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Illustration for article titled How to Dress Like a Shipster
Style GirlfriendStyle Girlfriend is the go-to destination for guys seeking not just fashion advice, but lifestyle tips, tricks, and shortcuts - all from a friendly, female editorial team’s perspective. Each week, Team SG will round up the clothes, grooming products and more men need to live their most stylish lives.

The folks over at Esquire UK recently decreed 2020 the year of the “shipster,” a terrible personal style portmanteau combining fisherman with hipster.

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Despite the awful name, they’re right on the money about this already cresting men’s fashion trend. This year, expect to see rugged layers, stompy boots and tiny beanies borrowed from The Life Aquatic with Steve Zissou’s wardrobe department dominating the Instagram feeds of menswear bloggers and airport paparazzi pictures of dressed-down male celebs alike.

And...your closet? Because here’s the thing. Yes, the name is dumb, but, well, it’s not a terrible look?! I mean, leave the fishing net and dog-eared copy of Infinite Jest at home, and you can probably pull it off without looking like you’re “trying a trend.” Below, check out some picks for nailing the Shipster vibe this year:

ASOS mini fisherman beanie in black, $18
Best Made Co. Lambswool Cap of Courage (which, lol ok), $48
ASOS mini fisherman beanie in black, $18
Best Made Co. Lambswool Cap of Courage (which, lol ok), $48
Graphic: Ana Luisa Suarez

Knit beanies in dark shades like black or navy look right at home on a shipster’s head. So do styles in a super-pigmented “my crew will spot me if I fall overboard” hue like tomato red or highway cone orange.

In terms of how long one can wear a hat like this into the year, I generally give the following guidelines: if it’s cold enough for a jacket (even a light one!), you can get away with wearing a beanie. Once the weather warms up, though, switch to a hat that’s not intended to be a sweater for your head.

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A shipster’s sweater should look sturdy yet home-made. Think: a wooly number knitted for you by your first true love, whom you cruelly abandoned to set sail for adventure on the high seas, or dumped after college to move to Bushwick with your buddies.

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Obviously a shipster requires trousers that will keep him warm on cold nights on the water, or for walking home after a late-night show by a band you’ve never heard of (but he’s seen a hundred times).

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Corduroy’s a good bet for winter, while a sturdy twill can take over in the spring.

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No one outside of a military zone needs combat boots, but I have to admit the style (for both men and women) has grown on me in the last year or so. Wear yours with your warm pants now, and with jeans well into the warm weather months.

Roll or cuff the bottoms to show off the boots’ lacing for a nice l’il shipster show-off style move.

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You’re going to need an extra-thick sock to go under those boots; a camp sock is just the thing. They feel serious and look cool without resorting to a basic crew sock.

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The trendy chore coat has become a year-round staple, thanks to extra-heavy fabrics like flannel linings and shearling collars. Wear yours over literally all of the above to complete your shipster OOTD.


Megan Collins started Style Girlfriend to help guys look and feel their best. Today, she and her team share tips, tricks, and shortcuts to a closet that inspires confidence.

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