Best dressed for the Holidays!

Holiday travel season is here. Whether you’re jetting off to a festive destination, heading to the mountains, or taking a cozy road trip to visit family, you’ll find a variety of options to keep you warm, comfortable and chic while getting to where you need to be.

It’s also packed with detailed notes on some of the best travel essentials, perfect for active travelers or anyone on your gift list. It's a gifting goldmine!

Happy Holidays!

Jill

Clothing

54 Items

Some items I link may earn a small commission, which supports my business!

shopbop.com »
  • Jill D. on Dec 12, 2024

    I don't travel without my White and Warren travel wrap. From the plane to day to evening. So cozy and chic.

farfetch.com »
  • Jill D. on Dec 12, 2024

    Must haves!

bananarepublic.gap.com »
  • Jill D. on Dec 12, 2024

    This warm sweater dress is so versatile to wear with tights and boots in day to heels or tall boots at night. Love the cuff detail! Also comes in black and cream.

everlane.com »
revolve.com »
  • Jill D. on Dec 12, 2024

    Have to have a cool cap for the "I am not doing my hair" day.

nordstrom.com »
  • Jill D. on Dec 12, 2024

    Dress it up!

nordstrom.com »
  • Jill D. on Dec 12, 2024

    Stuart Weitzman always comfortable and stylish. Timeless.

net-a-porter.com »
  • Jill D. on Dec 12, 2024

    Your Bougie bag with EVERYTHING day and night.

jcrew.com »
  • Jill D. on Dec 12, 2024

    !!!

jcrew.com »
  • Jill D. on Dec 12, 2024

    The sheer sock trend is real and keeps your ankles warm-ish in your loafers.

quince.com »
  • Jill D. on Dec 12, 2024

    This cashmere lounge pant comes in beautiful fall colors. Hanging around the fire or off for coffee with sneakers or snow boots,

modaoperandi.com »
  • Jill D. on Dec 10, 2024

    Faux fur is everywhere - there are options from cropped to long. I love this for evening, and I also enjoy a long fur moment with jeans and a sweater and sneakers - it feels very model off duty.

jcrew.com »
  • Jill D. on Dec 12, 2024

    Don't forget you basic t-shirt layer.

target.com »
  • Jill D. on Dec 12, 2024

    Get you tights and hosiery at Target. Great options.

revolve.com »
  • Jill D. on Dec 10, 2024

    Favorite daughter really caught my eye with this style, I love the sweater sleeves, and the ivory boucle. If you already have a lot of coats in your wardrobe, consider adding ivory - especially if you have other cream pieces in your wardrobe - cream coats always remind me of Cameron Diaz in The Holiday - a look I always love.

net-a-porter.com »
  • Jill D. on Dec 12, 2024

    The "it" Citizens for Humanity jeans. Also in blue denim.

neimanmarcus.com »
  • Jill D. on Dec 12, 2024

    Ear cuffs. Your ears want to be noticed too.

net-a-porter.com »
shopbop.com »
  • Jill D. on Dec 12, 2024

    Always chic and cool layer with sweaters.

shopbop.com »
shop.mango.com »
  • Jill D. on Dec 10, 2024

    A tailored coat is always in style, this affordable option from Mango makes adding to cart very easy!

cuyana.com »
  • Jill D. on Dec 12, 2024

    Airplane chic an beyond.

leset.com »
  • Jill D. on Dec 12, 2024

    Love this dressed up off the shoulder top and so easy to pack.

bananarepublic.gap.com »
bergdorfgoodman.com »
shopbop.com »
  • Jill D. on Dec 12, 2024

    Great for layering.

jcrew.com »
  • Jill D. on Dec 12, 2024

    Alos in Burgundy.

jennikayne.com »
bergdorfgoodman.com »
  • Jill D. on Dec 10, 2024

    Mocha and all shades of brown are super popular this fall/winter, and Mocha mousse is the color for 2025 - so now is the perfect time to add a brown layer to your looks. You can wear this with black, gray, navy, burgundy, and cream

net-a-porter.com »
jcrew.com »
fwrd.com »
gap.com »
shopbop.com »
  • Jill D. on Dec 12, 2024

    cozy!

