The other day, I wore my favourite pair of basic black ballet flats to work and as I walked down the street, it suddenly dawned on me: it was no longer ballet flat wearing season. Man, my feet were cold! 

With the tempermental weather this time of year (when it's not brisk and chilly, it's downpouring with rain), finding a good pair of shoes to combat the elements is difficult. You also want to find a pair that are comfy and can withstand a good shopping spree. To find a good pair of shoes that does all of this and that also happen to be cute, is even more difficult. But certainly not impossible! 

I found five pairs of shoes for you to try out this season that will keep you toasty and dry, are all day comfy and chic to boot! Plus, included are some pieces of street stylspiration from around the globe, for easy and stylish tips on how to wear them in cute, trendy and fun ways. 

#1 Sneakers: Take note, tennis shoes are back and super cute to wear with anything from denim to leather to feminine skirts. 


(images via lookbook.nu, thestreetstyled.com) 
 
Try: Converse Baruth Sneakers in Red (C$60.00)

#2 Riding Boot: You can still do all your downtown shopping in these even when the snow is falling. They give an outfit an upscale and classic look. 


(images via lookbook.nu, lefashionimage.blogspot.ca) 

Try: Bandolino Cavanna Classic Riding Boot (C$149.99)

#3 Wellies: Think rain boots are only for kids? Think again. Try a bright colour for a quirky vibe and experiment, pairing them with sweet, playful dresses. 
 

(images via whatiwore.tumblr.com, atlantic-pacific.blogspot.ca) 

Try: Hunter Welly Tall in Navy (C$149.99)

#4 Ankle Boots: Heeled ankle boots are fabulous for fall, but their wearbility factor for those of us on the go, is a bit questionable. Try a flat ankle boot paired with skinny jeans. This look is effortless yet looks great when pulled together with a funky sweater or jacket.  


(images via theboominyourroom.blogspot.ca) 

Try: Dune Paddington Studded Ankle Boots (C$157.54)
 
#5 Oxfords: For a more formal occasion, try an oxford flat. They're dressier than a sneaker or boot and uber trendy for fall. If you're adventurous, try a metallic, print or even a simple patent black if you want to be able to wear them with any outfit. 


(images via fashionologie.com, atlantic-pacific.blogspot.ca) 

Try: Nine West Boutique 9 Milton (C$180.00)

Are any of these styles calling out to you?