Each of the 5 outfits here is built around a single Carhartt jacket: a brown hooded one, a tan one, a green one, a grey one, or a denim one with a corduroy collar, so the jacket already hanging in your closet tells you which look to copy.
Pair it with whatever sits closest on the palette: tan pants for the green, dark jeans and a belt for the grey, black pants and a striped button-down for the denim.
The denim jacket with the corduroy collar is the dressiest of the 5, and I’d call the grey look the plainest.
1. Brown Hooded Jacket
A brown hooded Carhartt worn open over a white tee is about as easy as streetwear gets. The jacket is the only loud piece, so everything under it should stay quiet.
Keep the tee plain and the pants dark, as here. A simple necklace is enough extra, and I would stop there.
Leave the jacket unzipped so the white shows. Closed, the outfit loses its contrast.
2. Tan Carhartt Jacket
Tan on top and tan on the feet, with light-wash denim between them, makes this a one-family color outfit. The white tee breaks it up so nothing blurs together.
Baggy jeans suit a boxy work jacket better than slim ones, since the proportions match. I prefer boots the same tone as the jacket; it reads deliberate rather than matched by accident.
The hood adds weight at the neck, so keep the tee simple.
3. Green Carhartt Jacket Outfit
If you already own tan pants, dark green is the Carhartt color that asks the least of you. Green and tan are both earth tones, so the outfit looks planned without effort.
Tan carpenter pants with brown boots keep the palette warm, and the white shirt underneath brightens the whole thing. I would pick this over black pants, which flatten the green.
It works well for a weekday errand run. Nothing here needs ironing.
4. Grey Carhartt Jacket Look
Faded grey asks for the plainest outfit you own: a white tee and dark blue jeans with a belt. The fade gives the jacket character, so the rest should not compete.
Dark denim against pale grey gives enough contrast without any extra pieces. Wear the jacket unzipped, as here, so the tee and belt show.
Grey is a quieter choice than brown or green. I like it for that.
5. Denim Carhartt Jacket with Corduroy Collar
A denim Carhartt with a brown corduroy collar looks dressier than most work jackets, mostly because the collar frames a shirt so well. The brown adds texture against the blue.
Under it, a striped button-down with black pants keeps the look sharp enough for an office that allows denim. Wear the shirt collar inside the corduroy one, not over it.
Black pants make the blue pop. Matching jeans would turn it into a denim-on-denim outfit.
Frequently Asked Questions
Are Carhartt jackets supposed to be baggy?
Yes, a Carhartt jacket is cut boxy and a little big, and your regular size gives you room to layer.
Under the jacket, stick to something plain like a white tee, so the Carhartt is the only thing asking for attention.
What kind of tops should I wear under a leather jacket?
Wear a simple T-shirt, a thin turtleneck, or a slim-fit shirt.
A white shirt looks fresh and classic, while a thin turtleneck in grey or black adds depth. All of these sit well with the jacket without competing with it.
