Before the dawn of a new season, I like to reevaluate an area of my apartment very near and dear to my heart: my shoe closet. I take stock of all the shoes that are continuing to serve me well, get rid of the few that have reached the end of their lifetime, and take note of which pairs I want to add to my collection next.

Now that the cold weather is settling in, I’ve compiled a list of the five key shoes that will define my winter wardrobe. Spend a few minutes on Instagram or any street style site, and you’ll see that these pairs are seasonal must-haves. Steve Madden has an excellent selection of all five styles, which I’ll be shopping at Zappos (my go-to footwear retailer). These styles are just one click away from your shoe closet, and here’s everything you need to know about them.

It’s collectively agreed that flats were the biggest shoe trend of 2023, and I don’t foresee the craze slowing down anytime soon. Now that fashion people have gotten a taste of this comfortable, chic footwear style, it’s safe to say no one is going back. From traditional Mary Janes to shiny metallic iterations, flats are an easy way to add a stylish detail to your wardrobe basics.

Though sneakers are a year-round fashion item for many, I reach for them the most the second the temperature drops. Their comfort and practicality make them a no-brainer for braving the cold weather, and I can rely on them to get me through a full day of activities in any city. They add a cool touch to any cozy sweater-and-denim ensemble.

Boots obviously make the winter wardrobe cut—I can’t imagine dressing for this time of year without them. I could go back and forth for hours debating which styles are the best, but you really can’t go wrong. I’ll be wearing taller boots—both flat and heeled—with all my favorite dresses (and tights when necessary!) and Chelsea boots with more low-key denim looks. Steve Madden has them all.

Finding the right balance between a comfortable and fashion-forward heel is, in fact, possible. Anything below three inches is typically a safe bet, and a little kitten heel never fails to make a statement. During the cold months, I tend to pull them out for fun nights on the town, and with holiday party season finally here, I’ll be styling them with my dressier outfits too. Some of the on-trend options I’m eyeing this year are red slingback heels and ballet-inspired mesh pumps.

Loafers have a way of making any outfit feel more put-together. Whether I’m wearing them to work or on the weekends, I love the polished school-girl vibe they offer any outfit. I recommend styling them with tailored separates for a chic daytime ensemble or with a miniskirt, leather jacket, and tights for an evening look. Bonus points for adding cute ankle socks.