
Take your regular Caesar salad up a notch with this rich winter twist. Tough kale and thin-sliced Brussels sprouts work great with hot, roasted squash chunks, while a tangy yogurt dressing and spicy Dijon breadcrumbs make every mouthful more exciting than you'd expect. I've tried this dozens of times and found that giving each part special attention really makes this dish stand out.
I've played around with many winter veggies and dressing options and found that putting care into each part turns basic ingredients into something you won't forget.
Key Ingredients Breakdown
- Kale: Go for Tuscan (Lacinato) kale with rich green, strong leaves. Stay away from yellow or floppy bits. You want leaves that are tough but bendable
- Brussels Sprouts: Look for firm, bright green sprouts that feel heavy for their size. The little ones taste sweeter and work better raw
- Squash: Butternut squash is your best bet for its sturdy bite and natural sweetness. Pick one with dull, tan skin and no squishy parts
Step-by-Step Cooking Guide
- Getting Veggies Ready:
- Pull kale leaves off the tough stems. Stack them up and cut into thin strips. Cut off Brussels sprout bottoms. Slice them super thin. Skin the squash and cut into same-sized cubes. Keep all veggies in separate bowls.
- Whipping Up Your Dressing:
- Use yogurt that isn't cold from the fridge. Beat yogurt till it's silky smooth. Mix in garlic and anchovy paste bit by bit. Add lemon juice and Dijon. Pour olive oil in slowly while stirring. Mix in Parmesan at the end. Crack some black pepper on top. Let it sit for at least 30 minutes.
- Cooking the Squash:
- Heat your oven to 425°F. Coat squash with olive oil. Sprinkle with smoked paprika. Add some oregano and chili powder. Lay pieces out on a baking sheet. Don't crowd them. Cook till edges turn golden. Flip them halfway.
- Making Tasty Breadcrumbs:
- Warm olive oil in a pan. Cook minced garlic till you can smell it. Add some Dijon mustard. Mix with breadcrumbs. Cook till they turn golden brown. Keep stirring so they don't burn. Add salt and pepper while hot. Let them cool all the way.

When I was little, winter salads were just boring side dishes until I figured out how to make them amazing. Mom always told me that spending time with each ingredient, especially rubbing the kale properly, changes everything.
Balancing Different Textures
What makes a winter salad really good is mixing different textures. The soft, roasted squash feels completely different from the crunchy sprouts, and the breadcrumbs give that essential crispy element.
Playing With Hot And Cold
When warm squash touches the raw greens, it softens them just a bit where they meet, creating spots with different feels throughout your bowl. This means you'll get something slightly different with each bite.

This has turned into my go-to dish when friends come over in winter, showing that salads can be filling and fancy. The smell of hot squash hitting the fresh greens, the way those Dijon breadcrumbs add their savory crunch – it shows just how good winter veggies can be when you treat them right.
Frequently Asked Questions
- → Can I prep this early?
- Yes! Roast the squash, mix the dressing, and make croutons a day before. Just combine everything right before serving.
- → What about a vegetarian option?
- Of course! Skip anchovy paste and replace it with a little soy sauce or capers for a similar flavorful punch.
- → How do I soften kale properly?
- Pour olive oil on chopped leaves, then gently massage for a minute or two. It'll soften the texture and enhance tenderness.
- → Can another squash work?
- Sure! Try acorn squash or sweet potato instead. Just cut them evenly to make cooking simple.
- → What’s the shelf life of the dressing?
- It stays fresh in the fridge for 3-4 days. Just give it a good mix before using.