20+ Rainy Day Outfits for Men That’ll Still Impress

Rainy day outfits for men get their real test at the door. You step inside, push the hood back, and what’s underneath either looks planned or looks like you swam there. Luckily, rain asks for far fewer changes than most guys pack for.

I picked 20+ fits from Pinterest for you, from trail shells and nylon pants to long coats under a black umbrella. Each one is sorted by the piece that keeps the water out. Keep one layer waterproof, and everything under it can stay exactly the way you like it.

How to Dress for Rain Without Looking Like a Hiker

Rain makes you cold faster than you’d expect. According to the National Weather Service, water carries body heat away up to 25 times faster than air of the same temperature. That’s why a wet cotton hoodie at 50 degrees feels like a much colder day.

So a rain outfit really has one job, and that’s keeping the middle layer dry. The shell, coat or umbrella on top takes the water, and the hoodie or tee underneath can stay the same one you’d pick on a dry fall day.

You don’t need hiking pants and a poncho for that. In the rainy day outfits for men below, the rain gear is one or two pieces, and the rest is the same streetwear you’d wear in October. Eight of them wear a nylon shell, four a long coat, and four carry an umbrella.

Your base can come straight from my fall outfits for men. I’d start with the shell, because it decides how much the rest has to do.

Rainy Day Outfits for Men Start With the Shell

A shell is the base of most rainy day outfits for men: a thin, unlined nylon jacket with a hood. It keeps water out and adds almost no warmth, so it goes over a hoodie in October and a fleece in December.

Two details decide whether it works. It should reach past your waistband, or the rain runs off the hem and straight into your jeans. And the hood needs a drawcord. If you’ve ever had a hood blow back on the first corner, you know why.

1) An Olive Shell for a Rainy Day Commute

Halfway across the crosswalk with a steel water bottle, this is what a good olive shell does for you: you stop thinking about the weather. Navy nylon pants gather above the ankle, so the hem never touches the street. Olive goes with almost every other color. I’d buy this one first.

2) A Blue Arc’teryx Shell With Sage Cargos

Wet leaves on stone steps, a blue technical shell zipped to the chin and a crossbody strapped over it. The blue works because everything below it stays muted: sage cargos and grey trail sneakers.

Those cargos are cotton, though, and they pool on the shoe. In the first puddle they’ll darken from the hem up, which is the problem two sections down.

3) A Brown North Face Shell With the Hood Cinched

Both drawcords pulled until only the eyes show. A brown and grey North Face shell over grey cargo pants looks warmer than black, and the cinched hood is the detail that matters. You could ride a bike through a downpour like this and keep your hair dry.

Waterproof or Water-Resistant? How to Tell

Most shells say one of the two words, and the difference decides how long you stay dry. A water-resistant jacket has a coating that makes rain bead up and roll off. That holds for a short walk. In steady rain the water soaks in at the seams and the shoulders.

A waterproof jacket keeps going. Three things on the label or the jacket itself tell you which one you’re holding:

• Taped seams. Turn the jacket inside out. A waterproof shell has thin tape over every seam, because each stitch is a tiny hole.
• A water column in millimeters. It’s the height of water the fabric holds before anything gets through. When two jackets list it, the higher number keeps out heavier and longer rain.
• A flap or a sealed zip. An open zipper lets water in down the whole front.

If you’ve ever had a jacket that seemed to stop working after a year, you know this moment.

When the rain stops beading and the fabric looks dark and soaked, it usually isn’t leaking. The coating has worn off. A wash and a reproofing spray bring it back, and you’ll find both kinds of shell in our men’s jackets.

Rainy Day Pants That Don’t Drink the Puddle

Wide pants are the shape of the moment, and they bring a problem nobody mentions.

A hem that stacks on the shoe drags through every puddle, and cotton denim pulls that water upward like a wick. By lunch your jeans are wet to the shin while your jacket is dry. You’ve probably had that day.

The first fix is pants that don’t hold water. Nylon track and parachute pants take up very little of it, so a splash dries off on the walk.

4) A Black Track Suit With the Hood Up

Hands pulling the hood down over the face, back against a shutter, a Supreme waistband peeking out. A black nylon track suit with teal trail sneakers covers you from head to ankle in one material. It’s the simplest way to dress for rain without owning any rain gear at all.

