in: Accessories, Style

• Last updated: September 25, 2021

The Gentleman’s Guide to Umbrellas

Vintage gentleman with umbrella standing on the road.

Editors note: This post was a collaboration between AoM and AoM reader David Bastistella who went on the search for a proper umbrella and supplied us with some great info from the hunt.

“It’s a big enough Umbrella, but it’s always me that ends up getting wet.” -Sting

Unfortunately, this was the case for me a few weeks back when I grabbed my trusty collapsible red umbrella for a trek out into the rain.  Of course I was sporting my best raincoat to go with it, but on this day, the rain, and particularly the accompanying wind, would push me over the edge and find me jamming my cheap umbrella into the nearest public waste bin. The remaining walk to my destination with a cold hard rain on my forehead left me with nasty sinus congestion.

I didn’t need the cover at first.  The forecast was only calling for light rain.  The torrential downpour that claimed yet another ninety-nine cent umbrella pushed me to this writing and the journey toward finding a proper gentleman’s umbrella.

Some of the world finest umbrellas, I would learn, are from Great Britain from a company who ensures the royal family keeps their hair intact in even the worst London downpour.  Others from Italy carry the style, design and craftsmanship we have come to know from the artisans of that country. Still others demonstrate that umbrella design has not remained unchanged, and on the horizon are new shapes and new technologies that will keep us, and possibly more importantly, our clothes, clean and dry.

My guide to sorting through this world of umbrellas was Bobi Jurcic.  She runs a store in the lower level of the Fairmont Royal York Hotel called, appropriately, Raindrops. She helped me sort through the numerous umbrella choices.

The History of the Gentleman’s Umbrella

The first incarnation of the umbrella was the parasol, which was designed to shade the user from the sun, rather than to keep rain off the head. The parasol dates back to numerous ancient civilizations, in which it was employed by slaves and servants to shade the heads of kings and other members of the ruling class. Despite this tie to masculine royal power, over the centuries the parasol and the umbrella would come to be associated almost entirely with women, who used these handheld canopies to temper the heat, keep the sun off their delicate skin, and prevent the rain from ruining their clothes.

One man grew tired of gentlemen being expected to trudge through the rain or hail a coach to get out of the downpour. Around 1750, Jonas Hanway began stepping out with an umbrella. While he initially met with ridicule, other gentleman quickly saw the wisdom in carrying such an accessory and adopted it as one of their signature pieces.

Jonas Hanway first englishman umbrella illustration.

Gentlemen of the past often carried an umbrella merely as an accessory, never once unfurling it. But such impracticality does not suit the modern man. Today the umbrella, along with such things as the handkerchief and pocketknife, is an important part of a gentleman’s arsenal. An umbrella can keep you and your duds dry, but even more importantly, it’s there to extend to a lady who is getting summarily drenched. So invest in a well-made brolly. A quality umbrella earns you style points and can last you over ten years.  Keep that in mind when your dollar ninety nine special leaves you blown back and wet.

Umbrella Buying Tips

When looking for a proper gentleman’s umbrella, check several factors before making your purchase.


The canopy is obviously a central part of an umbrella. If it’s not watertight and well-made, then the umbrella serves no purpose. Check to be sure the canopy does not sit loosely on the umbrella’s ribs. Open the umbrella and flick the segments with your fingers to test for tautness. Then hold the open umbrella up to the light to look for any obvious defects.


A quality frame is made to stand up to the wind without collapsing. Aluminum frames are cheap and light, but will often crumple when faced with a strong wind. Look for nickel, brass, fiberglass, or tempered spring steel.


Rivets are used where the ribs connect and bend. Hollow rivets that you can see through are subpar. A solid rivet ensures that your umbrella will last through many years of being opened and closed.


The shaft is really only an issue on full-sized umbrellas (not the compact, telescoping variety).

It’s important to get the right length of umbrella for your height so it is comfortable to carry and use. High end umbrella stores will have you experiment with a walking stick to find the best length for you. They then saw off a chunk of the shaft of the umbrella you have selected to get it to just the right height.

Also, keep in mind that the shaft comes in various builds:

Solid stick (1 piece): A solid stick umbrella is made just like the name suggests-of one continuous piece of wood. Compared to a metal shaft, the solid stick shaft is heavier and thicker and you won’t be able to furl up the canopy as tightly. But solid sticks are quite sturdy and allow the gentleman to use his umbrella as an occasional walking stick.

Fit-up (2 piece): Fit-ups are made of two pieces of wood and are lighter than the solid stick.

