A Carry-On Packing List for Milwaukee, Wisconsin

Opening up my suitcase to share my real-life packing list for a Spring weekend in Milwaukee, Wisconsin

Last month, Michael and I flew North to Milwaukee for my birthday. Despite seemingly everyone’s hesitations, I found an energetic city full of great food, cool art, and ample opportunity to simply get out and explore on foot.

I was beyond excited for the trip – but not excited to pack for it.

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You see, thanks to the inconsistent weather forecast, I wound up having to pack for three seasons’ worth of Milwaukee weather in as many days. The first day saw summery weather: sunny with a high of 72°F. The second day brought chilly April showers (the kind that makes you just want to stay indoors and take a nap). And the third and final day? Snow.

Yes, friends, it snowed.

Just forty-eight hours after wearing a tank top, I found myself bundled up in a parka.

Thankfully the weather forecast predicted this aggressive weather shift, so I pulled the elements I would need from my wardrobe to properly prepare: thin layers, natural fibers, and weatherproof shoes and outerwear. Though I was slightly annoyed at having to pull my heavy coat and boots out of the closet, I knew I’d be glad I did. As for the rest of my Milwaukee wardrobe? I reached for a darker color palette to cover any potentially wet or muddy spots.

Looking for more packing content? Check out my packing lists by season: Spring | Summer | Fall | Winter

As airfare continues to rise, I’ve embraced budget airline travel out of necessity – and those carriers generally only permit travelers to carry just a personal item for free (you can check out my packing lists for Chicago, New York, and Austin to see some recent examples). We flew American Airlines this time around, and not only did it feel downright luxurious to travel with my carry-on suitcase, but it also felt simply necessary.

This was also my first chance to fly with my Knack Pack℅, as it is more generously sized than the budget carriers’ allowances; though I didn’t end up needing it, I liked having the freedom of expanding the backpack to fit any fun souvenirs.

With these two incredibly efficient bags, I wound up with plenty of extra room in my luggage (even with a big puffy parka stuffed inside!). As tempting as it is to throw extra items in “just in case,” I like to exercise restraint when possible to make getting dressed a little easier. Without further ado, here’s everything I packed, a blurb about why I chose each item, a roundup of outfit photos, and some general packing tips for Milwaukee:

MILWAUKEE PACKING LIST

WHY I CHOSE THESE ITEMS FOR MILWAUKEE

Tops

Silk Tank | I bought this silk V-neck tank back in 2019, but only lately has it started getting significant mileage. It’s a little sultry thanks to a deep V in the back, but still completely wearable for every situation. As it’s a soft and shiny silk, I only wear it when the temperature is below 80°F to avoid sweating in it.

Striped Tee* | A wardrobe staple, and one of the easiest patterns to wear. Stripes are great for making a simple t-shirt feel a little less basic.

Wool Turtleneck* | I’ll sing the praises of Merino wool forever: It’s warm! It’s soft! It doesn’t smell! This one is extra cozy while remaining thin enough to tuck seamlessly.

Cashmere Sweater℅ | I wore this all fall and winter long, so it was easy to grab it for this trip, too.

Alpaca Cardigan | Alpaca is another favorite fabric – it’s extra lightweight and warm.

Dresses

Sweatshirt Dress* | This thrift find is cozy but feels a little fancier thanks to the ruffle shoulder. I embrace the tension, especially when paired with chunky boots.

Bottoms

Straight Leg Denim* | An easygoing pair of jeans with lots of stretch. If you’re having trouble breaking away from skinny jeans, straight-leg denim is a good place to start.

Wide Leg Pants* | Fitted through the hips and bum, these wide-leg pants don’t feel sloppy or baggy – which means they dress up and down with ease, like a wardrobe chameleon.

Outerwear

Rain Jacket | This jacket is lightweight and keeps me toasty and dry. It’s great for when the temps start to dip but it’s not yet cold enough for a parka.

Parka | Yes, that coat. I was reluctant to pack it for this trip because I just didn’t want it to be cold enough to need it. But I don’t control the weather, and I was so grateful to have it.

Accessories

Crossbody Bag* | This bag makes an appearance on so many packing lists because it’s just the right size. It may not be “on trend” but it’s a travel workhorse.

Scarf | This scarf is luxuriously soft and warm, and it fits into one of the zippered pockets on my coat (meaning I can always have it on hand!).

Beret* | Don’t get me wrong – I love a beanie. But sometimes you just want to chic it up, you know?

