It’s the season for layering! As we transition into cooler weather, it’s not yet chilly enough for a heavy coat, but staying warm is essential. When temperatures settle in the 50s, selecting your outfit can become quite challenging.

You may find yourself wondering: Are boots too warm for today? Should I wear a hat? Will it get warmer later? Am I going to be hopping in and out of the car, or will I be strolling through the city? These are important questions to consider.

I usually start my outfit selection with an outer layer, deciding which jacket to wear. A leather jacket, trench coat, or a light wool peacoat are all fantastic options that remain timeless.

Beneath the outer layer, a knitted item is a solid choice—whether you opt for cashmere or cotton will depend on your budget and comfort level, as preferences can vary widely. Then, you’ll need to choose between a crew neck, v-neck, or cardigan, as it’s still too early for turtlenecks.

You can also add another layer beneath the knit, such as a tank top, t-shirt, or blouse, based on how warm or cold you tend to feel.

Next, decide between jeans or slacks, depending on the vibe you want—casual or dressy.

Finally, consider your footwear: if you’re wearing a leather jacket with a light knit and an underlayer, boots will provide the necessary warmth. However, if you choose a blouse with a heavier knit and a wool peacoat, loafers or sneakers will be just fine.

Here are some great examples of outfits to wear now!