We’re getting ready to head out of town, and, per usual, I have put off packing until the verrry last minute. I have done this – to myself – because I can hardly decide if I even like jeans anymore, much less which coats and shoes (and boots? Oof) will go with the baggy jeans I’ve been wearing all Fall. Now that it’s winter (or almost winter) what are my outfits?
Trying to figure out what to pack is basically like trying to figure out what I actually want to wear this winter, which feels like I must first figure out who I am as a person, what is the very specific color and shade of my soul, and/or if I were a cookie*, which one would I be?
Ya know?
similar puffer | jeans (28) | boots | bag | scarf | ring
*chocolate chip cookie, but with dark chocolate chips, flaked sea salt on top
It took me many (many!) attempts to get this winter capsule wardrobe right. I played around with baggy jeans, I played around with wide-leg jeans, I cuffed and uncuffed straight leg jeans, I even eyed up some skinny jeans (although I couldn’t bring myself to put them on). In the end, I identified a handful of pieces – a classic combination of sweaters, jeans, boots, coat – that all worked together. I often find capsule wardrobes boring, so I wanted to put together a winter travel capsule that would feel both exciting and practical (keeping cold, snowy climates in mind). So if you’re looking for a winter capsule wardrobe for travel, these 11 outfits cover everything from snowy mornings to casual holiday dinners.
And? I always start with the shoes, then the jeans. Everything else after that is a little easier.
My Winter Capsule Wardrobe: What I’m Packing For Holiday Travel (And Will Probably Wear All Winter Long)
In case you missed it, I ordered almost 30 pairs of winter boots and tried them on with a bunch of coats & jackets because I do think that having a coat-boots-jeans combo takes most of the effort out of getting dressed in winter. For this specific winter travel capsule, I wanted to include one pair of baggy jeans (since that’s all I seem to be wearing lately) as well as one pair of straighter, slightly cropped jeans, just for dealing with deep snow or slushy conditions. Because I’m focused on a holiday-ish capsule wardrobe, the baggy jeans I picked are an inky dark wash by AGoldE – something that can read dressier than most baggy jeans.
Additionally, while I do, admittedly, have something of a coat problem (Hi, it’s me, Collector of Coats), I really only want to pack one coat while traveling. And my favorite right now is a short puffer jacket that’s upgraded with some really beautiful textures: cashmere, faux-fur, or – my favorite – a heathered sort of gray. This is the kind of puffer that works for everyday use, but is elevated enough for a night out, too.
Anyway, I’m really happy about how this capsule wardrobe came together. It feels like me and what I actually do like to wear (jeans, boots, sweaters, puffer), but instead of my usual black-and-more-black (here’s last year’s winter capsule wardrobe), I was able to sneak some color in there…including two shades that have felt really current this year: chocolate brown & navy.
12 Winter Capsule Wardrobe Outfits To Wear All Holiday Season
Here are a few outfit combinations from my winter capsule wardrobe that I’m especially excited to wear. Most of these pieces are (or will be) on sale, so it’s worth clicking through on anything that catches your eye, but I’ll try to denote any sales I currently know of! I’ve also included a few additional swaps since things are selling out like crazy right now.
1. Cozy Winter Jeans Outfit (The Everyday Look)
sweater (s) | jeans (28) | boots | bag | necklace | ring
My classic winter outfit every year: cozy sweater, cuffed, straight-leg jeans, cute winter boots. Reformation’s Cove Sweater is a longtime favorite of mine, and I’ve gotten over my mad that this year’s version is 95% recycled cashmere, 5% recycled wool (instead of 100% recycled cashmere). The wool addition seems to help it resist pilling, and I’ve washed it like all my other cashmere with no ill effects.
