One Month Away: Crafting the Ultimate Winter Capsule Wardrobe for Travel

I have relatives in Italy, Canada, India, and Australia, so multiple times each year, I prepare a suitcase for extensive international journeys. As a regular traveler, I’ve refined my packing technique into a precise method over the last couple of decades, and as a style editor, I’ve also become increasingly selective with my essential wardrobe pieces. Therefore, I’ve developed a capsule wardrobe suitable for each season and travel occasion. Every piece is chic and comfortable, but the highlight is that I can combine them interchangeably, and they can all fit inside a single carry-on bag.

In just a few days, I will be departing for a month-long journey to northern Italy, and as I compose this, I have a fully-packed carry-on bag just a few feet away. It’s loaded with all the snug sweaters, comfortable footwear, and delightful outfits for holiday parties that I desire — with additional space for some gifts for my family. From a cashmere pullover (on sale during Nordstrom’s Half-yearly Sale) to the cozy pajamas from a brand loved by Oprah that I’m gifting to my sister to the comfy Good American jeans which my mother and I both swear by, this might just be my best-packed bag to date.

Caslon Cashmere Crewneck Sweater

I adore extremely soft sweaters, and I have experimented with a variety of cashmere and wool selections, but from the moment I first put on this 100 percent cashmere pullover — and at such a reasonable price — I realized I had no need to browse other labels. It feels so luxurious against my skin, pairs flawlessly with a range of bottoms, and can be layered over or under other articles on this list. I possess this in black, but I plan to acquire it in red since it will inject a splash of color into my winter collection and is currently available at more than half off in Nordstrom’s Half-yearly Sale.

Madewell Harlow Wide-leg Pants

There’s a genuine delight in feeling as though you’re donned in soft sweatpants when, in reality, you’re styling a chic pair of trousers — and I discovered that in the Lululemon City Sleek Utilitech Wide-leg Pants the very first time. Wide-leg trousers have become my preferred choice for flying and traveling days as they are spacious, comfortable, and flattering, while also presenting a polished appearance. Adaptable and simple to dress up or down, pair this all-season staple with a basic tee, sweater, or blazer for any endeavor on your travel agenda. While my preferred styles from Luluemon are currently unavailable, the T+L team is fond of a comparable version from Madewell — it’s the Harlow Wide-leg Pant.

Vivaia Amanda Water-repellant Booties

I refuse to allow my travel outfits to hinder my objective of achieving 10,000 steps each day, and for that reason, I exclusively wear comfortable shoes during my excursions to guarantee that I can remain on my feet all day without discomfort. I’ve been utilizing these Vivaia booties for years, I can walk in them for hours while living in New York City, and I consistently choose them when preparing for any chilly-weather escapade. Thanks to the flexible material, I can wear warm, thick socks with these boots in winter and light, breathable cotton socks in spring and autumn. I own the black version, but I’m planning to add the dark brown pair to my wish list (hint, hint, family).

Topshop Lace-trim Satin Midi Skirt

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I am an avid admirer of silk, as it appears elegant and can effortlessly enhance any attire — even when combined with a basic t-shirt or crewneck sweater. I also adore lace for the same reasons; thus, upon discovering this satin Topshop skirt featuring a lace edge, I realized it would be the ideal addition to my travel fashion collection. It integrates flawlessly with every top in my wardrobe (as well as with sneakers and boots), demonstrating its adaptability as I can mix and match it, allowing me to pack minimally, and it suits various occasions from family gatherings to nights out.

The Drop Kendra Button-up Shirt

I enjoy a crisp button-up, but what I particularly value about this selection is the slightly oversized silhouette and breathable 100 percent cotton material that lends it a comfortable and less formal appearance. I have it in white, and I love to tuck it into my Good American jeans, although I also wore it unbuttoned over a swimsuit as a cover-up during a beach vacation a few months back. I usually wear a medium, but I opted for a large since I desired a really loose fit. If you require additional sizes beyond what’s offered, take a look at this other highly-rated white button-down from Amazon priced at just $30.

Splendid Sivian Bouclé Coat

A cozy yet fashionable bouclé coat can transform even the most layered outfit during winter into something remarkably stylish. I receive compliments from strangers on the street nearly every time I don this piece in white, and the forgiving material doesn’t offer the same constrictive feel that some wool coats possess. I even wear this on airplanes, as it serves wonderfully as a makeshift blanket for long-haul flights. I pair it with a matching cashmere scarf, which is among the best gifts I’ve ever received.