Leather Belt | This belt looks far more expensive than it is, thanks to its tonal buckle. Best of all, it doesn’t seem to aggravate the metal detectors at the airport.

Gloves* | I like to keep a pair in every coat pocket – and these leather tech gloves kept my fingers toasty while pulling up the city map on my phone.

Sunglasses | This pair is my current go-to, thanks to their lightweight frame and lifetime warranty (perfect for the rough nature of travel!).

Shoes

Sneakers | I don’t do this often, but I wound up purchasing this pair on this trip. The temperatures were higher than predicted, and I was dying in my boots (I guess that’s a testament to how warm the boots are?). They were fine for this trip, but I’m not quite sure if I love them. In retrospect, I should have just tossed in a pair of my Everlane sneakers with all the extra room in my bag.

Lug Sole Boots℅ | These boots are my go-to when the temperatures drop. They’re sturdy and warm – and get this – they’re weatherproof. I was so grateful to have these at the ready when the rain and snow started.

Not Pictured

Underwear + Innerwear | I packed more than enough underwear for this trip, as well as some of my favorite ultra-thin inner layers: a Merino turtleneck, a light tank, and warm leggings.

Hosiery | New for me this year is a pair of fleece-lined tights that are supposed to look like sheer tights over bare legs. They are surprisingly warm, but I’m not sure they’re quite convincing anyone that those are my legs… I also popped on a pair of compression socks for the flight and tossed in wool socks for warmth.

Toiletries + Makeup | Lately I’ve been flying with this dopp kit, and I’m so impressed at how well it holds all the little things like hair ties, nail clippers, a lint roller, cotton swabs, and more.

Technology | I decided to leave my laptop at home on this trip, figuring I could just use my phone for all my tech needs, and that was wise. But in addition to my phone and wall charger, I packed my AirPods, portable wireless charger, and trusty digital camera.

Jewelry | I kept things ultra-simple, relying on my favorite gold chains, bands, and stud earrings.

MILWAUKEE OUTFITS

Alyssa walks in front of the Milwaukee Art Museum wearing a tan sweater — Alpaca Cardigan | Sunglasses | Crossbody Bag*

Alyssa studies a painting at the Milwaukee Art Museum — Cashmere Sweater℅ | Straight Leg Denim* | Rain Jacket | Crossbody Bag*

Alyssa wears a grey sweater and black pants in Milwaukee — Wool Turtleneck* | Wide Leg Pants* | Lug Sole Boots℅ | Crossbody Bag*

Alyssa wears a black dress with black boots and a beret — Sweatshirt Dress* | Fleece-Lined Tights | Lug Sole Boots℅ | Crossbody Bag* | Beret* | Parka

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

MY THOUGHTS ON PACKING FOR MILWAUKEE

How I’d rate my packing list

I’m going to be honest (well, like always): I didn’t fully love all of these outfits. They’re fine, don’t get me wrong – I just felt a little less than stylish thanks to the weather. Digging deeper, I’m sure my feelings about this are largely based on just feeling over winter weather. The burden of toting a big coat (although I’m grateful that it fit in my suitcase for the inbound flight), the struggle to put on so many layers, the general icky icy dampness – it’s fun for a while, but by April I’m ready to emerge from my cashmere cocoon.

Another thing that bothered me for this trip was having to purchase those sneakers in the middle, just to wear for the first of the three days. I kicked myself for having to take the time (and money!) out of my travel itinerary and put it toward something I already have at home. With the blessing of a larger suitcase, I should have just tossed them in. Even though I don’t like the idea of packing extra things “just in case,” this would have been helpful.

How I typically “rate” my packing list isn’t on a numbered scale, but by a feeling of having just the right amount of clothing and how comfortable I felt at the destination: this one may not have been my best.

General packing tips for Milwaukee

Midwestern style is very casual – I saw lots of baseball caps and logo tees. And as the temperatures dropped, I quickly learned that Midwesterners are cut from a different cloth. My tender, thin-blooded Southern self had to fully bundle in my long underwear, sweaters, scarf, and coat just to make a four-block walk. As for the locals? I saw multiple people in shorts in sub-50°F weather – and even one person wearing them in the snow.

So, if I had to share my top tip for packing for Milwaukee (or any other destination in the region), it’s this: Pack for the forecast but know your comfort levels. After all, what feels “cold” to this Florida-born gal might just be your shorts-and-a-tee ideal day.

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Questions for you

What is something you’ve had to buy in the middle of a trip?

Do you prefer to pack for warm weather or cold weather?

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Traveling Light: A Spring Packing List for Milwaukee, Wisconsin