As someone who has their fair share of gear and technical clothing for all manner of conditions and environments, I've spent a good amount of time in shops and researching online over the years.  I like to buy the right thing the first time, saving money where I can, and I have some tips below so that you can do the same.

Some of my savings from the past few years: 

• 35-50% on Arc'teryx pants and belt

• 40-60% off Solomon and North Face hiking shoes and boots

• 40-60% off Keen sandals

• 40-70% off Icebreaker tops and jackets

• 35-40% on Osprey luggage

• ~$200 on a Gore-Tex shell
  

As you can imagine, I never pay full price for clothes and gear (unless I can’t help it).

Some of the examples and stores will be Canada-centric, but you can find local equivalents for where you are. If you have some to add, feel free to share them in the comments below. A link to some resources will be at the bottom of the page.

Know Your Size if You're Buying Online.

If you're buying online, it's critical to know what your size is.  It is important to remember that a "medium" from one brand may have a different fit compared to the same size from another brand.

In my case, a size small top from Icebreaker is always a great fit for me, and a size 28 Arc'teryx pant will also be a perfect fit.  This is one of the reasons that for the last decade or so, I've bought these two almost exclusively (their unmatched quality and feel are the others). 

Research In Advance, and Wait

Well in advance of needing it, I'll think about that new piece of gear, be it new boots, new luggage, or a new Gore-Tex jacket.  After watching prices for a short while, or comparing a retailer's price with the manufacturer's website, you can easily spot what the going price is versus the regular retail price.

This way you'll begin to understand what a *real* deal looks like for that product.

Buy at the End of the Season For Next Year

While it may first seem counter-intuitive, buying at the end of the season is a good time to save big for the following year.  For example, if you're looking for a great deal on a pair of winter boots and your current ones can still make it through this one last season of snow and ice, the end of winter is your best bet for a deal on a new pair for next year.

The big end of summer sales tend to happen early in the fall, and the big end of winter sales happen in the spring.

Sales Are Predictable

A good option for outdoor gear and footwear in Canada is Atmosphere.  Several times a year, they offer 25% off on almost everything they sell (with a few exceptions, like Arc'teryx).  So jump on the mailing lists of some of your favorite stores and eventually you'll be able to see a pattern emerge.

In the case of Atmosphere and Sport Chek (they have the same parent company), if the product I am looking to buy isn't on sale right now, I know that it almost certainly will be sometime in the next 8 weeks.

I bought a pair of Osprey rolling luggage bags at Atmosphere by waiting for the right deals to come around.  By combining a "Friends & Family" sale I had been waiting for with a new e-mail signup coupon (10%), I managed to stack them both together and saved nearly 35%.

See how I pack my Osprey rollers in How I Pack My Photography Gear and Life for 5 Months and 4 Seasons Abroad.

Clearance Can Be Your Friend (But Be Careful)

A clearance deal for last-year’s model or other discontinued stock can be a good place to find a deal.  That deal may come with a different return policy, so keep that in mind and confirm in advance.

For example, The Last Hunt offers clearance deals on a number of outdoor and adventure brands, but since every item is a final sale, it's not a good option for buying something that you're not 100% sure will be a great fit.

This makes a local option a much safer bet for picking up “final sale” deals so you can at least try them on before you hand over your hard-earned money.

I had been looking for a replacement Gore-Tex shell when I happened to be at Mountain Equipment Co-Op a few years back.  Flipping through the options on the carousel, I spotted a great one in my preferred black, but at $400, it was more than I wanted to spend.  Then I noticed that the bright orange version was being cleared out for $225.  Obviously "vibrant orange" wasn't the top choice for many people, and while it wasn't my top choice either, it was worth it to save $175.

Like they say with cars though, don't buy the car you want with the wrong color paint job.  For me, the orange was fine, but it's not worth it if you're going to hate it every time you put it on.

Look For Outlet Stores

This one can be a little hit-or-miss because you can’t trust all outlet stores.

That said, I will drop into a local Icebreaker Outlet store when I have a chance, and I have purchased a 3 jackets and a few shirts when I’ve visited them in New Zealand, Australia and the USA. While the selection is often a gamble, you can save some big bucks (particularly if my friend Sandy is with you to negotiate further at the till. Yes, that’s a thing! Thanks Sandy!)

Some Brands Almost Never Go on Sale, Others Seemingly All of the Time

Brands like Arc'teryx almost never go on sale in retail shops (besides clearance) due to an agreement with the retailers.  So unless you can find an end-of-season clearance deal, you're likely out of luck.  I get most of my Arc'Teryx pants at The Last Hunt, though I've lucked out with a clearance sale directly on Arcteryx.com as well.

Canadian outdoor retailer Mountain Equipment Co-Op famously never had any sales (besides clearance sales) until more recent years.

On the other hand, you may notice that many house brands are almost always on sale.  That might give you a bit of an idea of their quality.

Buy Local If You Need It ASAP

While I always have a keen eye on price for the product I want, if I need something quickly and no deals are to be had, I'll default to a local independent retailer if I can.  They typically have the best-trained staff and they are worth supporting (unless I'm paying a bunch more for the privilege).

If You Don't Need It, It's Not a Good Deal

Finally, don’t buy stuff you don’t need or that is out of your budget.

Resources:

Shopbot.ca - While not clothing or gear specific, this can help you find current deals at Canadian online retailers.

TheLastHunt.com - The clearance / final sale arm of Canadian outdoor retailer Altitude Sports. Easy search filters help you narrow down your selection between brand, style, and size. Tend to bring in new product at lower discounts, and increase the discounts over time. Best place to get discounts on Arc’teryx.

Rakuten.ca - Shop through this site to get a little affiliate kick-back right into your wallet from participating retailers ranging from 1-20%. Sign up here to get $5 free when you first use the service. (I’ll get $5 too)

Icebreaker Online Outlet (Canada) - Free shipping and up to 60% off, but keep an eye on what is final sale.

Arcteryx Online Outlet (Canada) - Free shipping and returns. Typically a small selection.