• Start Here
  • Shop

The Heddels Overshirt Guide 2022

As we snap into fall, it’s time to talk overshirts. Perhaps the quintessential fall garment, the overshirt is your best bud when the temperature drops and will still be by your side through the depths of winter. Easy to layer over or under, take on and off, and good lookin’ with almost any clothing combo, it’s a no-brainer to invest in a high-quality overshirt or two that you’ll use for many years to come.

A category too broad and too important to whittle down to just six pieces in our Five Plus One format, we’ve put together a list of what we think are the best overshirts on the market this season, breaking them down into three categories — straight hem, round hem, and under $200. We’ve also featured a range of fabrics to ensure that readers in different climates are covered, so, make yourself a coffee and prepare to pour over a list of the best overshirts in the game.

Straight Hem

ts(s) Mixed Color Cotton Round Flap Pocket Baggy Shirt

The-Heddels-Overshirt-Guide-2022 Available for $295 from Namu Shop

Kicking off our selection of straight-hemmed overshirts is the Mixed Color Cotton Round Flap Pocket Baggy Shirt from ts(s). That’s a mouthful, for sure, but as usual with ts(s), this overshirt is a piece of understated glory. Buttonless flap pockets are a lesser-seen pocket type on shirting and usually reserved for jackets, but they really set this otherwise simple piece off, which is made from a 100% cotton medium-weight twill that looks to have been brushed for texture. 

The Round Flap Baggy Shirt comes in two colorways — gray and khaki — both finished with a short point collar, adjustable cuffs, shell buttons, and spit hem. Dress this one up with a fine knit sweater underneath and some formal trousers, or go completely casual with the same kind of styling exhibited by Namu above.

Available for $295 from Namu Shop

Benzak Denim Developers BWS-03 Military Overshirt


Benzak‘s BWS-03 Military Overshirt in 11oz Indigo x Indigo Herringbone Twill is one of the more classic naval style overshirts you’ll find on this list. When we think of overshirts in the American heritage vein, the USN Officer’s shirt comes to mind, and this one’s a great example. It’s pretty close to a true reproduction, but it’s obviously updated in fit, fabric, and details to suit the modern (hoodie-wearing) soldier’s needs.

With a nice light 11oz. Collect Mills double indigo Herringbone Twill fabric, the Military Overshirt comes equipped with Mil-spec melamine buttons throughout, two roomy chest pockets (wouldn’t be an Officer’s shirt without ’em), adjustable cuffs, and tonal Benzak longhorn bull logo embroidery.

BWS-03 11 oz. Indigo x Indigo twill, available for $235 from Division Road


This article is part of our paid membership program, Heddels+ that includes:

  • Up to 20% discounts at select brands and retailers
  • 2+ exclusive articles per week
  • 2+ product giveaways per month
  • No ads on Heddels.com
  • Keeping our mission at Heddels alive
$1 a week trial, $10/month after.

Join today and gain instant access to:

2 product giveaways per month
Exclusive Heddels+ articles and podcast episodes
Heddels+ Discord community
No ads on the entire Heddels site
Up to 20% off at the Heddels Shop, STAG Provisions, Blue in Green, Clutch Cafe, and more!