The second grid is where the jackets get more varied: hooded, chore, canvas and denim. If the Detroit is the sharp one, these are the easy ones. I reach for them on days when I just want to put something on and leave.

 

Carhartt says the Active Jac was introduced in 1975 and is still its top-selling jacket, which tells you something about how many people want a hood and a simple shape. Here it shows up as the OG Active Jacket, the OG Active jacket (winter) and the OG Active hooded jacket. The Active Cotton Stone Canvas Drawstring Hooded Jacket is the canvas one with a drawstring hood, and the Hooded Painter jacket and Hooded Nelson jacket are the other hooded options.

 

Now the Chore Coat, which is my favorite shape in this group. Carhartt's archive holds ads for the Chore Coat dating back to 1917, and the company says the coat is largely unchanged today. That is a long run for a pocketed, boxy coat. Try the Pocket Chore Coat and the OG Chore corduroy-collar coat as the Carhartt coat women reach for over a dress, or open over a tee and trousers. The OG Michigan logo-patch coat and the Tan OG Michigan Jacket sit in the same family. The Clark jacket and Brown Clark Jacket are the plainer ones, and I would try them over tailoring.

 

For denim, the Off-white Mercer Stripe Denim Chore Jacket is the one I keep thinking about, because it puts a stripe on the chore shape. The Black Belmar Denim Jacket and Navy Belmar Denim Jacket are the plainer options, and the OG hooded zip-up denim jacket is the casual one. Tuck the sleeves up once and see if the cuff hits your wrist bone.

The third grid is for colder days: a fleece, two bombers, quilted pieces and a few padded jackets. I will be plain about this group. These are the shapes I would add after I already own a Detroit or a chore coat, not before.

 

The Arcan bomber jacket and the logo-patch bomber jacket are the classic bomber shape, and they sit shorter than a coat, so they look good with a long skirt or wide-leg trousers. The Elliot fleece pouch-pocket jacket is the soft one, and I would wear it where a sweatshirt feels too thin and a coat feels too much. The two quilted ripstop jackets have a quilted line that looks tidy over a knit.

 

For padding, look at the Stanwood padded logo-patch jacket, the Stanwood insulated jacket and the Toronto puffer jacket. The names tell you these are padded or insulated, but I would not read a number into that, since nothing on the page gives one. Try them on with the sweater you actually wear in winter, and check that you can lift your arms over your head without the hem riding up.

 

Carhartt describes duck as a tightly woven cotton fabric known for durability and resistance to wear. It says firm duck has a structured feel that breaks in naturally over time, so the fabric fits the wearer, while washed duck is pre-washed for a softer feel and does not need the break-in. Duck is usually the stiffest fabric at first. That is worth knowing before you decide how stiff you want it.

 

What I would skip: buying a padded jacket in a size that only works over a thin shirt. Try it over the heaviest thing you will wear under it, and skip anything that pulls across your back when you reach forward.

Here is how I would choose. Start with the shape you will wear most. If you live in jeans and boots, the Detroit jacket is the easiest. If you want something roomier for layering, go with the chore coat. If you want a hood, the Active shape is the one, and if it is properly cold, move to the bombers and padded styles.

 

Then do a fitting-room test. Raise your arms, cross them, and reach forward. Check where the hem lands: a Detroit should sit near your waistband, a chore coat a little lower. Look at the sleeve, and see whether it covers your wrist bone when your arm is bent.

 

Finally, decide how much break-in you want. Firm duck starts stiff and softens as you wear it, and washed duck starts soft. Either way, a workwear jacket looks best when it looks lived in, and I would take one that fits me well on day one over one I have to grow into. If you want to keep browsing, I also put together Bomber Jackets and Designer Bomber Jackets.