We’re doing a little travel over the holidays, and I — in a desperate bid to BE READY — have been trying to figure out what to pack. In this instance, “what to pack” is synonymous with “what do I actually WANT to wear this winter” because, as we’ve mentioned before, we* suddenly hate everything.

*We, in this case, is Laura and I. She blames “the change,” which feels odd to my 36-year-old brain until I look in the mirror and remember that I’m…46. Oooohhh, she’s riiiiiight.

Anyway. I need some winter outfit inspiration.

sweater (S) – 20% off | jacket (S petite) | jeans (26) – $100 off | bag – 30% off

I started, as I always do, by playing a form of paper dolls with winter coats and boots. Figuring out a coat + boot pairing makes getting dressed soooo much easier, and I can tailor the coats and boots to meet my specific requirements. For example, I always need a coat that’s warm but not heavy, and I need boots that are walkable, waterproof and warm enough. A sole that supports walking over icy streets is a plus.

I documented the first round of my paper-dolling (I guess that’s a verb now) in my November Style Notes, one of our downloadable guides. The intention of my style notes is to show some of the behind-the-scenes process that goes into building a working wardrobe. This shit isn’t easy (at least not for me).

Without fail, when I go through this sort of a process, I always end up with a capsule wardrobe that goes the distance, and I end up buying less. Even better, this “buy less” approach actually carries over for the next few years. When I’ve got a capsule wardrobe that works, it often only needs a small tweak (rather than an overhaul) the next year too.

My Winter Capsule Wardrobe: What I’m Packing For Holiday Travel

Once I played around with coat and boot pairings as documented in my style notes, I ordered a bunch to test out. (In fact, I’ll have a Sorel boot try-on video coming out soon, as a result of this process.) Serendipitously, I found jeans I actually LOVE (suuuuper-soft, suuuuper-comfortable), and the capsule wardrobe came together pretty quickly.

Even better? It turns out that most of the pieces are on sale for Black Friday and Cyber Monday. Sales are changing quickly (no guarantees), but I tried to document which pieces are on sale, below.

Speaking of Black Friday, have you checked out our BF cheat sheet yet? It’s our one-stop-shop for all the deets on Black Friday deals. And when you’re done shopping here, head over to Holiday Central for other holiday sales, gift ideas and more outfit inspo all in one spot. It’s a happy place.

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10 Winter Outfit Ideas: How I’ll Be Wearing My Capsule Over The Holidays

These are just some quick-and-dirty mirror selfies to give you guys an idea — as I mentioned already, almost everything I’m loving right now just went on sale, so time is of the essence.

1. The Everyday Outfit: MOTHER Ditcher Jeans + White Boots, Bag & Cropped Puffer Jacket

sweater (S) – 20% off | jacket (S petite) | jeans (26) – $100 off | bag – 30% off | boots (also at Nordstrom)

This is my new everyday look. I’ve lightened up everything — boots, jeans, coat, bag — yet this look is still perfectly functional and cozy. It literally doesn’t matter what sweater I wear. The MOTHER jeans are bananas soft (they run a little big too), and the Sorel boots are a style I’ve worn before — waterproof, warm and with seriously grippy soles.

jacket (S petite) | jeans (26) – $100 off | bag – 30% off

I’ve owned this shiny puffer coat from Athleta for several weeks now and really like it. It just needed a lighter bag and boots to pull the whole look together. I love the slightly snow-princess vibe.

The sweater is a boxy, almost-cropped cashmere sweater from Everlane. I’ve found that these shorter sweaters have been the key to successfully transitioning to a looser denim style, and this Everlane sweater is great: softer than Everlane’s previous cashmere sweaters and a little thicker too.

sweater (S) – 20% off | jeans (26) – $100 off | boots (also at Nordstrom)

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2. An Outfit For A Casual Night Out With Friends: MOTHER Ditcher Jeans + Sweater Vest

vest (S) – gift-card event | jeans (26) – $100 off | boots – 40% off (also at Nordstrom, full price)

This outfit is great for any activity where you’l get too hot: crowded restaurants or bars, house parties where you’re helping, etc. And the photo above really shows how soft and slouchy these MOTHER jeans are. I’m a huge fan.

Furthermore, this puffer jacket has been useful for two reasons: One, it’s cropped and looks good with looser denim styles. Two, it has a subtle shine, so it can vibe like a night-out jacket too.

vest (S) – gift-card event | jacket (S petite) | jeans (26) – $100 off | bag – 30% off | boots – 40% off (also at Nordstrom, full price)

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3. A Slightly Sexier Night-Out Outfit: Naadam Cashmere Sweater + Sarah Flint Heels

sweater (S) – 30% off (also at Naadam) | jeans (26) – $100 off | heels – $100 off purchase of 2 | similar necklace – 30% off | bag – 50% off

This Naadam sweater looks strange in the product shots, but it’s ahhhhh-mazing on. It’s cashmere — so warm and snuggly — but the cut is very, very sexy. Wear a pretty bra underneath, sometimes it peeks out.

sweater (S) – 30% off (also at Naadam) | jeans (26) – $100 off | heels – $100 off purchase of 2 | similar necklace – 30% off | bag – 50% off

And while the opportunities to wear heels like this in the winter are few and far between…I sometimes like to try during the holidays. And while I own Sarah Flint’s ridiculously comfortable (and sexy) heels in both nude and black…I think the sparkly gunmetal might be the best choice.

