Fall Winter Wardrobe Staples

Okay, for those of you who follow both the blog and my IG, you may have voted on what you wanted to see for this week’s Thursday’s Three. I was a little shocked to see most people asking me for fashion! But I’m so here for it. I also guess you guys enjoy it when I stick to a theme for the week!

I struggled for a while re what type of fashion post to give you. I eventually decided since I’m a pretty basic (okay, maybe we can call it classic LOL) person when it comes to fashion, I should stick to my classics and share my top fall / winter wardrobe staples. 

After my mega closet clean-out on Tuesday, I was definitely re-inspired by my wardrobe and have worn “real people clothes” (i.e., not lulu’s) since doing it. It’s like a whole new world getting back into something you haven’t cared about for a few years, but an exciting world. So I’m actually very thankful that you encouraged this post!

Without further ado, here are my top three transitional winter wardrobe staples that anyone can rock, any time.


Signed Samantha's winter wardrobe staples includes a plaid shirt - as she is wearing in this image with a plant in the background.

Flannel/Plaid Tops for Fall and Winter

Flannel and plaid tops, I feel like, are a perfect transitional piece that you can start wearing in the fall and keep it as a winter wardrobe staple.

Growing up in North Vancouver, arguably one of the world’s plaid capitals, plaid is something that’s been a winter wardrobe staple for pretty well my whole life – and let’s be honest and not limit it to just fall and winter. There was a time where it was one thousand percent an all-year-round staple.

Flannel and plaid are super versatile and are items things you can wear with pretty well anything: jeans, leather, skirts; you name it, you can probably make it work together. The other thing I love about it is the pattern choices you get; you can go as bold or as subdued as you want – the choice is totally yours.

Finally, have you heard of shackets? Yeah, it’s a jacket that looks like a shirt and is very on-trend right now. I’ve linked some of my favourite fun plaid shirt and shacket options below. The exact plaid shirt I am wearing is Grayson and I got it at Anthro – for some reason I cannot find it to share it!


Signed Samantha's winter wardrobe staples includes a plaid shirt and faux leather leggings which she is wearing sitting on the ground.

Faux Leather Pants For Fall and Winter

During any other normal year, I would be living in my leather leggings as soon as fall hit. They are definitely a fall transitioning to winter wardrobe staple of mine.

I’m so obsessed with faux leather leggings, pants, joggers, and honestly faux leather bottoms of any sort. These aren’t technically faux leather leggings either; they are a coated jean but look like they could be leather, so I’m totally going to categorize them as leather.

I have always found that you can dress it up or dress it down and that a faux leather bottom is typically exactly the perfect piece for (almost) any occasion.

I usually go for black, but there are so many fabulous options out there for colors. Not to mention, they also pair well with pretty well everything, plaid (duh!), oversized sweater, casual crew neck sweater, t-shirt… Honestly, the options are endless. I suppose that’s why I’m calling it a winter wardrobe staple. 

P.S – I desperately need to print that art for the wall above my sofa LOL.



Signed Samantha's winter wardrobe staples include faux leather leggings, a good pair of boots, and a plaid shirt. All items she is wearing in this overhead shot of her legs, feet and a portion of her torso

A Solid Pair of Boots for Fall and Winter

There is nothing better than an awesome pair of boots – which is why I saved it as the final item in this winter wardrobe staples feature. You will see my enthusiasm for boots as I actually linked a million (okay, a little less than that) options for you. 

These heel booties are Sam Edelman from last year, and I can’t seem to find the same ones this year, but not to worry, there are a ton of other options that I’ve shared – from expensive, to affordable.

Anyways, boots, again, have so much versatility in what you can wear them with. These heel booties glam up this existing outfit; I could have worn them with a skirt, a pair of jeans, a pair of dress pants.

Again, the key to becoming a staple in my closet is versatility. Many, many boots have a lot of versatility to be able to wear throughout the fall and winter. Plus they are darn cute!


What do you think of my transition from fall to winter wardrobe staples? Are they on par with yours, and if not, I’d love to hear what I should add to the list!



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  • Janet

    Great list and awesome array of options that you included! Super helpful. Thanks for doing the hunt for all of us /and cheers to warm and cozy winter outfits!

    • Samantha

      Thanks so much, Janet. I definitely had a lot of amazing help and guidance getting back to “me”! I figured I should share the goodies. Double cheers to warm and cozy outfits!! XO

  • Erin

    Love all of these pieces & how they pair perfectly together! I need to invest in a pair of faux leather pants – so stinkin’ cute! Definitely inspired to do some fall shopping now. 😉

    • Samantha

      I’m glad I could help inspire you! I am a minimalist when it comes to my wardrobe and if it doesn’t all match, I will struggle LOL!!! Happy shopping. XO

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