What to Wear in 66 Degree Weather?

March 23, 2025

Dressing for 66-degree weather can feel like walking a fine line between too warm and too cool.

It’s not quite hot enough for just a T-shirt, but wearing a heavy jacket might leave you sweating by midday.

So, how do you strike the perfect balance?

Understanding 66-Degree Weather

At 66 degrees, the weather is mild, but it’s not so warm that you can get away with wearing just a t-shirt and shorts.

Likewise, it's not cold enough to justify a heavy jacket or winter coat. The goal is to strike a balance between comfort, breathability, and warmth.

Layering is your best friend in these situations, as it allows you to adapt to changing conditions throughout the day.

Best Tops for 66-Degree Weather

Lightweight Layers

When dressing for 66-degree weather, lightweight layers are key. A casual long-sleeve shirt or a thin sweater will provide just enough warmth without making you feel too hot.

Opt for breathable fabrics like cotton, linen, or lightweight wool that allow air circulation while still keeping you cozy.

A well-fitting crew neck sweater is a solid option if you want something versatile that can go with a variety of bottoms. For a more relaxed vibe, you could go for a flannel shirt or a lightweight button-down.

These options allow you to open a button or roll up your sleeves when the sun shines and provide enough coverage when the weather cools down.

Casual Jackets and Outerwear

Since 66-degree weather can sometimes be breezy, you may want to bring a lightweight jacket along. A denim jacket, bomber jacket, or a windbreaker can add an extra layer of protection without making you feel weighed down.

These pieces are perfect for transitioning from cooler mornings to warmer afternoons. If you prefer a more structured look, opt for a blazer made from lightweight cotton or linen.

Another great option is a casual zip-up jacket or a cardigan that you can easily take off if it gets too warm. The benefit of these layers is that they’re easy to pack away when not needed, but they still provide that extra bit of coverage when the temperature dips.

Best Bottoms for 66-Degree Weather

Jeans and Chinos

Jeans are a classic choice for 66-degree weather because they offer a perfect middle ground between comfort and style. Choose a pair of slim or straight-leg jeans made from medium-weight denim.

These will be breathable enough to wear during the day while still offering protection against the chillier temperatures in the morning or evening. Light to medium washes work well, especially if you're aiming for a more relaxed look.

Chinos are another excellent option for this temperature. Chinos come in a variety of cuts and colors, so you can easily find a pair that matches your personal style.

A slim-fit chino in a neutral color like beige, khaki, or navy will provide a polished look without feeling too heavy. Chinos are also versatile enough to pair with either casual shoes or sneakers.

Shorts (When to Wear Them)

Though it’s a bit borderline, there are some moments when wearing shorts is an acceptable choice for 66-degree weather.

If you’re in an area where the weather tends to be sunny and dry, you can consider wearing tailored shorts or casual athletic shorts. Pair them with sneakers or loafers for a laid-back look.

However, be mindful of the time of day. Early mornings or late evenings might feel too chilly for shorts, but during peak daylight hours, you’ll feel comfortable enough. If you’re not sure whether to go with shorts, it’s better to err on the side of caution and opt for a longer pair of pants.

Footwear for 66-Degree Weather

Sneakers and Casual Shoes

Footwear is a crucial element in completing your outfit for 66-degree weather. Since it’s not too hot or too cold, sneakers or casual shoes are perfect. A pair of clean, well-maintained sneakers can provide both comfort and style, making them suitable for nearly every occasion.

If you’re looking to dress up your look a bit, loafers or brogues are great choices. These shoes can be worn with both jeans and chinos, adding a touch of sophistication without feeling out of place.

Choose leather or suede options for a slightly more refined appearance, while canvas loafers can maintain a more relaxed vibe.

Boots for Extra Warmth

If you find yourself in a cooler region or the weather takes a sudden turn for the chillier, consider adding a pair of boots to your outfit. Chelsea boots or desert boots made from lightweight materials can give you the added warmth you need without overheating.

A pair of leather boots will complement both chinos and denim, especially if you’re going for a more rugged or stylish look.

What to Avoid in 66-Degree Weather

Heavy Outerwear and Excessive Layers

It’s important to avoid wearing heavy coats, thick sweaters, or excessive layers that could cause you to overheat as the day warms up. In this moderate temperature, layering smartly is key. Stick to breathable materials that will allow you to adjust your outfit as needed.

Winter Shoes and Boots

Avoid winter-specific shoes and boots that are made from heavy leather or thick, insulating materials. These footwear options are designed for colder conditions and will likely make your feet feel too warm in 66-degree weather.