Lastly, nothing perks up a night-out outfit like a feather bag. I’ve had a tiny black one I’ve been getting compliments on for years…but this J.Crew purchase might be even better. It’s fancy yet fits EVERYTHING.

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4. One More Casual Holiday Party Outfit: Everlane Cashmere Sweater + Gap Barrel Jeans

sweater (S) – 20% off | GAP jeans (27P) – 40% off | heels – $100 off purchase of 2 | earrings – 50% off | bag – 50% off

So, first of all: JEANS. These are JUST as soft as the MOTHER Ditchers, but they’re Gap’s high-rise barrel jeans!! I finally ordered a pair after getting sick of hearing Amy, Laura and Em rave and rave and rave about them…and now I totally get the hype. I’m wearing size 4 petite, and I forgot how much I appreciate a good petite size range.

Once again, these are the Sarah Flint heels with the thick padding (even in the arch) and steel stiletto heel I can actually walk in. Can you mayyyybe see how the sparkly gunmetal would work with both of these outfits?

Also, J.Crew just killing it with holiday accessories. These teardrop earrings. Man. SO FUN.

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5. My Road-Trip Outfit: Suuuuper-Soft Gap Jeans, UGG Mini Boots + Black Sweater

sweater (S) – 20% off | Gap jeans (27P) – 40% off | UGG mini boots | sh*t that i knit hat – 25% off

A fresher choice would be UGG’s Ultra Mini boots, but I still have my regular old UGG Minis, so here they are. Still the only shoe I actually want to wear for hours in the car.

Once again, let me just reinforce: suuuuuper-soft jeans. Soft enough for eight hours in the car (literally just did this yesterday). And these hats are pretty special (and 25% off too).

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6. The Easiest Winter Outfit: Gap Barrel Jeans + GANNI Chelsea Boots

sweater (S) – 20% off | Gap jeans (27P) – 40% off | boots – 40% off (also at Nordstrom, full price)

This outfit shows why these leather GANNI Chelsea boots are so freaking useful: They’re amazing with cropped jeans. They’re also amazing with leggings (see here) and/or skinny jeans, making them one of the few boots that really do work with everything.

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7. A Warm & Cute Outfit For Walking Around: Gap Faux-Leather Pants + Sorel Boots

sweater (S) – 50% off | faux-leather pants (4P) – 40% off | bag – 30% off | boots (also at Nordstrom)

I don’t always love when shoes and bags perfectly match…but this year, I’m digging it. I also cannot recommend Gap’s faux-leather jeans enough. They’re lined in fleece and significantly warmer than my jeans. There’s nothing I’d rather wear for walking around outside in the cold.

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8. Take It Up a Notch: Jewel Tones + Black

sweater (S) – 50% off | faux-leather pants (4P) | boots – 40% off (also at Nordstrom, full price) |

Same outfit as above but with my GANNI Chelsea boots. I find that black can be a tricky color to pair with, well, uh…color, but dark, rich jewel tones (like emerald green and oxblood) look kiiiiind of amazing with black. Add in those big green J.Crew earrings, and I’d easily wear this (admittedly quirky) outfit out at night too.

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9. Winter Outfit, French-Girl Style: Stripes + Faux Leather

Ref sweater (S) – 25% off | faux-leather pants (4P) | boots – 40% off (also at Nordstrom, full price)

The genius part of Ref’s striped cashmere boyfriend sweater is that it looks just as good untucked as it does tucked in. Linzi and I both bought this sweater last winter (maybe even the winter before) and couldn’t be more thrilled that Reformation brought it back again. (In even more colors, but I still love the classic stripes.)

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10. When The Event’s More Cool Than Fancy: Faux Leather + Sweater Vest

vest (S) – gift card event | faux-leather pants (4P) | boots – 40% off (also at Nordstrom, full price)

If it’s freezing (or for daytime plans), I’ll wear the boots, as pictured. For night…maybe I’d try the heels. But in any case, the combo of cool-girl faux leather with a knit sweater vest is making me very happy.

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So, obviously there are many, many more outfit combinations I could make with this capsule wardrobe — this is just a quick list. But most of these pieces are on sale, and since I loved how this all came together…I had to share.

For some holiday joy, head to Holiday Central, our one-stop-shop for all the sparkle, sales and presents we have to offer. Browse gift ideas here, grab some holiday outfit inspo here, and shop all the best deals from Black Friday and Cyber Monday here.

Good luck out there!

xo,

S