5) Black Parachute Pants Under an Arc’teryx Shell

Sitting on wet rocks in a sage shell, hood up over a beanie, you’re dressed for weather that would ruin jeans. The black parachute pants have toggles at the ankle that lift the hem above the shoe. Worn back in the city, the same fit still reads as streetwear because the pants stay wide.

How to Wear Jeans on a Rainy Day

If jeans are non-negotiable for you, the cuff does the same job. One or two rolls bring the hem above the shoe, and the water has nothing left to climb.

6) Dark Jeans Cuffed Above the Shoe

A coffee, sunglasses parked on a camo cap, and a washed grey work jacket over a hoodie. The wide dark raw jeans carry a deep cuff that shows the light inside of the denim, and it stops a good inch above the street.

7) Olive Trousers With a Deep Cuff

A mustard chore jacket over a striped shirt, wide olive trousers rolled almost to the ankle bone, and brown leather boots on a lug sole that won’t mind a puddle.

My rule for rain is that one waterproof piece is enough. This fit has none at all and still gets through a drizzle, which tells you how loose that rule really is.

Both fixes have a catch. Nylon swishes when you walk, and some people hate that. Deep rolls catch splashes. For a short walk, both still beat a soaked hem.

Shoes for Wet Streets

In rainy day outfits for men, suede is the worst thing you can put on your feet. It soaks through and stains at the toe, and then it dries stiff.

Smooth leather, rubber and trail mesh on a thick sole all do better.

Mesh is the catch, because a trail sneaker without a membrane gets wet as fast as any runner. For a real downpour I’d look for a GORE-TEX version. We sorted the fall shoes for men that handle rain in more detail, and the men’s shoes go further.

8) Trail Sneakers Across a Creek

This is the shoe test nobody plans. A navy Stüssy coach jacket, grey hood up, olive cargos and cream trail sneakers hopping from stone to stone over a creek. A sole that grips wet rock will grip a wet subway stair too.

9) Platform Dr. Martens on Wet Asphalt

Gloves and a cap dangle from the belt on shiny wet asphalt. Black platform Dr. Martens carry a padded bomber, a turtleneck and olive cargos. Smooth leather on a high rubber sole is about as rainproof as a shoe gets, and the weight is the price. You’ll feel it by evening.

10) Black Leather Derbies With Olive Cargos

Black leather derbies sit under olive cargos, with a black leather jacket over a hoodie and an olive cap. Derbies look sharper than boots and still keep water out. Wipe them dry when you get home and the leather lasts for years. They’re my pick for work.

Wear a Cap Under the Hood

A cap under the hood is a simple trick with a real reason behind it. The brim holds the hood off your forehead, so the rain lands in front of your face. And when you turn your head, the hood turns with it.

A cotton hood soaks in steady rain, though. For real rain the hood belongs to the shell, and the hoodie stays dry under it. My hoodie outfits for men go deeper on the hoodie itself.

11) A Green Brim Under a Grey Hood

Only the green brim pokes out of the grey hood, and that little bit of color is what makes the fit. The hoodie sits under a sage work jacket with olive work pants and white leather sneakers. The jacket covers most of the cotton, and in light rain that’s enough.

12) A North Face Hood Over a Navy Cap

This is the version for real rain, standing on the rocks by the sea. A navy North Face jacket brings its own hood over a navy cap, with light wide jeans and a key clipped to the belt loop. The waterproof hood takes the rain, and the cap keeps it where it should be.

Rainy Day Outfits for Men With an Umbrella

An umbrella changes the whole outfit. It covers your head and shoulders, so wool, knits and a coat can stay on top without any rain gear.

What it doesn’t cover is everything below the knee. Wind and splashes still hit your hem and shoes, so the umbrella moves the rainproof part of the outfit down. I’d pick the umbrella for anything with a dress code, and you’ll see why further down.

13) A Clear Umbrella in Tokyo Rain

A taxi rolls past, the street is soaked, and the clear umbrella lets you see every bit of it. Under the dome, the grey hoodie and light wide jeans stay dry. The canvas sneakers are the weak point. Canvas soaks through in the first puddle. Swap them for leather.