freepeople.com »
  • Jill D. on Dec 10, 2024

    A packable poncho from free people - great for anyone who is active, or wants a more casual layer this winter.

shopbop.com »
  • Jill D. on Dec 12, 2024

    Can't get enough of the New Balance 327. This basic combo will go with everything.

jcrew.com »
bergdorfgoodman.com »
  • Jill D. on Dec 12, 2024

    Boots, heels or sneakers. Your "go to" travel jean.

neimanmarcus.com »
shopbop.com »
bergdorfgoodman.com »
revolve.com »
  • Jill D. on Dec 12, 2024

    Basic hoop!

perfectmoment.com »
  • Jill D. on Dec 10, 2024

    A cropped puffer is always cute -this jacket will serve you well during cold weather activities, while also looking fashionable.

saksfifthavenue.com »
shop.lululemon.com »
bergdorfgoodman.com »
shop.lululemon.com »
jcrew.com »
landsend.com »
  • Jill D. on Dec 10, 2024

    available in plus

saksfifthavenue.com »
gap.com »
freepeople.com »
  • Jill D. on Dec 9, 2024

    Fashion forward packable puffer from Free People available in multiple colors

landsend.com »
  • Jill D. on Dec 9, 2024

    Lands End packable puffer available in petite, regular, tall and plus

quince.com »
  • Jill D. on Dec 9, 2024

    Packable puffer from Quince, comes in a variety of colors

Travel Essentials

33 Items

Some items I link may earn a small commission, which supports my business!

bergdorfgoodman.com »
  • Jill D. on Dec 9, 2024

    Carry on in a fun color

quince.com »
  • Jill D. on Dec 9, 2024

    Affordable travel set from Quince

awaytravel.com »
  • Jill D. on Dec 9, 2024

    Away: comes in multiple colors - perfect for when you need to check a bag

awaytravel.com »
  • Jill D. on Dec 9, 2024

    Away: for the carry on packer

cuyana.com »
  • Jill D. on Dec 9, 2024

    take this matching set from cuyana ( available in more colors) and take your carry on and personal item to a more fashionable level

cuyana.com »
  • Jill D. on Dec 10, 2024

    Perfect weekend tote, or for a carry on

cuyana.com »
  • Jill D. on Dec 9, 2024

    Make up case for at home, and for travel ( comes in a variety of colors)

cuyana.com »
  • Jill D. on Dec 10, 2024

    coordinating luggage tag

awaytravel.com »
  • Jill D. on Dec 9, 2024

    Away backpack : comes in other colors

quince.com »
  • Jill D. on Dec 10, 2024

    A chic quilted backpack for casual travel

awaytravel.com »
  • Jill D. on Dec 9, 2024

    Garment bag for special care items

awaytravel.com »
  • Jill D. on Dec 9, 2024

    packing cubes to organize your looks

revolve.com »
  • Jill D. on Dec 9, 2024

    Catch extra sleep on a flight in this festive mask

revolve.com »
  • Jill D. on Dec 10, 2024

    silk neck pillow

dickssportinggoods.com »
  • Jill D. on Dec 10, 2024

    Stay hydrated in this seasons hit color

neimanmarcus.com »
  • Jill D. on Dec 10, 2024

    A water bottle for the fashion girl

target.com »
  • Jill D. on Dec 10, 2024

    Stream your favorite podcast or show with high quality audio while traveling

target.com »
  • Jill D. on Dec 10, 2024

    We all need two sets of airpods, one for our home and one for on the go

target.com »
  • Jill D. on Dec 9, 2024

    travel charger

target.com »
  • Jill D. on Dec 9, 2024

    No more lost luggage

macys.com »
  • Jill D. on Dec 9, 2024

    travel steamer, so you can refresh your clothes on the go

revolve.com »
  • Jill D. on Dec 9, 2024

    for your fashion emergencies!

