
Take your Caesar salad game to new heights with this winter twist that packs bold flavors and amazing textures. Tough kale and thin-sliced Brussels sprouts create the base for hot, oven-roasted squash, while a zesty Greek yogurt dressing and spicy Dijon breadcrumbs add rich layers that make each mouthful better than the one before. After lots of kitchen trials, I've found that what really makes this salad stand out is how each part is carefully handled.
I've played around with tons of winter veggies and dressing options, and I've learned that giving each component proper attention turns basic ingredients into something really special.
Key Ingredient Guide
- Kale: Go for Tuscan (Lacinato) kale with rich green, strong leaves. Skip any that look yellow or droopy. You want leaves that feel tough but can still bend
- Brussels Sprouts: Pick ones that are firm, tightly packed and bright green. The smaller ones usually taste sweeter and work better when uncooked
- Squash: Butternut squash is your best bet for its sturdy texture and natural sweetness. Look for ones with dull, tan skin without any mushy parts
Step-By-Step Cooking Guide
- Vegetable Preparation:
- Pull kale leaves off the tough stems. Stack them up and cut into thin strips. Cut the ends off Brussels sprouts. Slice them super thin. Skin the squash and cut into even cubes. Make sure all pieces are about the same size. Put each veggie in separate bowls.
- Creating the Perfect Dressing:
- Use yogurt that isn't cold from the fridge. Stir yogurt till it's smooth as silk. Mix in garlic and anchovy paste bit by bit. Pour in lemon juice and add Dijon. Slowly add olive oil while mixing. Toss in Parmesan at the end. Add fresh black pepper. Let sit for at least 30 minutes.
- Roasting the Squash:
- Get your oven hot at 425°F. Mix squash with olive oil. Sprinkle with smoked paprika. Add a bit of oregano and chili powder. Lay out on a baking tray. Don't crowd the pieces. Cook until edges turn golden. Flip them halfway.
- Dijon Breadcrumb Development:
- Warm up olive oil in a pan. Toss in minced garlic until you can smell it. Add some Dijon mustard. Mix with breadcrumbs. Cook until they turn golden. Keep stirring so they don't burn. Add salt and pepper while hot. Cool them down fully.

When I was younger, winter salads were just boring side dishes until I figured out how to make them the star. My mom always showed me that spending time with each ingredient, especially rubbing the kale thoroughly, totally changes the end result.
Mastering Different Textures
What makes a winter salad truly fantastic is mixing different mouthfeels. The soft, hot squash works beautifully against the snappy Brussels sprouts, while those breadcrumbs bring that much-needed crispy element.
Hot Meets Cold Magic
When warm squash touches the raw greens, it softens them just a bit where they meet, creating cool spots and warmer areas throughout your bowl. This means you'll get something slightly different with each bite.

I now bring this salad to all my winter gatherings, showing everyone that salads can be filling and fancy at once. There's something magical about how the squash sends up that lovely smell when it hits the cool greens, and how those Dijon breadcrumbs add their savory snap. It really shows off how winter produce can come together into something you won't forget.
Frequently Asked Questions
- → Can I prep it early?
- Totally! Make dressing, roast squash, and prep croutons a day ahead. Assemble everything fresh when you're ready to serve.
- → How can I make it vegetarian?
- Skip anchovies in the dressing, and toss in soy sauce or capers for depth. It'll taste awesome either way!
- → What's the trick to tender kale?
- Drizzle olive oil on the kale, then use your hands to squeeze and rub the leaves gently for a minute or two. It helps soften them up!
- → Can I use another veggie?
- Totally fine! Swap out butternut squash for acorn squash or diced sweet potato. Just make sure the pieces are similar in size for even cooking.
- → How long does dressing last?
- Stored in the fridge, the dressing keeps well for 3-4 days. Stir again before drizzling.