In many situations, technical outerwear — while highly functional and advanced — is bunk. Yes, should you find yourself on a hike in Appalachia or halfway up the North Ridge of K2 or even out for a jog in Tupelo, Mississippi, you will benefit greatly from breathable waterproof this and taped seams that. And if you’re wearing it on your way to a meeting or arriving to a date, you’re just going to look like a jackass.

But what other choices do you have? Old-school waterproof outerwear like Macs and waxed cotton on their own will leave you stylishly damp and clammy, and abstaining from rain-repelling clothing altogether will turn you in to a less-dreamy version Ryan Gosling in The Notebook (yeah, we made a Notebook reference, happy Valentine’s Day). So we arrive at our solution — the umbrella.

“But every loser has an umbrella”, you’ll say. “How could that lame-looking thing replace my 500-denier Cordura® Gore-tex®?” The fact of the matter is a quality umbrella (bypass the guys selling them for $5 and learn not to lose stuff) paired with some classic, temperature-appropriate outerwear is and always will be the best way to stay dry and fly. With that in mind we picked five excellent umbrellas that run the gamut from compact to full-sized. You’re welcome.


Davek Mini

Since 2005 Davek has been the standard for stylish and incredibly durable umbrellas, and their hyper-compact Mini continues the trend at a very tolerable price point. Just seven inches long when closed, the Mini can be left in a desk drawer or bag until it’s needed. Davek’s unconditional lifetime guarantee will make sure it lasts as long as you can keep track of where it is.

Blunt Classic Umbrella

A seriously advanced umbrella, Blunt’s design uses something called a “Radial Tensioning System” to increase durability and make it hugely resistant to wind. Good Karma bonus: its “no sharp edges” design won’t stab your fellow pedestrians in the eye as you saunter by.

London Undercover Collapsible Bamboo-Handle Umbrella

Famous Umbrella Scenes If There Were Only Raincoats




A favorite of the #menswear set, London Undercover makes solid umbrellas with a good eye for color combinations and styling. It’s small enough to be left in a bag and sturdy enough to last many a rainy spring. If you’re looking to stand out on a rainy day, the orange version should do the trick neatly.

Filson Two Tone Umbrella

A classic umbrella by a classic company. Filson’s take on the rain-cover is about as traditionally styled as it gets and the two-tone design is like an interesting lining on an otherwise muted sport coat.

Swaine Adeney Brigg Malacca Flask

Welcome to the pinnacle. As you might imagine, rainy Britain is like the major leagues of umbrella makers, and rising to the top is no easy feat. Swaine Adeney Brigg was the royally appointed umbrella maker for Queen Victoria and Edward VI and currently supplies the Prince of Wales. How does a company gain such patrons? By producing (frankly insane) items like the Malacca Flask, which, along with its beautiful construction and optional silk canopy, boasts a screw-in glass flask for cheekily sneaking a sip of single-malt. If you’re less into foul weather boozing, you can save a few pounds by getting the standard Malacca.