The winter packing series continues! So far, we’ve covered what to bring, how to fit it all in a carry on, and now it’s time to show you how I combine these pieces to make outfits for each day.
In case you need a quick refresher, we’re looking specifically at this packing list. My goal was to pack athletic clothes, weather clothes, fancy clothes, swimwear, and regular clothes (like PJs and travel clothes) all in one carry-on suitcase. The good news? It worked, and you can see the video proof right here.
So let’s jump into the daily looks I’ve created from the items in my suitcase:
DAY 1: TRAVEL + DINNER OUT
This travel outfit is easy and comfortable. I always feel put-together in a simple sweater, jeans, and big tote combo — and sunnies.
Once we land, I could throw on a long necklace, and this outfit will take me straight into dinner — no need to change.
To free up space in my carry on suitcase, I’m wearing my bulkiest items on the plane — including my black ankle booties and cognac cocoon coat.
Remember my friends Jess Lively of the Lively Show Podcast and Jessica Doll of Hej Doll from Wednesday’s post? If you haven’t bookmarked their blogs yet, you’ll want to right now. Both of them are travel pros, so I asked them for their sage advice on travel coats:
- Jessica Doll: I’ve had the Stadium-Cloth Cocoon Coat from J.Crew in black for years and it’s the perfect mix for warmth and style in a variety of scenarios. Though, if I’m going skiing or somewhere more adventurous I’d probably bring my Spiewak Aviation Eskimo Parka (it’s made with recycled down!).
- Jess Lively: Right now I only own one coat… so I’d have to go with that one! It is a mid-weight wool coat with a little leather detail on the sleeve. It’s similar to this one or this one.
DAY 2: HIKE + DINNER OUT
Woohoo! I’m most excited about this day because this girl loves day hikes. So I’ll be wearing yoga leggings, my base layer tee, Patagonia jacket, and running shoes. For a little color and interest, I’ll add my beanie on top.
I’m also bringing my swimsuit because we may stop at a hot springs on the way back. But even if not, hot tubbing is definitely on today’s agenda.
Later in the evening, we’re headed out to dinner — nice but not fancy, so I’ll dress up my jeans with my black ankle booties, crossbody bag, and long necklace. On top, I’ll add a little interest (and warmth) by layering my striped turtleneck underneath my black sweater. Finally, I’ll top it off with my cocoon coat.
DAY 3: SIGHTSEEING + NIGHT AT THE THEATRE
We’ll be walking around a ton today, plus it’s going to be cold and slushy, so I’m designing my outfit around comfortable, warm shoes — my weather boots.
(If you’re not into the duck boot look, here’s a sleeker waterproof bootie that can be dressed up, too.)
For the rest of the look, I’ll wear a base layer underneath my striped turtleneck. After yesterday’s hike, my base layer will definitely need a good steam with my sanitizing travel steamer or a quick wash in the sink. However, my turtleneck should still be nice and fresh since I only wore it to dinner last night.
Then, I’ll top it all off with my coat.
Later, we’ll be heading to the theatre for our fanciest night out, so I’m wearing my cashmere dress with coated leggings underneath, chic black ankle booties, and of course, my coat. I’ll also add a long necklace and my small black crossbody bag. This is my go-to look when I want to be dressed up but comfortable (leggings!) and warm (soft cashmere dress!). Win win.
DAY 4: MORE SIGHTSEEING + DOWNTOWN DINNER
Another day out and about in the cold and slush, so I’ll be back in my weather boots today. Even though these may not be the chicest of boots, they sure are comfortable, warm, and right for this particular trip.
I was curious about Jess + Jessica’s favorite travel shoes, so I asked them. Here’s what they had to say:
- Jessica: For city trips, my white Veja Esplar Sneakers are perfect. They’re flat, comfortable, and versatile. For more adventurous escapes, wool-lined duck boots like the UGG Cecile (I lived in these for my trip to Iceland).
- Jess: Brown leather booties! I can get a lot of wear out of a good pair of booties in cold city temps.
For dinner later, I’ll wear the same outfit but just swap the weather boots for my dressier black ankle booties, swap my day tote for my crossbody bag, and add a necklace.
However, if I did want to change and freshen up a bit for dinner, I could easily re-wear my theatre outfit from last night instead.
DAY 5: BRUNCH WITH FRIENDS + TRAVEL
Last day! In the morning, we’re grabbing brunch with some old friends at a cute little spot. Then it’s back to the airport for a day of travel.
I’m wearing the exact same outfit as Day 1 because (A) it’s a cozy, comfortable travel outfit and (B) I need to wear my bulkiest items on the plane to free up space in my carry-on suitcase.
KEEPING CLOTHES FRESH WHILE TRAVELING
Over the course of this trip, I’ll have worn my white sweater twice, my black sweater twice, and my striped turtleneck twice.
The key to making it work?
In my opinion, it’s all about three things: wearing base layers (it creates a barrier between your sweater and your skin, keeping sweaters cleaner, longer), using a steamer (steaming sanitizes clothes by actually killing any bacteria that might be lurking in the fibers — because of that, it can even remove faint odors), or giving your clothes a good ol’ hand washing in the sink.
But! How about another perspective? I asked Jess + Jessica how they keep their clothes clean when they travel. Here’s what they said:
- Jessica: As soon as I arrive at my destination and get settled, I unpack all of my clothing and hang it. I find that keeping it in my suitcase for the shortest amount of time possible helps with freshness, and wrinkles. If I have spare time or a special event, I take an iron to them on the first day as well.
- Jess: Staying in Airbnb’s with washers. : )
• • •
And there you have it!
Want to see the whole week’s worth of outfits in one simple graphic? Here you go! Feel free to save it or pin it for your future packing inspiration.
Tomorrow is the last post for the winter packing series, and it’s going to be a fun one! I’ll be sharing what I bring in my travel tote + how I keep it organized for the plane.
See you then!