14) A Logo Umbrella in Black and White

A big white Stüssy logo across a black umbrella, a black hoodie and navy track pants with side stripes, at a New York crossing with a yellow cab. When the umbrella carries the graphic, the outfit doesn’t need one.

15) A Black Umbrella and a Long Wool Coat

A black compact umbrella and a black beanie go with a long wool coat over a grey knit. The dark raw jeans are cuffed above black leather shoes. Wool keeps its warmth through a light drizzle, and the umbrella makes sure it never gets more than that.

An umbrella has two real weaknesses. It’s useless in strong wind. It also keeps one hand busy all day. On a windy day the shell wins, and on a calm day in nicer clothes the umbrella does.

Rainy Day Outfits for Men at Work or on a Date

When the day needs you to look sharp, the umbrella and a long coat are the way to do it. A trench was made for rain in the first place. Its tightly woven cotton sheds light rain, and the length covers your trousers to the knee.

16) A Navy Coat, a Blue Sweater and a Croissant

Umbrella in one hand, a croissant between the teeth, wet cobblestones under burgundy loafers. A navy long coat goes over a royal blue sweater and a white collar, with cream wide trousers.

Cream is risky in the rain, and the umbrella is what makes it possible. It’s the most dressed-up fit here, and it still looks like fun.

17) A Grey Trench Over Wide Black Trousers

A grey trench hangs open over a grey henley, with wide black trousers and black shoes. Grey and black barely show water, so nobody will see the rain on you. You could walk into an office or a dinner in this without changing a thing.

18) A Beige Mac With the Cuffs Rolled

A beige mac with the striped shirt cuffs folded over its sleeves, a navy polo and dark jeans. The rolled cuffs keep the coat from looking like it belongs to your dad.

A cotton trench has a limit. In a long downpour it soaks through at the shoulders, so on those days it needs the umbrella. A dark one hides it better than this beige one.

Cold Rain Calls for Fleece

Near freezing, the cotton layer under your jacket becomes the problem. If it gets damp, it stays damp and cold. If you’ve ever sat through a lecture in a wet hoodie, you know the feeling.

Polyester fleece works differently. It takes up very little water and keeps some warmth even when it’s wet. In steady rain it goes under the shell, and in light drizzle it can be the outer layer.

19) A Brown Fleece Jacket With Light Jeans

Snow on the trees behind, a brown fleece jacket with light piping, a light blue cap and light wide jeans. Brown fleece looks less sporty than black and goes with denim the way a suede jacket would.

In rain, the same fleece goes under the shell from the top of this post. When it’s properly winter, everything here carries on into my winter streetwear for men.

Warm Rain: Shorts Under a Light Shell

Summer is the easiest season for rainy day outfits for men. It’s warm, so the shell can be thin, your legs can stay bare, and the only thing you really need to keep dry is whatever you’re carrying in your bag.

Skin dries in minutes, while wet jeans stay wet until evening. That’s why shorts are the smarter choice when it’s warm and pouring.

20) Jorts Under a Navy Anorak

Headphones on, eyes on the phone, a navy anorak over a grey tee with dark denim jorts, white socks and silver running sneakers. The anorak’s hood sits ready behind the cap. Jorts are denim, so they soak, and they’re still dry by dinner.

21) Cargo Shorts Under a Beige Shell

Zipped up to the nose with both arms hugged tight in a wet parking lot, this is the honest picture of warm rain that turned cool.

A beige hooded shell goes over black cargo shorts, white socks and black sneakers. The shell did its job, and the shorts are why you’d be cold. Keep this one for summer.

Before You Leave the House on a Rainy Day

All of these rainy day outfits for men follow the same idea. One piece takes the water, and the rest stays dry enough that you still look like yourself at the door.

On a rainy morning, I’d check four things before you go out:

• Your outer layer is a shell, a long coat or an umbrella, and it covers your waistband.
• Your hem ends above the shoe, or your pants are nylon.
• Your shoes are leather, rubber or a trail sneaker, and none of them are suede.
• If the hood goes up, there’s a cap under it.

Start with a waterproof shell with taped seams, because it covers every other outfit you own. The shoes come second.

And when the rain turns into sleet one morning, the shell stays and only what’s under it changes.

Questions About Rainy Day Outfits for Men