The Drop Shelly V-neck Long-sleeve Maxi Dress

A timeless black dress is always a safe choice, and I particularly adore maxi dresses since they are suitable for all seasons. I’ve worn this over a swimsuit with sandals for a beach retreat in Capri, alongside loafers and a blazer for a fall journey to London, and recently paired it with maroon boots for Thanksgiving. While I naturally favor the black for its flexibility, this also comes in neon pink and vibrant lime, which would be stunning for spring or on a tropical escape.

Looking for more little black dresses? Consider this ruffled, wrap-front midi dress, this midi dress with a ruched top and tiered skirt, or this newly released ribbed, pleated, wrap midi dress — all highly rated and under $55.

Princess Polly Oswin Turtleneck Sweater

A few years back, I purchased this sweater on a whim, and it has since become one of the most frequently worn items in my wardrobe. Due to the incredibly soft, thick fabric, it serves as my go-to second layer for flights, and I even wear it to sleep if I find myself in a chilly hotel room while traveling. I will combine it with leggings or wide-leg pants for a flight and then dress it up with a mini skirt and tights for the office or while exploring a new city during vacation. While sizes are flying off the shelves, you can find similar styles like this
“`Madewell wool and alpaca oversized sweater (currently 40 percent discounted) or consider this classic 100 percent cotton turtleneck from J.Crew for under $100.

Good American Good Skate High-waisted Wide-leg Jeans

I will not sacrifice my comfort for fashion, so when I acquired these Good American jeans around four years ago, I understood I had discovered the ideal everyday pair — and one that would turn into a go-to for traveling. The material is elastic and pleasant, yet still manages to provide a defined silhouette, while the wide-leg design appears completely elegant when teamed with my favorite snug turtleneck and ankle boots. I praised them so much that my mother was persuaded to purchase a pair and even got rid of all her old jeans because they simply fell short by comparison.

Karl Lagerfeld Faux Leather Blazer

Winter presents a greater challenge in creating outfits than other seasons due to the numerous layers involved. This is why I have a few outfit formulas I rely on; one includes a blazer with a turtleneck, jeans, and ankle boots. Another is a blazer paired with a long-sleeved shirt, skirt, and knee-high boots. The constant? A blazer. The instant I donned this faux leather jacket, I realized it would be a crucial addition to my wardrobe. The soft, adaptable texture and slightly oversized shape allow it to be effortlessly dressed up or down, instantly making any outfit fashionable.

Sporty & Rich New York Health Club Sweatshirt

A multifunctional sweatshirt is the ultimate easily packable layer for traveling, as it can be combined with any bottoms and utilized for any event (depending on how you accessorize it). I’ve been eyeing this sweatshirt for months, and it appears my patience has paid off, as I received one as a Diwali gift. I adore it so much that I’ve incorporated it into my gym routine multiple times each week; however, I also intend to wear it with leggings during errands and trips, and I could effortlessly dress it up with jeans and trendy jewelry for a casual dinner with friends.

Cozy Earth Long-sleeve Pajama Set

Regardless of what I put on, comfort is paramount — and it holds even more significance when it pertains to pajamas. Although I once thought I couldn’t possibly spend over $50 on sleepwear, Oprah’s preferred lounge brand altered my perspective. I received one of Cozy Earth’s pajama sets as a gift, and I have completely converted, thanks to the incredibly soft bamboo viscose fabric that is somehow plush and breathable. Thank goodness it’s moisture-wicking as well, as I admit to being a sweaty sleeper.

Billy Reid Wool Turtleneck Contour Sweater Dress

There’s one item I cherish more than a little black dress, and that’s a turtlenecked little black dress. This one from Billy Reid is exceptional across all categories, from the luxurious and stretchy texture to the seductive slit detail. Yes, it’s quite expensive, but it serves as an exceptional investment piece or present — and right now, you can even score it for 50 percent off post-holidays. Trust that it will remain fashionable for years to come. I plan to sport this with some boots and chunky accessories for many of my upcoming holiday gatherings.

Skims Fits Everybody Thong

If you’ve been eager to test…Skims without investing in one of the more expensive bodysuits or lounge apparel items, grab this thong on sale before it eventually sells out. Crafted from a luxuriously soft material with a cotton-lined gusset, it feels like a second layer of skin without being overly tight or constrictive. I possess multiple pairs of these and am consistently searching for them in my lingerie drawer because they are the most pleasant underwear I own. They are also the sole items I wear on a long-haul journey since they nearly give the sensation of going commando. 

Stems Cotton Cashmere Socks

By now, you’re aware that I’m quite a fan of cashmere, but these socks surpassed my anticipations. They’re plush and stylish, and while they provide warmth, they’re also light enough that I frequently wear them to bed. They occupy such a minimal amount of space in my luggage, and since they’re so convenient to pack, I invariably place a pair in my tote bag to switch into once I board any extended flight.  

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