Athleta’s gray flannel puffer jacket (old, here’s similar) is soooo pretty in person. The gray is soft to the touch with a lovely heathered look. When zipped, I can just tuck my cozy sweater inside and it stays put, comfortably.
similar puffer | sweater (s) | jeans (28) | boots | bag | ring
2. Cute Winter Brunch Outfit (Baggy Jeans + Sherpa Boots)
sweater (s) | jeans (28) | boots | bag | scarf | ring
It turns out that baggy jeans do work with cute winter boots, as long as the top of the boot has some interesting details. The vibe here is just really chill and easy but so cute. My striped sweater is 100% cashmere, but is the one cashmere sweater I own that doesn’t wash well. That said, I love the shape so much I have it in multiple colors. Also 25% off at Ref!
similar puffer | sweater (s) | jeans (28) | boots | bag | beanie | ring
3. Casual Winter Dinner Outfit (Sweater + Heels)
sweater (m) | jeans (28) | boots | bag | necklace | ring
Jenni Kayne’s iconic fisherman sweater – a piece I’ve owned for years – is good in soooo many situations. Add a statement necklace (I love this one) and some heels and I’m wearing it out at night, but it’s also slipped under my ski jacket as the warmest-ever midlayer. Quince makes a pretty decent dupe, however Quince’s navy isn’t as deep, the stitches are tighter (to account for the shorter yarns which effects the drape and pill), and the finished hems aren’t quite as pretty. But it is one of Quince’s better dupes.
similar puffer | sweater (m) | jeans (28) | boots | bag | ring
The heeled booties are Loeffler Randall, and they really are timeless. The shape is sexy, but the stiletto is shaped in a such a way that it’s sturdy and walkable.
4. Easy Holiday Party Outfit (Dressy Jeans + Silk Cami)
cami (s) | jeans (28) | boots | bag | vintage necklace (Victorian era!) | earrings | ring | bracelets
During holiday parties, I’m often ping-ponging between being too hot and freezing. 100% silk camis, worn under a cozy sweater, is usually my answer. This 100% silk cami is one of my favs (it comes in a few different colors) and is currently 25% off at Ref. Add a ton of fun accessories, and the resulting look is surprisingly festive and, depending on the accessories chosen, can have a pretty wide range of vibes.
One unsung hero of my winter wardrobe are sweater vests. I picked up this one at Sezane last year, and, happily, it’s back (with more colors added). It’s great for parties – adds a little warmth, but still leaves my arms bare, which means I can keep showing off my bracelets. 😉
sweater vest (s) | cami (s) | jeans (28) | boots | bag | vintage necklace (Victorian era!) | earrings | ring | bracelets
A quick moment for the jewelry – I’m wearing some seriously fun pieces, all from small businesses (most of them local to Philadelphia). They can all be found in our Holiday Shop – we (I?) basically looked for months, trying to find really unique pieces we actually would wear forever. The resulting collection is pretty darn foolproof – at least for my style sensibilities. 🙂
5. Polished Winter Night-Out Outfit (Warm Layers, Walkable Heels)
sweater (s) | jeans (28) | boots | bag | necklace | earrings | ring
That Ref sweater – she’s back! Added in some different accessories (and walkable heels) and I’m ready to head out for dinner. You can bet I have that silk cami on underneath, too.
6. Cute Winter Walking Outfit (Straight-Leg Jeans + Snow Boots)
sweater (s) boots | jeans (28) | bag | beanie | ring
If the snow is deep, or if if it’s wet and slushy, I don’t want my baggy jean hems dragging in it. That’s when I swear by cuffed, straight-leg jeans like this pair from Mother Denim. And I’m kinda obsessed with how the navy blue, brown, and merlot colorways all came together – even looks great with the cooler toned gray.
similar puffer | sweater (s) | jeans (28) | boots | bag | beanie | ring
7. Holiday Shopping Day Outfit (Cute Boots Edition)
sweater (s) | jeans (28) | boots | bag | earrings | ring
I like to make at least one shopping day feel a little fancy and festive – it’s holiday shopping after all, not just regular shopping. Holiday shopping looks like regular shopping, but with little treats sprinkled throughout (we’ve gotta stop at a chocolate shop somewhere) and ends with a happy hour drink. Says me.
This mix of casual and fancier pieces is perfect – and these boots are wildly warm, easy to walk in, and soooo cute.
8. French-Girl Winter Look (Vest + Perfect Tee)
sweater vest (s) | tee (s) | jeans (28) | boots | bag | ring | bracelet
That French-girl sweater vest looks so freaking cute with a t-shirt peeking out – of any color, really. And yes – the tee is rag&bone, my longtime favorite basic tee.
