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When I think of an overshirt, the first thing that comes to mind is a heavy flannel shirt-jacket with a checked or tartan pattern. A flannel overshirt is the best option if you're looking for a cozy overshirt for fall.
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Wool will help retain heat even when it's wet. It's also incredibly durable. A good wool overshirt is likely to cost more than other types of overshirts as wool clothing is expensive to produce. Buy the highest quality wool shirt jacket you can afford to lower your cost per wear and save money in the long run.
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Military-inspired overshirts often feature flapped pockets, epaulets, and snaps on the cuffs. You can think of them almost as a pared-down field jacket. Military-inspired overshirts are most commonly found in cotton or canvas in solid colors such as navy, green, or a shade of brown.
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Denim is also twill-woven cotton fabric. Denim overshirts occupy the space between denim shirts and denim jackets. They usually are slightly longer than denim jackets (which should reach just below the belt). Denim overshirts usually have breast pockets. Dark blue denim overshirts are more formal than light washes.
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Casual and durable, corduroy is a fantastic fabric for overshirts. Corduroy, being a somewhat uncommon fabric, will help you stand out. Go for a brown corduroy shirt-jacket with double breast pockets for a classic option.
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Most overshirts have buttons. Occasionally, you can find an overshirt that has a zipper in the front. These overshirts usually lean more towards the jacket end of the spectrum.
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The ideal overshirt fit depends on how you plan on wearing it. For example, if you plan to wear your overshirt over a thick sweater, you should opt for a looser, slightly longer fit than if you intend to wear it over just a t-shirt.
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Overshirts should be long enough to cover your belt. You should be able to raise your hands above your head without exposing your midriff. The hem should extend no further than the bottom of the fly. You don't want to look like you're wearing a dress.
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When it comes to dressing well, fit is king. Make sure that the fit of your overshirt is intentional. Make sure it fits the way you'd like before purchasing, or make plans to take it to a tailor.
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One of the best things about cold weather is that you can comfortably wear more layers than in warmer months. That said, you can wear too many layers. Generally, three layers look better than two layers.
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Overshirts are not made to be tucked in. They should always be worn untucked.
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Many overshirts can be worn like a regular casual collared shirt. Denim, military-inspired, and flannel overshirts are best for this. Wear a red flannel overshirt with navy chinos. Throw on a pair of brown leather chukkas and a matching belt.
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An unbuttoned overshirt worn over top of a t-shirt is a great relaxed look for a relaxed evening by the campfire. Consider wearing a classic white crew neck tee underneath a dark blue wool overshirt. Pair with gray-wash jeans and black leather sneakers.
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Another option is to wear a cable knit sweater underneath a shirt jacket with a zipper. You might go with a gray sweater underneath a dark green shirt jacket. Dark blue jeans and oxblood brogues will help to elevate this look.
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Overshirts were originally a garment worn by men that work with their hands. When choosing an overshirt for manual labor, you'll want to choose a cut that is somewhat looser than you'd probably wear for casual social situations. Look for a shirt-jacket with large pockets,
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The key is to understand layering. An overshirt is an excellent middle layer when dressing for winter. For truly frigid conditions, you could pull on a warm synthetic base layer, then a crewneck pullover sweater, followed by an overshirt, and finally, an overcoat.