work event and now Boxing Day itself. It strikes the perfect balance of warmth, comfort, and style—a trifecta I require during the colder months.
I paired it with cream wide-leg jeans from sustainable denim brand Warp + Weft. After being somewhat neglected last year, they’ve become a winter staple. Winter whites and creams are so versatile, pairing effortlessly with the blacks, browns, reds, and navys that dominate my wardrobe. Together, this outfit feels like a celebration in itself—chic, cozy, and perfectly suited to a day of hosting. I want to wear it again and again.
This January, I’m committing to a no-buy month for clothing—a practice I aim to embrace four months out of the year. While the majority of my wardrobe is secondhand (as evidenced by my daily outfits), I recognize that I can sometimes go overboard, snapping up pieces simply because they’re too good to pass up. A pause like this encourages me to focus on what’s already in my wardrobe and appreciate its versatility.Â
Though I keep a running wishlist to fill specific wardrobe gaps, platforms like ThredUp and The RealReal have a way of tempting even the most disciplined among us—we’ve all been there. A no-buy month is my chance to reset, ensuring my wardrobe reflects intention rather than impulse. To stay on track, I’ve deleted the apps from my phone, announced my plan to anyone who will listen (accountability is key), and am genuinely curious to see which pieces and outfits I naturally gravitate toward over the course of the month.
This year, I am co-chair of the Conscious Closet Club at Chicago Fair Trade, and for our first meeting of the year, I created a template for monthly wardrobe resolutions and a list of ideas to inspire thoughtful choices. You can download the PDFs here and use them to refine your own wardrobe strategy.
WARDROBE ADDITIONS
A few new things have entered my wardrobe in the past few weeks, mainly because of gifts!
Shinola The Birdy 34mm watch—this was a huge (!) surprise this past weekend when my boyfriend gifted me a Shinola watch for our anniversary. I tried a couple of styles and ultimately went for this one because of its white mother-of-pearl face, gold and silver band, and classic but contemporary style. We are both big fans of the Detroit brand, and I am beyond thrilled to own one of their watches.
Jimmy Fairley The Meli Icons sunglasses—you may remember in my Mexico City post that I had added these sunglasses to my wishlist (after I tried my sister’s on and fell in love). Well, she gifted them to me for Christmas, and they are just as great as I remember. They are a perfect pair of sunglasses and such a thoughtful gift.Â
Chava Studio brown shirt—technically, I purchased this shirt in November, but they are made-to-measure, so it arrived over the holidays. I have yet to wear it out of the house, but I tried it on, and wow, the fit and the fabric are sensational. It is going to be hard to want to wear any other shirt ever again.
WARDROBE WISHLIST
Currently, the main things on my wishlist are:
Asket merino turtlenecks (in black and dark navy)
A pair of day-to-day flat winter boots (something like these Merrell Chelsea boots)
A couple of pairs of merino wool socks (like these)
A secondhand black leather belt
A secondhand pair of brown Tory Burch riding boots
A secondhand Etro sweater (like this)
I would love to know if you have any wardrobe resolutions or intentions this year and what items you are excited to be wearing this month!
Jennifer
xxx