How to Wear an Overshirt This Fall: 4 Ways That Work, and 4 to Buy

The overshirt is the layer that solves the awkward weeks of fall. It is too heavy to be a shirt and too light to be a coat, which is exactly why it works. It goes over a tee on Saturday, over a knit on Monday and under a coat in November. This is how to wear one, and four we would look at.

01. Over a plain tee, as the main event

Start here. Wear it open or buttoned over a white or grey tee, with straight jeans and boots. The overshirt is the outfit's main event, so pick a pattern or a strong solid and keep everything else quiet. Taylor Stitch's Cutter is a good example: an oversized 12.5-oz organic cotton twill in a check, with a chambray-lined collar and cuffs.

The mistake: buying it too big. The Cutter is cut oversized, so size down if you want shoulder seams that sit where they should. The hem should end around your hip, not your thigh.

02. Buttoned up, as the office layer

Here is the work-style angle. Skip the tee and wear a soft overshirt as a top layer over a shirt or a fine knit, with chinos and leather shoes. Mack Weldon's ACE Overshirt is a French terry, the same fabric as the brand's hoodies, cut like a shirt. It looks tidy, and it is comfortable. For a full smart-casual uniform, see our guide to business casual for men and the work capsule wardrobe.

The mistake: treating a knit like a jacket. A French terry overshirt is soft and drapes, so do not expect it to hold a sharp line. Keep the rest of the outfit simple.

03. In a solid colour, with earth tones

Dark green, navy and brown are the safest overshirt colours. Taylor Stitch's Maritime Shirt Jacket in Dark Forest is a 13-oz organic cotton moleskin twill with two oversized flap pockets. Wear it with cream chinos or dark denim and brown boots. It sits next to the workwear-inspired pieces in our 90s style trends for fall.

The mistake: matching the overshirt to your trousers. Dark green over olive chinos disappears. Contrast wins.

04. In wool, as the one you keep

If you want a single overshirt to last, buy wool. Filson's Jac-Shirt is 100% wool, in a tight weave that the brand says balances breathability with wind resistance. In navy it works with almost everything and it belongs in the same family as the heavier layers in our leather jackets guide.

The mistake: ignoring care. Wool should be brushed and aired, not washed after every wear.

Fit rules that apply to all of them

• Shoulders: the seam sits on the edge of your shoulder or slightly past it, not halfway down the arm.
• Length: the hem lands between your belt and mid-zip. A longer overshirt shortens your legs.
• Sleeves: the cuff ends at the wrist bone. Roll them once or twice for a relaxed look.
• Collar: wear it flat, not popped.

When the weather turns wet, the next layer up is a waxed coat, like the Barbour Burghley wax jacket that J. Press just brought back.

How to start

Buy one solid navy or dark green overshirt first. If your budget is around $170, Mack Weldon's ACE or a Taylor Stitch overshirt works; for a lifetime piece, the Filson wool is the investment. Then compare it with the other outerwear on our style page, and check the menswear topic for more. If you want a warmer piece, see Filson's insulated Cruiser in our Filson Spokane deal.

M&S also sells a pure cotton twill overshirt for about $79: see it in our Marks & Spencer outfit guide.