Traveling Light: Packing List for a Winter Weekend in Louisville, Kentucky

Revealing everything I packed for a freezing cold winter weekend in Louisville.

For a moment, I hesitated to include the phrase “Traveling Light” in the title of this post, because frigid temps in Louisville called for way more garments and accessories than I would usually pack for a weekend – but I managed to pack everything in my carry-on and personal item all the same.

(I do want to express my gratitude, though – initially the low for this trip was 3°F/-16°C, but mercifully, the coldest it got was 9°F/-13°C. Brr!).

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With that forecast in mind, what’s fashionable more or less went right out the window and I focused on feeling comfortable and warm when packing for my weekend away – and I suggest you do the same, no matter the destination.

Looking for more packing list inspiration? Discover what's in my suitcase each season: Spring | Summer | Fall | Winter

It hasn’t really been that cold here in Charlotte this season, so I looked to past winter trips for guidance on what to pack for Louisville in the winter. Heading to my closet, I pulled cozy cashmere sweaters, my favorite winter accessories, and breathable wool base layers. I’ve written before about how Southerners love our A/C in the summer, but you know what? We love our heat in the winter just as much (if not more!), and I knew I’d need to balance my outfits for indoor and outdoor wear.

When it’s that cold outside, I reach for a down jacket. I have a love/hate relationship with my big puffy coat: I love that it keeps me warm and toasty even when the weather is abysmal (I also love that I snagged it for $30 on Poshmark), but I hate having to wear it. I saw my chance for one fleeting travel day to avoid wearing my monster of a puffer and I shamelessly took it. Thankfully it compresses down and I can pack it in my carry-on with no problem. With two coats, I knew I would only be able to comfortably pack one pair of shoes, so I landed on a comfortable pair of black lug-sole boots.

Ready to see everything I picked?

LOUISVILLE WINTER PACKING LIST

Grey Cashmere Sweater* | Black Cashmere Sweater* | Wool Blazer* | Midi Dress | Blue Denim | Cargo Pants℅ | Wool Trousers℅ | Puffer Coat | Wool Coat℅ | Turtleneck Base Layer | Crew Neck Base Layer℅ | Wool Leggings℅ | Belt | Gloves* | Scarf | Sunglasses | Beret | Beanie* | Waterproof Boots℅ | Convertible Bag℅

LOUISVILLE OUTFITS

Saturday

In all honesty, I could have gone without my blue jeans and camel coat for this trip – but I added them in anyway for a little dose of seasonal normalcy. My look for the early hours of my visit to Louisville isn’t groundbreaking, but there’s a lot of value in wearing a throw-on-and-go outfit for an early morning flight.

The best part of this outfit is the piece that’s slightly hidden – tucking my wool blazer (linked to the current fabric offering) under my coat adds an extra layer of warmth without adding bulk. And once I’ve shed my outer layer indoors, it makes for a lovely third piece.

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A collage of the garments worn on Saturday night featuring a grey midi dress, camel coat, and black innerwear — Turtleneck Base Layer | Beret | Midi Dress | Wool Coat℅ | Wool Leggings℅ | Convertible Bag℅ | Wool Blazer* | Belt | Gloves* | Waterproof Boots℅ | Scarf

Saturday Evening

Louisville has no shortage of white tablecloth restaurants with a strict dress code – but thankfully we skirted around them all. Still, I saw an opportunity to dress up for our lovely dinner at Mayan Cafe and seized it – but in my own way. I knew we’d be walking twenty minutes in the freezing cold, so I layered up with soft merino wool close to my skin with a pair of leggings and a sheer turtleneck before popping a cotton knit dress over my head. Black accessories broke up the beige quite nicely, and I topped everything off with my wool beret – because why not?

A sudden snowfall on our walk back made for the most pleasant ending to our evening, and by morning, all of the clothing we’d strung about our hotel room had dried completely (that’s the magic of wool!).

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A collage of all items worn on a cold day in Louisville, including wool innerwear and a puffy coat — Crew Neck Base Layer℅ | Black Cashmere Sweater* | Wool Leggings℅ | Cargo Pants℅ | Puffer Coat | Wool Blazer*| Scarf | Convertible Bag℅ | Waterproof Boots℅ | Beanie* | Gloves* | Sunglasses

Sunday

Brr… Sunday was the coldest day of our trip – the temperatures had not yet reached the teens by the time we headed out the door for brunch. I layered up with my wool base layers again and wore all-black for a little extra warmth (including my cargo pants – aren’t these the fanciest cargo pants you’ve ever seen?). I may have been wearing four tops and two bottoms at once, but prioritizing thin layers and natural fibers meant I never felt like the Michelin Man. Well, until I added my big ol’ puffer, which I begrudgingly wore and was immensely grateful to have on the icy Derby track and along the windy riverfront.

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Monday

Our bittersweet last day in Louisville! As you can tell from the little bit of snow stuck to the ground, it was still below freezing. We spent the bulk of the day indoors, enjoying our last meals and bourbon cocktails before paying a visit to the Louisville Slugger Museum. Though the shoes have changed, you may recognize this outfit from last year’s winter trip to NYC. I’m a big believer in outfit repeating – if you love an outfit, you should wear it!

*This item is no longer available and a similar product is linked

WRAPPING UP: FINAL THOUGHTS ON PACKING FOR LOUISVILLE IN THE WINTER

Two surprise snowfalls were a really wonderful cherry on top of our trip – and I am so grateful that I chose to pack a pair of waterproof boots (save 20% with code WAYWARDBLOG20) for the journey! I felt safe and relatively comfortable with the items I packed in my suitcase, and outfit-wise, I felt like the looks I chose meshed with what the locals were wearing. I think everyone’s priority for this cold winter weekend was just staying warm – and I’m on board with that.

One unexpected assist for the weekend was our rental car; with so many accessories in play at any given moment, I relied heavily on the vehicle to act as a traveling closet, shedding and adding layers as needed.

I know this packing list is a far cry from the sundresses and big, bold hats seen at Derby, but of course, that only comes once a year! Perhaps my next visit to Louisville will fall during a warmer month, and I can share a better glimpse at the city’s personal style. But until then, pass me another bourbon on the rocks!

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Questions for you

Would you rather pack for a cold weather trip or a warm weather trip?

If you could only bring one pair of shoes on a winter getaway, which pair would you reach for?