Tube: The shaft of a tube umbrella is typically made of steel and as the name suggests, is hollow. A tube shaft is lighter and allows the umbrella to be wrapped up tighter than the wooden varieties. But it is also more prone to bending than a solid stick.

Types of Umbrellas

There are two basic styles of umbrellas.  Each has their pros and cons. In either style, Bobi recommends basic black for men, but there are colors, fabrics and style choices to suit any taste.  One must of course feel the umbrella and consider it not only for its purpose, but how it will impact your style and possibly even heighten your rainy day.

The Traditional Full-sized Umbrella

The full-sized umbrella can double as a walking stick, get you out of a pinch in a dance number, and act as a weapon against ruffians who accost you in the street. It’s hard to beat a well-crafted manual umbrella with a good solid wooden hook handle, which Bobi tells me is very handy for hanging over your arm or in a closet when not in use.  With its wider horizontal reach and deeper dome, the full-sized umbrella obviously offers great coverage. But perhaps its greatest advantage is how it performs in the wind.  The longer stems that form the spine of the machine prevent it from folding back in high wind.

Checkpoints for a Full Sized umbrella

  • Black with a good wooden handle is the best bet
  • Look for good construction and mechanisms
  • Go for subtle patterns for style
  • Always leave open to dry
  • Price Range from $40-$500

The Automatic Collapsible Umbrella

Collapsible umbrellas may not have the panache of their full-sized brothers, but they’re compact, convenient, and tuck neatly into your briefcase or car for unexpected rain. Before cheapo imports diluted the market, collapsible umbrellas were a status symbol and a regular gift for holidays from Christmas to Communion. Their smaller size goes anywhere, and in the case of well crafted models, open effortlessly with the touch of a button. They’re quite handy, with more mechanics and a spine system that is comprised of multiple pieces.  These umbrellas also can be found in a variety of colors and styles, and you can even find one with the smart wooden handle we all love.

Checkpoints for an Automatic Collapsible Umbrella

  • Look for a good dome
  • Easy open, easy close
  • Firm solid hardware construction
  • Always leave open to dry

High Tech Umbrellas

If technology is your thing, you might want to consider a couple of new, cool designs that have been developed recently.

Senz Umbrella

Senz umbrella modern gentleman's accessory.

The Senz’s aerodynamic design keeps rain off your back and can withstand 70 mph winds.


The Windbrella’s design allows the wind, but not the rain, to pass through the umbrella.

Wi-Fi Camera Umbrella

Wifi camera umbrella taking picture at night.

Another futuristic option is the new Wi-fi umbrella which has high-tech gizmos integrated into the traditional umbrella design. This umbrella allows you to take pictures with the umbrella, instantly download them to Flickr, and then with a flick of the wrist, see your pictures projected on your umbrella “screen.” It also comes with GPS and a digital compass.

Special Umbrellas

While a traditional, well-made umbrella is the most appropriate choice for a gentleman’s brolly, sometimes it’s also nice to have something with a little flair and sense of fun. Especially something that makes you feel like a spy.

Unbreakable Umbrella for Self-Defense

It’s a fully functional umbrella that’s unbreakable from canopy to handle and can be used for hanging from bridges and going all bartitsu on some scalawag. You can use it for the kind of fancy moves seen in this video, or just for general whacking purposes.

Be sure to watch the whole video; you don’t want to miss the man using the umbrella to go to town on a heavy bag.

Blade Runner LED Umbrella

Blade runner umbrella with a LED-lit shaft.

Using an umbrella on a dark and stormy night, you may need some light to illuminate your path. They make umbrellas with flashlights in the handle, but these umbrellas with a LED-lit shaft are far cooler. Modeled after the umbrellas in the movie Blade Runner, they also look quite a bit like light sabers.

Umbrella with Built-in Pencil

Umbrella with pencil in handle close up.

While designed for the man who takes to the race track rain or shine, these umbrellas hardly offer a modicum of practicality (it’s pretty easy to carry a pencil in your pocket). But there’s something neat about having a pencil built into the handle of your umbrella. (Anything+secret compartment=awesome).

Samurai Sword Umbrella

Samurai sword umbrella.

If the light saber umbrella doesn’t quite hit your geek sweet spot, perhaps this Samurai umbrella will do the trick. It comes with a sling for your back, so you can draw your umbrella at any time and banish the precipitation with it. And if you commit a shameful act, and must therefore fall upon it, you won’t die.

Sword Umbrella

Sword umbrella modern man gentleman accessory.

This umbrella doesn’t look like a sword— it is a sword. One button releases the umbrella, the other a real sword. Spy-tastic.

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