In what feels like a blink, the morning walks and runs with the pups require more warmth, and out go the linen shorts and t-shirts and on go the wool gloves and stocking caps.

Last month during a walk in the snow near Bend with good friends and their two cavaliers, my friend Greg captured and created the short video you see below and kindly shared it with me. Kirby and Ranger along with Norman and Nelle took us for a walk is closer to what actually happened 😉 as their joy of romping about truly is energizing. What also made it thoroughly enjoyable was wearing the right clothing. And in so doing, not worry a drop about feeling comfortable and instead focusing on the time and conversation with each other alongside the beautiful winterscape. Upon sharing a few stills of this video on IG, many of you asked about my winter wardrobe for walking the pups, so I wanted to bring today’s post to you.

*Again, thank you SO much Greg for your video. It brings oodles of smiles just to see it again. I treasure these moments with the pups and friends who love their pups just as much as I love Norman and Nelle. xo

Before I dive into the four outfits I have shopped, I wanted to share with you some essential ‘rules’ I have found after taking daily walks over the past nine+ years here in Bend, Oregon, most in the morning and evening, so the chillest parts of the day. This year I have added taking weekly runs with Nelle, so I have also included a running outfit. The rules below are essentially guidelines I trust that so long as I don’t forget them, I will always feel comfortable, be able to walk or run with ease, and never have to abandon an excursion because I am ill-attired.

1. A scarf is a must unless you are wearing a wool or cashmere turtleneck sweater under your coat (or a run is in the plans ;)).

2. Don’t fuss with covered fingerless gloves – the removal ‘cover’ will annoy you and eventually rip off.

3. You really can just wear leggings if you are going running otherwise you will get too hot, just wear the layer or type of fabric designed for warmth (but not too much).

4. Always have your ears covered.

5. Cover the ankles, but not with heavy wool socks, just good socks.

6. High quality puff coats are worth the investment and aren’t as ‘puffy’.

7. Pay for quality cashmere or wool so it isn’t itchy.

8. Short coats (hitting at the waist), are not a great choice for winter, even if running, choose a jacket/coat that falls at least just below your waist (for walking, choose one that hits at least at your hamstrings)

9. Make sure the boot and/or hybrid shoe is waterproof.

10. Sunglasses in winter – yep, definitely a must in Bend with our Blue Bird Days – ‘sporty’ glasses aren’t necessary unless you are skiing/winter sporting it, and even then I still just grab my Ray Bans.

11. Thermal clothing isn’t necessary unless you are in an extreme situation or sport. Just layer well with natural fibers and an water-resistant outer shell – wool, cashmere, etc.

A quick note on all of the brands and items I have selected below: You will notice I have shopped all of the items you see in the video above (parsed out into different outfits, piece by piece). I have also tried to categorize each outfit, but no doubt, you will want to mix and match based on your needs, style and comfort. All outfits have gloves, so even if you see a fingerless style in one, don’t worry, I have full-coverage gloves in other outfits as fingers will need to be covered in very cold weather. 🙂 All brands are brands I trust, love and most I have purchased from. For example, I don’t go anywhere without my Eric Bompard cashmere stocking cap. An investment? Yes. Worth every penny? Oh yeah. Some of the styles are what I wear, but the brand may be different based on what is available now. The only item/brand I haven’t tried or know anything about is the running shoe for winter traction, but it comes highly recommended from Runners’ World (2024). And lastly, the scarves shared below are what is available now. My own collection of scarves has been gathered over years and from my travels. The ones shown below are from trusted brands and chosen for their color, quality and design to work with the other pieces of the outfit.

And, I didn’t forget! Four books have been thoughtfully chosen because, well, that is just what we do here on TSLL – bibliophiles that we are! After all, what is winter without oodles of books to snuggle in with when we return home after our outdoor strolls, runs and wanderings? 😉 Two books of the books shared below will be released in the coming new year, and the other two were released in the past couple years – one book is ideal winter inspiration for snuggling in and savoring this season, and another is the book to read when you are ready for the snow to go! 🙂 Happy reading!

Now to shop, to stay warm and be comfortable during winter when you take yourself and perhaps the pups as well for an outing in the winter weather! Enjoy! And if you have any questions, let me know in the Comments’ section. I am happy to help if I can.

Cold, Hike or Walk in the Snow

Depending upon where you will be walking and the weather, having sunglasses ready to go that are light-weight, but also sturdy at the same time is a must here in Bend. Ray-Ban fits this need the best and suits an outdoor walk outfit just as nicely as they do a more dressed up look. A very versatile pair that I have had for almost ten years. Regarding the gloves, rest-assured, I have full-coverage gloves below, but wanted to include the fingerless option here (much preferred for walking the pups and picking up after them). Mix-and-match based on your needs and the outing. Also, the jacket above is a wonderful jacket to wear with outfits shared below.

