Do you want to dress like Sam and Dean Winchester from the TV series Supernatural? Welcome to our style guide that provides you with the best clothing to wear to match the rugged outdoorsman look of your favorite monster hunting brothers.

The television show Supernatural features the two brothers, Sam and Dean Winchester, driving around the United States investigating paranormal activities, fighting monsters and wooing women. They are in their own way a kind of gentlemen adventurers, as they seek adventure and seduce women at taverns across their fictional world. Many of the early season episodes featured a ‘monster of the week’ format, with the two brothers basically inserted into cliché monster movies and who then proceed to change the outcome of the tale with their heroic efforts before driving off into the sunset in their 1967 Chevrolet Impala to save another town from disaster.

More importantly the style of fashion that Dean and Sam Winchester wear in the television show is very popular among the female audience of the show. Indeed there is a huge audience of women that like to watch Supernatural because they are attracted to the rugged and handsome style of these monster hunting brothers. So if you can imitate this look yourself you might find that you can attract women who enjoy watching this television show. They might not be able to date the stars of the TV show but they can date the next best thing — You.

For a man that is looking for a down-to-earth fashion style adopting the trademark look of the Supernatural stars is an easy and affordable choice.

How to Dress like Sam and Dean Winchester

While both brothers have very similar looks, there are some unique clothing choices between the two of them.

Dean and Sam Winchester have a rugged, handsome look for a man that is down to earth.
Dean and Sam Winchester have a rugged, handsome look for a man that is down to earth.

The Winchester brothers are portrayed as working class men, who wear iconic clothing such as you would see among blue collar workers, in particular those who work outdoors such as loggers. This is a very casual dress style but still very clean and neat. As a man cannot always be expected to wear his finest suits and needs clothing to wear in his daily life you cannot go wrong adopting some of the style choices that Sam and Dean Winchester select. This is especially the case if you live in a rural area or intend to date country girls.

How to Dress Like Dean Winchester

Dean Winchester Style Shirts

Dean Winchester frequently wears a solid black t-shirt with a Dickies work shirt, unbuttoned and sometimes with the sleeves rolled up to just below his elbows. Dean will also wear Carhartt and Henly branded shirts, too. Sometimes these are single colored work shirts, and other times they have a flannel pattern.

For the t-shirts, we recommend American Apparel short sleeve crew cut shirts.

You don’t necessarily need to wear the exact same brand of shirts. There are many producers who make similar style of work shirts, such as Wrangler.

Dean will also wear a military style canvas jacket as well as sometimes a brown leather jacket. This military style jacket by WenVen is similar to the one Dean wears and this brow leather jacket by Blingsoul is similar to the leather jacket Dean wore in many early episodes. There is also a third, slightly more expensive brown leather jacket here too.

Dean Winchester in his leather jacket.
Dean Winchester in his leather jacket.

Dean Winchester Style Pants

Dean wears Lucky brand 361 vintage straight jeans. Lucky brand jeans are high quality. You can also wear Diesel branded jeans, too. Both of these are straight jeans, and are not a baggy style of leg.

Dean Winchester style boots

There are several kinds of boots Dean wears during the Supernatural television series. The most common boots he wears in episodes are Carhartt leather logger boots.

There are some additional boots I am recommending to you that can also go along with this style of clothing, even if they are not expressly identical to what Dean Winchester wears in the show. I am a fan of Don’s Footwear bespoke boots, which are available as elevator shoes with a midsole that adds a few extra inches to your height when worn. As I am a man on the shorter side of the scale I find that having elevator shoes and height increasing boots helps me keep up with women that wear heels, which many of the women I date like to do. The bespoke boots produced by Don’s Footwear are some of the highest class elevator boots available on the market and the design allows a man to walk normally with no awkwardness as with many other kinds of “height increasing boots”, which are designed more like a woman’s high heels than shoes. These boots from Don’s workshop have a solid, flat sole with no arch and are designed to hide their platform in the design of the shoe itself. Most people will have no idea you are wearing elevator shoes with these on. I personally own a pair of the St. George II Extended shaft boots featured below, and I am very pleased with them.

Naturally if you are going to wear boots you should have good, comfortable socks. Carhartt makes some of the best boots socks in my opinion and I recommend them.

How to Dress Like Sam Winchester

Sam Winchester Style Shirts

Sam Winchester tends to wear plaid flannel shirts more often than his brother Dean does.

The Supernatural stars frequently wear plaid long sleeved shirts, often with the sleeves rolled up.
The Supernatural stars frequently wear plaid long sleeved shirts, often with the sleeves rolled up.

Occasionally, Sam also wears buttoned down dress shirts as a means of showing his more reserved nature compared to his brother Dean.

Sam Winchester Style Jacket

Sam often likes to wear a Carhartt Men’s Sandstone Active Jacket, as well as a suede collared flannel lined jacket. In the later seasons he also wears a quilt lined Yukon style coat.

Sam Winchester Style Pants

Just as with his brother Dean Winchester, Sam also wears Lucky and Diesel brand denim jeans.

Sam Winchester Style Boots

Unlike Dean, Sam typically wears slip on outdoor boots from the Australian bootmaker Blundstone. These are a very modern style of men’s boot that fits Sam’s personality as the more technical member of the duo.

Don’s Footwear also produces a slip on leather boot that utilizes their unique height increasing sole technology. If you are a shorter man such as myself you may find it a good idea to invest into some bespoke boots produced for you by Don’s Footwear.

Sam and Dean Winchester Accessories

The Winchester brothers are known for wearing military style wrist watches. One of these is the Suunto military style sportswatch.

Now if your primary goal in reading this guide is just to dress up in a costume, these accessories may be useful for you. You can get a replica of Dean’s amulet necklace as well as a replica of his stainless steel ring he wears on his right hand.

Do you have any suggestions for additional accessories and clothing that should be included on this list? Let us here at The Millennial Gentleman know in the comments below.


Carey Martell is Editor in Chief for The Millennial Gentleman. A thirty something modern man who is politically independent, non-religious but a firm believer in ideals of chivalry and traditional family values. Carey lives his life as a vagabond digital nomad traveling and living life to the fullest while managing his businesses remotely with a laptop and internet hotspot connection.