Alexandra Gabris, a stylist at the boutique Espy, says the "Canadian tuxedo" is not a good look.
Instead, she suggests delving into one of this season's hottest trends: colour blocking. Try pairing a brightly coloured pair of jeans — in a turquoise or coral hue, for instance — with a similarly vibrant blouse. Then throw a more subdued blue denim jacket on top.
"This is a great way to do denim-on-denim without being too matchy-matchy. That's something you don't want to do for the Stampede," said Gabris.
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Fellow Espy stylist Amelia McIlmoyle suggests pairing a lace camisole with a form-fitting leather vest for a sexier, more updated cowgirl look.
"That's just going to give your body a little more shape. You're not going to be so dumpy. It's going to be cuter."
For the few Calgarians heading into the office this week, it's a fine balance between getting into the Stampede spirit and going overboard.
"The 'Daisy Duke' look, it doesn't fly in most offices. I would avoid that," says Brian Guichon of western wear store Riley & McCormick.
Instead of ultra-short cutoffs or miniskirts, a dark blue or black pair of jeans is more appropriate.
Or, McIlmoyle says, a flowy, feminine dress that skims the knee paired with a western-themed scarf, belt or jewelry.
Jen Huxtable, a stylist at Holt Renfrew in Calgary, suggests incorporating one or two Stampede-esque items into a work outfit.
"I think the biggest thing is not dressing for a theme Stampede party and rather picking one traditional Stampede style and working that into your everyday wardrobe," she said.
That could be a plaid blazer with a simple black pencil skirt, or a classic plaid jacket with dark denims.
There are also ways to add a twist to perennial Stampede pieces, said Huxtable. Instead of blue jeans, why not paisley print pants?
"Rather than your classic cowboy hat, try doing a straw fedora instead," she said.
Many Stampeders, however, are still going for the basics.
Riley & McCormick's Guichon said his downtown Calgary store has been twice as busy this year compared to other years due to the Stampede's 100th anniversary.
"Boots and hats and shirts and jeans and belts and buckles — everything is going."
There are cheap hats aplenty around Cowtown during Stampede, and a lot of people just pick one with no intention of wearing it once the festival is over.
"After a couple of days of heavy partying it kind of looks like they didn't pay a lot of money for it. They get beat up pretty easy," he said.
A decent wool cowboy hat will cost between $70 and $125. The best quality hats are made from rabbit or beaver fur, and will run you upwards of $180. They may be pricier, but they'll last longer and keep their shape better.
A hat has got to fit just right, said Guichon.
"The wind's not going to take it off, but it's not going to give you a headache," he said.
If you're Stampeding all day long, happy feet are a must. A cowboy boot with a rubber sole is durable and comfortable, but the downside is that they can get hot.
"Personally, I like an all-leather boot because leather breathes and leather is more dynamic. It's a natural fibre," said Guichon.
Jeans, Guichon said, are "a given."
"Denim is pretty consistent with sort of the cowboy uniform...You've gotta have some jeans on," he said.
"To men, I'd say don't be afraid to try on a pair of slim fit jeans."