The winter holidays: candy and cookies abound at work, the kitchen table gets covered in gift wrapping supplies, and everyone and their Grandmother travels across the country. 2014 is actually the first Christmas I’ll be hosting my family, rather than traveling to see them – when N and I bought our house, we campaigned for the opportunity, and now we’re neck-deep in Christmas lights and meal planning. Still, this will be the first Christmas I’ve slept in my own bed since 2007 (when I lived in the same town as my mom), so I’m something of a professional at packing for holiday travel. Here are some of the key things I’ve learned:

1. Keep your color palette compatible. Make sure that all tops could pair with each bottom, all shoes and bags are in the same family, and so forth. If you’re bringing a pair of brown pumps, make all your neutrals brown-friendly. By ensuring every piece has versatility among the others, you’re guaranteed not to have to over-pack.
2. Similarly, don’t pack duplicates. You absolutely, definitely, surely do not need more than a single pair of pumps. There’s no reason to bring more than one clutch purse. If you’re packing a blazer, don’t pack two blazers.
3. Now is the time to use those samples. As a lover of cosmetic goods, I’m usually flush with single-use samples of face cream, shampoo, etc. Here is where they come in handy! Don’t bother packing a full-size mascara when a trial tube will do.
4. Simplicity is key. Comfortable and simple pieces will always look chic, no matter the occasion. Just make sure they are flattering, too – yoga pants belong in the gym, please.
5. Underpack. It’s likely you’re going to be receiving gifts, after all.
6. Wear your boots on the airplane! Don’t waste space in a suitcase on a massive pair of boots.
7. Don’t forget the essential items: toothbrush, pajamas, and more underpants than you think you’ll need.

When I’d travel to my mom’s for the holidays, I was typically gone five days – three days at home, with a day of travel on either end. For such a trip, here’s how I’d pack:

Jeans: Madewell | Tops: Athleta [L to R: 1, 2, 3, 4] | Dresses: Madewell [L to R: 1, 2] | Earrings: Gorjana | Necklace: Stella & Dot | Ring: Melinda Maria | Boots: Naturalizer

Denim: Have we discussed Madewell jeans? We need to discuss Madewell jeans. They are the ONLY jeans that do for my lower half what I always hope from a pair of jeans. They also stretch enough to be comfortable but not so much that they sag. They’re also the exact perfect rise – not high enough to look like you belong on Saved by the Bell, but not so low you’re tugging at the waist every five minutes. I have this pair of jeans – Skinny Skinny – in a number of colors. Every pair is my favorite. I would bring a single pair of jeans, unless you’re staying longer than a week.

Tops: Athleta has, hands down, the most reliable travel tops – I picked these four because they’re neutral but interesting, and loose enough to be forgiving after a huge family dinner. Bring enough tops to wear at least 3/4 of the days that you’re traveling.

Dresses: Sometimes, jeans aren’t quite dressy enough. That said, you don’t want to be traveling with easily-wrinkled woven fabrics. Enter the sweater dress. It’s fancy enough for Christmas Eve services at your parents’ church, but comfy enough to wear on the airplane if you so choose. Two of these will suffice, in case you’ve already worn one and another more-than-jeans opportunity arises.

Shoes: I’ve only included boots in this packing trip because I’d like to keep the packing light. Cognac boots will go with each of these pieces. Want a second pair of shoes in your suitcase? If you’re flying south, I recommend ballet flats (these are my favorite); if you’re headed north, oxfords.

Jewelry: I’m not a huge wearer of jewelry, and that philosophy has served me well while traveling. I like to bring a single, versatile piece of each type – earrings, necklace, ring. You can wear them all together, or wear them separately. These stud earrings are small and discreet, but catch the light well. The statement ring looks great when you’re a little dressed up. And this long pendant necklace will add flair to any of the above outfits.

Not pictured, but also encouraged: leggings and tights (for this suitcase, I’d pack charcoal gray), camis (nude-to-you and white), two bras (don’t ever wear the same bra two days in a row, people!), belt (in the same cognac color as the boots), and more pair of undies than days you’ll be gone (you might not wear them all, but better to have too many and not use them than the alternative).

And what am I packing it all in?

L to R: “Catalina,” Lo & Sons, “Tall Leather Tote,” Cuyana

A trip of this kind needs only two bags: one for your luggage, and one for your carry-on materials. This Lo & Sons weekender is a perfect travel bag, with the separate zip compartment for your shoes and plenty of space for everything else. This Cuyana tote is massive but polished, and can hold your Kindle, iPad, a scarf, magazines, snacks, and anything else you might need on-hand during your flight.

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Where are you going this winter, #PetiteCrew? What essentials are you packing?