Regan: Pilots in Pillow Boots


Hobby pilot Regan flies across the Manitoban prairies in all weather. She wears our Pillow Boots to keep warm in the cockpit.

1 min read

One of the youngest students to complete flight school, Regan’s been flying since she was 16. Not afraid to blaze a trail, she needs comfortable, stylish clothes to stay safe and warm in the air.

When did you know you wanted to be a pilot?

I told a family friend that I really wanted to try flying and he offered to take me up in a single engine plane that fall. During that flight I completely fell in love with flying. Right after that I started looking into flight schools and the rest is history - I am now 18 and a hobbyist pilot!

What's the hardest thing about dressing for flying?

When you fly in single-engine four seat Cessna planes like I do there’s typically one thing that stands out the most: there isn’t a lot of room in them! So when it comes to dressing for flying, whether you are a passenger or the pilot, you want to be as least bulky as possible. As the pilot it is even more important to be able to move freely at all times. You have to be able to reach every part of the control panel with ease. Free movement of every part of your body is very important.

How do you decide what to wear in the morning?

I am absolutely a comfort first girl… always have been. I also am a fan of simplicity.

Fall is by far my favourite season of the year. The boots, sweaters, cozy jackets, cute toques and hats, warm pumpkin spice chai lattes, fuzzy scarves and colourful atmosphere never ceases to cheer up my disposition. You will see me utilizing sweater and cute boot season to the uttermost because of my love for it! I really love that being stylish and warm are going hand in hand with a lot of Cougar boots.

What made you choose Pillow Boots as your flight boots?

I had a very hard time finding shoes that kept my feet warm while flying in the middle of our Manitoban winters. I had never heard of Cougar before seeing them in a store, but I decided to give them a shot.

I was hooked on their warmth and comfort after my first flight with them. Plus they are fashionable! Which, being a female, is kind of important to me. Even more so now because I was the first, and only, female to go through my flight school, plus the youngest student to go through flight school at the age of 16… I like to try and stay comfortable and cute while doing what I love.

You have a time machine. What time and place do you travel to just for the clothes?

Definitely 1940s. The United Kingdom, Canada, and the United States all had a similar style and if I had those style dresses in my closet, I probably would be walking around in them all the time!

Check out Regan's review of our new Blackout Leather Boot, a special all-black version of our classic Pillow Boot.

Regan is wearing the Blackout Leather Winter Boot.

Photos courtesy of Regan Wiebe

Regan's picks

Gladstone Leather Ankle Boot

Anton Suede Ankle Boot

Dart Duck Bootie

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