~Title Nine Cold Killer Pants, three colors, different fits/lengths, etc.~

~L.L. Bean 8″ boot~

~Barbour Tummel Quilted Jacket, three colors~

~Eric Bompard, 100% cashmere, loose rib, autumn white (this is the one I have had for four years and absolutely love – so soft, large, and warm)~

~Nordstrom Rack, fingerless cashmere gloves, three colors~

~Ray Ban’s classic aviator~

~The Scandinavian Guide to Happiness: The Nordic Art of Happy and Balanced Living with Fika, Lagom, Hygge and more! by Tim Rayborn~

~SHOP THE OUTFIT:

Moderately Chilly (25-35 degrees), Long Stroll on a Well-Worn Trail

This is the outfit I wore in the video above (the stocking cap I wore is linked in the previous outfit, but the brand here is the same). Also, my boots were shared above, so I found a different style for this outfit. I love this outfit when the weather is cold, but not far below zero. Perhaps I know the sun will eventually come out, or I will be moving at a brisk clip. Either way, I know I will keep my body temperature up because I will be moving, thus the jeans work perfectly.

This jacket has prompted more unsolicited compliments from strangers when I walk down the street, and I have been wearing it for three or four years now. I absolutely love it. It hugs me well, but is not too snug. The sleeves are long enough, and it is super warm (too warm for running), but not puffy at all. Hitting below the waist, my backside stays warm, but I can move well without feeling too swaddled. The only difference in the coat that Lululemon now sells and mine is that my hood is detachable and they no longer make that an option. Otherwise, it is the same jacket. Highly recommend.

~Madewell’s The Perfect Vintage Jean, high rise (two washes) OR Madewell’s Stovepipe Jeans, Lawlor wash (mid-rise), more washes~

~Sorel Kinetic Waterproof boot, more colors~

~Lululemon Down for it All jacket, (four colors available)~

~Eric Bompard cashmere Fair Isle hat, four colors~

~Bombas socks (soooo many sizes, colors, styles)~

~House of Bruar cashmere Tartan scarves, multiple color options~

~REI liner gloves (not too hot, but perfect on a mid-winter day~

~Travels through the French Riviera: An Artist’s Guide to the Storied Coastline, from Menton to Saint-Tropez by Virginia Johnson~

~SHOP THE OUTFIT:

Cold (maybe even windy) Outside, Casual Stroll in Town

This is the outfit I wear just about every evening when I take the pups for our evening constitutional in the neighborhood, or a slow, leisurely stroll in the heart of Bend, maybe to do some window shopping or watch the Christmas parade. You can move easily in this, your entire body is warm even if you aren’t walking too swiftly.

~Sweaty Betty Winter Explorer Pants (navy or black), 50% off~

~Columbia’s Moritza Shield boot, three colors available~

~Lands’ End Wanderweight Packable down coat, five colors available, on sale~

~Eton Prince of Wales Merino wool scarf, two color options~

~Quince Mongolian cashmere gloves, many colors~

~North Face Fur Pom Beanie~

~How to Love Better: The Path to Deeper Connection Through Growth, Kindness and Compassion by Yung Pueblo (to be released March 2025)~

SHOP THE OUTFIT:

Let’s Go For a Run – long or short distance – trails or in town

I recently saw someone wearing this simple color combination as they ran past me (we were walking), and I thought – how absolutely perfect, uncomplicated and stylish. I have the same essentials, just not that color of jacket, and now, I have my eye set on it.

~Lululemon’s Fleece high-rise running tight, 25″ or 28″, four colors~

~Lululemon Another Mile Jacket, five colors~

~Hoka Challenger 7 shoes, traction for winter weather, four colors~

~Trailheads’ Women ponytail running headband, two colors~

~Bombas running half-calf sock~

~Winter Wellness: Nourishing Recipes to Keep You Healthy When It’s Cold by Rachel de Thample~

~SHOP THE OUTFIT:

SIMILAR POSTS YOU MIGHT ENJOY

Winter in Paris — The 15 Essentials for Timeless Seasonal Style, episode #277

Thoughts on Winter Solstice: A Time for Renewal, A Time of ‘Great Beauty’ Waiting to Be Found

9 Ways to Lift the Winter Blahs

~Explore all of TSLL’s Style posts here.