Holiday Style: Rewearing and Restyling the Pieces That Tell a Story
Pieces with Memory — a visual story of holiday traditions and the clothes that carry them.
Each year, the holidays bring a kind of nostalgia — memories of family traditions, the smell of recipes passed down from generations, and the sound of familiar songs that take you back to decorating the tree or opening gifts on Christmas morning.
In my family, Christmas meant an Italian dinner with lasagna, braciole, meatballs, antipasto, wine biscuits, Italian cookies, and gelato for dessert. We went to the Nutcracker or the Pops in the city, attended church on Christmas Eve, and spent Christmas Day with cousins. Even now, I try to keep some of those traditions alive with my own family.
Our family Christmas dinner always included lasagna, bread, and Italian cookies — traditions I still try to keep alive
Looking through my closet this December, I realized I have traditions there too — pieces with memories and stories attached, pieces that have lasted through years of holidays and are still worth wearing now. Just like our family recipes or favorite songs, these clothes carry the past into the present. Sharing them here feels like another way to continue the nostalgia of Christmas — to show how clothing can hold meaning, connect us to the people and moments we love, and still be restyled to work for today. Each one can be updated with a new layer, accessory, or shoe and made part of this season’s celebrations.
Outfits with history: cozy textures and rich colors that bring holiday traditions to life
Pieces with Memory
Charm Bracelet
I started this bracelet when I was twelve, and each charm marks a place I’ve visited, an activity I love, or something symbolic — like the tiny ladybug I added for good luck. Adding it to an outfit instantly makes what I’m wearing feel personal and reminds me of the moments I’ve collected along the way. Over time it has become a timeline I can wear, and it’s often a favorite accessory I reach for in December.
Suede Bag
This vintage suede bag, with its gold chain strap and clasp, belonged to my mom when she was dating my dad. Carrying it now feels like taking a piece of family history into the present — a small but powerful reminder that clothes can connect generations.
Brown Floral Silk Dress
This vintage silk dress has been worn to holiday dinners and events over many years. The silk lining, flattering silhouette, and rich floral print make it a piece that works across seasons. For the holidays, I’d pair it with gold shoes and jewelry for a dressier look, or more casually with tall suede or brown boots and a slouchy bag. If you love the style of my brown silk dress, I’ve linked a search on Poshmark so you can spot similar floral silk dresses by the same designer — just filter by your size and save what you like to watch if it pops up.
Lily Ashwell Silk Dress
This is from Lily Ashwell’s very first collection in Holiday 2012, a California-based designer who focused on local production, small-batch runs, and storytelling through vintage-inspired silhouettes. The delicate sleeve detail and floral print still make it one of my favorite pieces to bring out in December, and adding a simple heel or boot is all it needs to feel current. Her early pieces are hard to find, but that’s part of what makes them special. If you’d like to hunt for one yourself, I’ve linked a Poshmark search for Lily Ashwell — you never know what treasures might pop up.
Lily Ashwell Fair Isle Sweater
A true Poshmark find and one of my favorite secondhand scores, this hand-knit fair isle sweater is beautifully constructed and timeless. I love styling it with wide-leg dark denim and ankle or lug boots for a modern look, or layering it over a silk skirt or slip dress to mix textures. I liked a Poshmark search above for Lily Ashwell items, but Lily Ashwell pieces can also be found on eBay as well.
Marc by Marc Jacobs Metallic Trench
I bought this coat more than fifteen years ago, and it’s still one of the most versatile layers I own. The ivory buttons, vibrant pink print lining, and subtle metallic sheen make it perfect for holiday nights out — it elevates everything from denim to dresses. Marc Jacobs trenches show up regularly on resale sites. Here’s a Poshmark search and a RealReal search if you’d like to see what’s available right now. I did happen to see this exact trench on Poshmark in a few listings.
Burberry Scarf
A RealReal find that has quickly become part of my December rotation when I travel somewhere cold. I wear it with my camel coat or even a metallic puffer to add color. The classic plaid pattern means it will stay in my wardrobe for years and always remain in style. Burberry scarves are true classics, and you can often find them for much less secondhand. I’ve linked a RealReal search here if you’d like to browse.
If you want to start your own collection of pieces with history, I love Poppy’s Vintage Clothing. Everything is over 20 years old and carefully chosen, so every coat, dress, or bag already has a story. Finding something with that kind of character feels like adding a little piece of the past to your own wardrobe.
How I’m Styling Them This December
Even though I live in a tropical climate, I love bringing these pieces into rotation this time of year — and when I travel to a cold-weather destination, I style them a little differently. Here’s how I’m wearing (or planning to wear) them this season:
My 15-year-old vintage silk floral dress, styled with my charm bracelet, and my vintage suede gold-chain bag and paired with Loeffler Randall tall boots — proving timeless pieces never go out of style.
Marc Jacobs trench meets a Lily Ashwell dress, sparkly gold shoes, my vintage suede gold-chain bag, and my favorite charm bracelet — a classic look for the holidays
Charm Bracelet: Goes with everything from casual to dressy outfits — perfect with a sundress at home or with a cozy sweater when I travel to a cold-weather climate.
Suede Bag: Works year-round here; I love it with linen and sandals in warm weather and with tall boots + dresses if I’m heading somewhere cold.
Brown Floral Silk Dress: Gold sandals or block heels for holiday dinners here; suede boots + cardigan if I’m traveling to cooler weather.
Lily Ashwell Pieces: The silk dress pairs with strappy sandals for Florida evenings. The fair isle sweater is too warm for home but comes with me when we travel — I wear it with denim and boots for tree shopping or brunch.
Metallic Trench + Burberry Scarf: The trench is light enough to wear over holiday dresses for evenings here, and the Burberry scarf is my go-to cozy layer for cold-weather trip.
Hand-knit Lily Ashwell Fair Isle sweater paired with dark wide-leg denim,a brown suede slouchy bag, brown ankle boots and my charm bracelet.
Timeless pieces from my closet-a wool camel coat, vintage Burberry scarf, Lily Ashwell sweater, dark quilted denim, brown ankle boots and my charm bracelet- updated with a brown suede slouchy bag.
Start Your Own Holiday Style Tradition
Looking through my closet this December reminded me that personal style is connected to memories and can tell your story. The same is true for you — your closet is full of pieces that carry your history. Some are family heirlooms, some you’ve worn to countless events, and some remind you of trips, milestones, or seasons of life.
Pieces with memory — my wardrobe favorites that carry family history and stories into the season.
This month, try building your holiday outfits around those pieces:
Choose What Tells Your Story: Pull out 3–5 items you’ve owned for years or that hold a memory — a bag from a family member, a dress you’ve worn to past holidays, or a bracelet from a trip.
Update Them: Add a new shoe, a different layer, or a fresh accessory to bring them into this season.
Wear Them to Create New Memories: Let at least one of these pieces be part of a gathering, dinner, or trip this month — and make it part of the memory you’re creating now.
✨ Want to plan your own? Download the Memory Based Holiday Workbook in the [Resources Library] to choose your core pieces and see how they set the tone for the rest of your outfits.
✨ Looking for holiday direction? Explore the [Holiday Inspiration Gallery] for seasonal color palettes, festive outfits, and mood boards to guide your December packing and read the guide Holiday Style: How to Look Festive Without Buying a Whole New Wardrobe. and the guide about Wardrobe Investments: How to Choose Pieces that Last.
✨Interested in reading more? Check out: How I Pack Layers for a 3 Day Weekend and ThreeThings I Pack for a Fall City Trip and The ThreeThings I Pack for Thanksgiving.