revolve.com »
  • Jill D. on Dec 10, 2024

    Winter is the season of dry skin, so make sure you have this lip balm in your make up case

revolve.com »
  • Jill D. on Dec 9, 2024

    No more dry winter skin with this handcream in your bag

sephora.com »
  • Jill D. on Dec 9, 2024

    Take this lotion stone through TSA no problem, super hydrating too!

bergdorfgoodman.com »
  • Jill D. on Dec 10, 2024

    Fun passport case

cuyana.com »
  • Jill D. on Dec 9, 2024

    Passport case

sephora.com »
  • Jill D. on Dec 9, 2024

    Luxury travel tolietry set from Sephora

sephora.com »
  • Jill D. on Dec 9, 2024

    Refresh your skin mid flight with these soothing facial spray

sephora.com »
  • Jill D. on Dec 9, 2024

    Viral jet lag mask, refresh your skin post travel with this hydrating mask

sephora.com »
  • Jill D. on Dec 10, 2024

    Clean hands on the go in a chic package and pleasant scent.

target.com »
  • Jill D. on Dec 9, 2024

    travel tolietry kit from Target

target.com »
  • Jill D. on Dec 10, 2024

    For wiping down your seat, and tray table

Travel Looks for Every Destination

8 Looks

Weekend Escape: When traveling with just a carry-on, every piece needs to pull double (or triple) duty. This coat works as both an activewear layer and a versatile style piece you can mix and match effortlessly. Pair the cashmere t-shirt with a sequin or satin skirt for a chic evening look, style the cropped pants with a festive sweater for cozy gatherings, and let the boots tie it all together—they go with everything.

Sunshine Retreat: This look effortlessly takes you from plane to dinner while keeping a festive touch with darker accents. Each piece is a versatile wardrobe staple: the trench layers beautifully over all your outfits, the white button-up pairs seamlessly with trousers or a fun skirt, and the jeans complement everything else in your carry-on. These timeless investments will elevate your travel wardrobe for years to come. And don’t forget the travel wrap—a stylist favorite that doubles as a cozy scarf and blanket for those chilly plane or car rides

Mountain Escape: This patent leather puffer is the ultimate layering piece, adding warmth and a bold statement to all your winter looks. The fleece-lined leggings are a travel essential—perfect for staying cozy on the go, tackling winter activities, or lounging in style. Elevate your après-ski wardrobe by pairing the updated Fair Isle sweater with classic denim for daytime or a satin maxi skirt for an effortlessly chic evening look.

Heading to the City: Showcase a little more edge with your look while keeping it elevated. Soften darker layers with cream accessories for contrast, and let this coat seamlessly transition from cocktail attire to casual city outings. The versatile ankle boots are a wardrobe powerhouse, pairing effortlessly with pants, skirts, denim, and more.

Long Haul Flight: This faux shearling coat is your ultimate winter companion, keeping you warm and stylish whether you’re strolling through a Christmas market or exploring winter cities like London and Paris. Stay cozy on the plane in a cashmere set, and repurpose the sweater with denim for effortless sightseeing looks. Chic and versatile for all your winter adventures.

Tropical Getaway: A packable winter coat is a must-have for everyday life and a game-changer for warm-weather travel. These silk pants are effortlessly chic—pair them with a tank and sandals when you arrive, or wear them for a comfortable travel look. Layer with a cashmere sweater for the journey, which also doubles as the perfect layer over summer dresses or skirts on cooler evenings.

Plane to Party: Holiday travel often calls for quick turnarounds—sometimes there’s no time to change or even unpack. This look is both chic and comfortable, perfect for a flight and whatever comes after. Let the coat double as a statement piece, and channel a model-off-duty vibe with a t-shirt and denim. The cashmere dress transitions effortlessly, styled casually with flat boots or loafers for a polished yet relaxed look.

Winter Road Trip: When it’s cold outside, staying cozy is key—especially on a long drive. This luxurious matching set from LESET is perfect for ultimate comfort. Layer with a warm cardigan to stay snug during the journey (and for those gas station or charging stops). Once you arrive, swap the cardigan for a chic coat to elevate your look. A simple hairpin and necklace complete the ensemble, keeping your hair effortlessly styled without a hair tie in sight.