Three Things I Pack for a Winter Weekend
Embracing winter in Old Montreal — warmth, style, and a sense of adventure.
Packing for a winter weekend comes with its own set of challenges. Cold-weather clothes are bulky, space in your bag disappears quickly, and the forecast can swing from clear and cold to sleet or snow. The goal is to be prepared for the elements without giving up style — and to do it without overpacking.
For me, the simplest way is to focus on three essentials that cover warmth, function, and versatility: sweaters, boots, and a coordinating hat-and-glove set.
1. A Curated Collection of Sweaters
A curated mix of neutral and detailed sweaters — the foundation of my winter weekend packing list.
I always start with knitwear, since sweaters take up the most space in a bag, but are also the foundation of winter outfits. On a short trip, I bring two: one neutral that layers with everything, and one with fun details or a pattern — a fair isle, stripes, a knit with buttons or a patch, or even a touch of metallic.
The neutral becomes my base: a classic crewneck or cardigan that works with denim during the day or layered with a skirt or over a dress at night. The second sweater offers variety without requiring me to pack multiples.
When adding sweaters to my closet, I look for quality and fit. Wool and cashmere are my go-tos for winter: warm without bulk, long-lasting when cared for properly, and comfortable to layer. I avoid overly oversized shapes and prefer designs with detail. Over the years, I’ve kept a small collection I return to season after season when I travel to cold weather climates— a camel v-neck, a coffee-colored polo, a powder-blue v-neck, a fair isle, plus a few striped and detailed knits I’ve added along the way.
Shop the Look:
Investment:
White + Warren — U.S. knitwear label sourcing cashmere through certified Mongolian suppliers under the Good Cashmere Standard®.
Jumper 1234 — British brand producing small-batch knits in Mongolia with traceable cashmere and wool.
Naadam — transparency-driven company partnering directly with Mongolian herders and publishing annual impact data.
Secondhand:
Pre-loved cashmere or wool sweaters on The Real Real, Vestiaire Collective, or Etsy Vintage.
I gravitate toward materials and makers with traceable origins — pieces designed for warmth, longevity, and accountability.
2. Weatherproof Boots
Weatherproof boots that handle snow and city streets — stylish, practical, and ready for winter travel.
Nothing makes or breaks a winter trip like footwear. Streets can be slushy, sidewalks icy, and the best way to explore is still on foot. I always bring one pair of boots that can handle both the weather and the day’s plans.
I still own a pair of heavy-duty snow boots from when I lived in a colder climate, and they’re reliable in truly harsh conditions. Now that I’m in a tropical climate, I don’t need weatherproof lug ankle boots day to day — but if I lived somewhere colder, they’d be one of my first investment pieces. The right pair works across situations: walking during the day, managing unpredictable weather, and still refined enough to wear at night.
When choosing boots, I look for waterproof leather or suede, reliable traction underfoot, and a low, walkable heel. If I know I’ll be in snowy conditions, I want insulation, a higher shaft for coverage, and a tread that grips on ice. Boots may be something you buy new — January sales are often the best time — but they can also be found secondhand. Many high-quality pairs show up barely worn, sometimes even new, on resale platforms.
.Shop the Look :
Investment:
La Canadienne — handmade in Montreal using leather from certified sustainable tanneries; built for longevity and repair.
Nisolo — certified B Corp footwear made under verified ethical-wage standards in Peru and Mexico.
Sézane — French label integrating audited suppliers and an in-house repair program.
Secondhand:
Well-kept leather boots found on The Real Real, eBay Authentic, or local consignment.
Footwear worth packing is built for miles, weather, and years of wear — not just one season of style.
3. A Coordinating Hat and Glove Set
A coordinating hat, glove, and scarf set — small pieces that pull every winter outfit together.
These may be the smallest items in my bag, but they’re the ones I wear every time I step outside. A matching or coordinating set instantly elevates and brightens up a winter coat while adding warmth without taking up space.
I keep a few sets stored with my coat so they’re ready whenever I travel. Wool or cashmere are worth the investment — they block the cold, last for years, and feel better against the skin than synthetics. One of my favorites is a cream fair isle set I bought years ago; it still works with everything, a reminder that the right accessories don’t need constant replacing.
When I pack, I choose one or two sets that compliment my outerwear. It’s enough, and it makes every outfit cohesive once the coat is on.
Shop the Look:
Investment:
Cuyana— alpaca and cashmere scarves sourced through ethical cooperatives in South America..
N.Peal — heritage British brand using traceable Mongolian cashmere within certified supply chains.
Colorful Standard — organic-cotton basics made in Portugal with transparent dyeing processes.
Secondhand:
Vintage wool or handmade knit accessories on Etsy, curated local shops, or hand-knit yourself.
Small pieces, but lasting ones — warmth layered with care for where and how they’re made.
✨ A Note on Sustainability
The brands mentioned here are making strides toward more sustainable and transparent production, but no label is completely sustainable. The most meaningful shift comes from how we buy and care for what we own — choosing quality, wearing it often, repairing when needed, and keeping it in use for years to come.
Winter weekend ready: soft neutrals, walkable boots, and layers that work from city streets to cozy inns.
Why These Three Work
Sweaters, boots, and accessories create the structure of my winter weekend bag. They’re versatile enough to repeat, practical enough for cold-weather realities, and distinct enough that I still feel like myself. Once those are set, the rest of the packing list becomes easy.
Color, warmth, and texture: the building blocks of a winter bag that feels both practical and personal.
✨ Flight2Fashion Takeaway
Winter packing doesn’t have to mean heavy bags or endless options. It’s about identifying the few items that matter most and building around them. For me, it’s always sweaters, boots, and accessories — the foundation of a winter bag that works no matter the forecast.
✨ Want to put this into action? Download the Three Things I Pack template in Smart Packing section of the [Resources Library] — a simple organizer to define your own three essentials for every trip.
✨ Looking for inspiration? Visit the [Inspiration Gallery] for destination moods, color palettes, and outfit collections
✨Interested in reading more? Check out: How I Pack Layers for a 3 Day Weekend , ThreeThings I Pack for a Fall City Trip, and The ThreeThings I Pack for Thanksgiving..
✨ Packing well is only one part of traveling thoughtfully. If you want to plan trips that feel less rushed and more intentional, you might also enjoy → How to Plan a Trip That Matches Your Travel Style.
✨ If you’re trying to build a travel-ready wardrobe you actually rewear, this post pairs well with → Wardrobe Investments: How to Choose Pieces That Last.
A quiet pause in Old Montreal: where warmth, style, and reflection meet — the reward of packing well.
