Fashion / Style File

The Perfect Rainy Day Wardrobe for Men

How to Stay Chic and Dry

BY // 11.07.18

Hopefully, you are a fan of these prophetic words from Henry Wadsworth Longfellow: “Into each life some rain must fall.”

I moved back to Dallas in late 2015 after a two-year stint in Seattle. If you haven’t been to the Emerald City, then what you have likely heard is true — it rains nonstop. Might I suggest that if you have an inclination to visit, book your trip sometime between July 5 (in the Pacific Northwest they call the day after Independence Day the first day of summer) and anytime before Labor Day.

You literally have a six-week window to witness the Technicolor-green beauty at its best and brightest. And, of course, book a room that faces Elliott Bay at the Four Seasons. If you go any other time of the year, be prepared for some drizzly days.

I credit that sabbatical in Seattle to truly upping my fashionable-rain-attire game. I invested in some pieces that have come to be incredibly handy of late in Dallas — and much of the rest of Texas for that matter. This fall has been record-breaking in terms of a preponderance of precipitation.

So, you might ask what are some tips for creating chic, flood-zone-ready attire?

To quote Rihanna, “Now that it’s raining more than ever… You can stand under my umbrella.” That magical device is the ultimate in utilitarian — but it has always been, to me, the coolest of accessories.


Growing up, I remember seeing my first vintage episode of The Avengers and thought, “How dapper is John Steed? And his umbrella turns in to a sword?”

Then, later I became a huge James Bond junkie. Q often seemed to provide 007 with a new variation on the umbrella-cum-weapon. BTW — International spy was my fantasy career, but instead I ended up a denizen of museums.

Rain Day Gear

As I pen this ode to the umbrella I realize that it would quickly turn in to a novella, so instead, I’ll cut right to the commerce chase. Here are a few a few stalwart umbrella options to consider:

Burberry, the quintessential British luxury-goods company provides a few choices, since Londoners generally have 350 of the 365 days of the year to take advantage of the accessory. Might I suggest one with the iconic plaid cloth and a simple leather handle for everyday wear.

Then for those dressier occasions, you can’t go wrong with a simple all-noir, brass-hardware Alexander McQueen. With one of the fashion house’s signature skulls at the end of the handle, it’s the ultimate exclamation point to mark your entry into a room.

I’ve recently discovered London Undercover. All of its options come at incredibly accessible price points. To channel your inner urban commando, purchase the camouflage option tout suite.

Next, you’ll need some great footwear for trotting through city streets filled with puddles that pop-up like land mines.

J’adore my Gucci rubber rain loafers. I’ve gotten so much use out of my black pair (which is often mistaken for patent leather). Over the past few years, I’ve seen the swellegant label offer them up in myriad colors. I am now coveting a red pair (akin to Dorothy’s ruby-red slippers).

Hunter Wellies. Need I say more? The venerable company has been making them since 1856. Renowned for its iconic Original boot and holding two Royal Warrants of Appointment to HM The Queen and HRH The Duke of Edinburgh, I believe in Hunter’s claim to “Forge designs that shield pioneers from the elements and the bleakest of landscapes.” I’ve always secretly fantasized of becoming a Sloan Ranger — and I guess all I now need is a Range Rover and a Sloan Square address, as I already have too many Hunter Wellies to count.

I’ve included a pic of my recent rainy-day ensemble in the photo gallery above this story. I went with a nifty green Lacoste with a new twist: Instead of the traditional polo collar worn by countless tennis stars, this shirt has a built-in hood. Underneath, I wore a white button-up (with button-down collar) Brooks Brothers shirt, as all true preppies favor layering. An Hermès belt (silver buckle with mauve leather) was holding up my slightly oversized cut-off Vineyard Vines khakis. (Once again, a true prep never throws things away, so who cares if you’ve lost some weight? Just tighten your belt and cut-off that pair of once-long khakis.) And, of course, I finished it all off with Hunter navy blue Wellies.

Hopefully, this is a bit of a primer that you will have ready for the next time that Annie Lennox proclaims, “Here comes the rain again.”

For you ladies out there wanting some advice on water repellent items to add to your wardrobe, click here.

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