Remember that Dean’s clothing comes from an era where clothes fitted the body closely, following the human form and hugging it. Nothing baggy, loose or tent-like should be used when trying to achieve the James Dean look.
If you want a truly authentic look, add cuffs to the leg ends of the jeans or simply turn them up. If that isn’t something you’re keen to wear, simply ensure that the ends are neat and not frayed. Most of James Dean’s jeans were in the mid to dark blue range, with some wear but still neat. Add a large belt with an obvious belt buckle to complete the look.
White t-shirts: It never hurts to have a number of these in the wardrobe, freshly laundered and pressed, ready for wearing. The white tee is very versatile too – it looks good under jackets (especially the leather kind) and by itself. Muscle cut polo shirts: Obviously, to show off the muscle work and generally look rebellious and cool.
If you’re going for a movie look, Rebel Without a Cause and East of Eden are worth watching as those demonstrate his greatest movie outfits. Rebel Without a Cause, he sported a red cotton windbreaker jacket, which you can buy on Dean’s official website, a white V-neck muscle cut shirt, and worn dark jeans, with very simple black engineer boots. East of Eden was his “good boy look”, he wore a khaki colored v-neck sweater, under it a white or light blue polo shirt, khaki slacks or pants, with brown dress shoes, or gray converse Chuck Taylor’s.
Work boots: Some classic black boots, which are plain and unadorned are the ideal choice. Pair these with plain white socks. If there’s a heel on them, so much the better. Simple converse shoes or similar for casual wear are fine. Again, pair with very basic, plain socks.
When wearing the jacket, have the collar flipped “up” (pop it), if you have to take it off, hang it over your shoulder. As noted earlier, Dean also wore a rebellious red jacket in Rebel without a cause, which gives a bit of variety to your wardrobe.
The swept back look can be done in varying degrees of severity, so let your hairdresser help you choose what is best for your needs. If you do have a pompadour, always have a comb; when your hair looks good, you’ll feel good, and when a sexy girl passes by, comb the side of your hair. Back in the 50’s, men told women they were sexy through combing their hair near them, or when they passed by.
When at a casual dress occasion, he usually sported a wool sports jacket, in the brown or khaki colors, a white or cream colored button down shirt, thin brown belt, khaki pants, and brown dress shoes – never wear square toe shoes, always round. The long overcoat worn in this image was also a Dean trademark. It’s a great addition for the colder weather.
Shrug off the rudeness of others. It’s not worth your while to chase compliments or confirm people’s nastiness by stooping to their level. Stand up for yourself. Dean didn’t like violence; he was tough but not rough. Use your smarts and your wit to maneuver around the violent people you come across and don’t be a bully.