And since we’re leaning hard into French-girl territory anyway, why not a scarf instead of a necklace?
sweater top (s) | tee (s) | jeans (28) | boots | bag | scarf | ring | bracelet
This scarf, btw, is from a small brand who works directly with a family-owned factory in the Philippines, and creates their designs using only deadstock yarns. The results are really playful, offbeat designs – like this gorgeous scarf. Super soft and statement-making.
9. All-Navy Winter Outfit (Monochrome Moment)
sweater (m) | jeans (28) | boots | bag | ring | necklace
It wouldn’t be a capsule wardrobe from me if I didn’t include at least one monochromatic outfit! And here I am, replacing my usual all-black with…DRUMROLL PLEASE….da da dadaa: alllllllll navy, baby.
I’m crazy like that.
But also: see how cute the snowboots look with baggy jeans? It’s the tops, Gang. The tops (toes?) of boots matter when wearing with longer, looser denim styles.
10. Effortless Winter Errand Outfit (Oversized Hoodie + Dark Denim)
sweatshirt (s) | jeans (28) | boots | bag | ring
When I’m doing the car-to-store-and-back thing, a big ‘ol cozy, oversized hoodie is all I need. And Lululemon makes some of the best. It’s so snuggly on the inside, but feels smoother on the outside (almost like it might be windproof – it isn’t fyi). In short, though, it does feel like a winter sweatshirt. That said, I happily wear this one inside, too.
11. Early Morning Coffee Run (Sweater + Sweatpants)
sweater (s) | sweatpants (s) | boots | scarf | bag | ring
Just woke up and want to grab coffee in whatever city you’re exploring? My move is to just make sweatpants cute enough. Easy to do with a big, cozy sweater, cute scarf and boots.
12. Comfortable Winter Travel Outfit (Airport-Approved Layers)
sweatshirt (s) | sweatpants (s) | boots | ring | suitcase | headphones
My exact outfit for the plane (or a road trip). The hood is glorious, if you want to just put on headphones and tune out the world.
The Exact Pieces In My Winter Capsule Wardrobe (Quick List)
Here’s the exact formula (and pieces) I used to build this winter travel capsule (linked where applicable).
- 1 winter coat: Athleta Halo Puffer (gray heathered flannel) – sold out, similar here
- 2 pairs of jeans: AGoldE baggy jeans (dark wash) + Mother straight-leg jeans (cuffed for snow)
- 2 winter boots: one warm snow boot + one cute/walkable boot
- 1 heeled boot: for dressier nights out – here
- 3 sweaters: a fisherman knit, a striped cashmere, and a cozy Ref sweater
- 1 sweater vest: great for parties or layered looks – exact one, here
- 1 silk cami: perfect under sweaters or for holiday outfits – exact one, here
- 1 white tee: a classic layer – exact one, here
- 1 sweatshirt + 1 sweatpant: for travel days, coffee runs, and early mornings (I like these sweatpants and hoodie)
- 2 bags: one everyday bag, one night out bag
- Accessories: scarf, beanie, simple-but-statement jewelry (ring, earrings, chunky necklace, sexy necklace, bracelets)
How To Build a Winter Capsule Wardrobe (An Easy 5-Step Method)
In case you’re looking to build your own winter capsule wardrobe, there’s a process I always follow for these travel capsules (at least the winter ones) and it makes everything so much easier:
- Start with boots – these are the hardest. Figure out how technical your boots need to be (lots of snow? slush? ice?) and then start with your most technical pair. Fancier shoes are easier to add – they go with more jeans than snowboots, typically.
- Pick two pairs of jeans – one pair that’s cropped for snow (these must look cute with your most technical snow boots), one pair that’s a little more dressy.
- Add the coat – proportions are tricky, so try on coats and jackets with your chosen boots and jeans. (When in doubt, a short little puffer will go with basically everything, and can be dressed up or down).
- Sweaters & tops – Once jeans, boots and the coat are locked in, sweaters and tops fall right into place.
- Go nuts with accessories (scarf, bag, jewelry) – this is where I add personality, and where a winter capsule suddenly starts feeling fun. And it’s easier to pack a bunch of accessories than a bunch of bulky sweaters, so don’t be shy with the bags and gems. 😉
That’s it!! If you’ve been stuck for outfits, hopefully this helps! And let me know if you find the overall process helpful – it’s simple, but has been really working for me.
xo,
S
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