Thoughts on My Winter Wardrobe + Last Few Winter Outfits

Her Simple Sole - Thoughts on My Winter Wardrobe - Last Winter Outfit #2

The first full season I truly focused on being intentional was with my 2020-21 winter wardrobe – I touch on some of my wardrobe purchases in my 2020 low buy year recap. Along with fall, it’s my favourite style season. I just absolutely love layers and the cozy feel of knitwear.

Now that it’s officially spring (hooray!) I thought it’d be useful to reflect back on my current winter wardrobe – it’s far from perfect and I’m looking to make it better each year. This also gives me the opportunity to plan ahead for next winter and beyond. At the end of this post you’ll find a few last winter outfits I decided to play around with + thoughts on how I can potentially make them better in future seasons.


Please note some links used in this post are affiliate links, which means that I may earn a commission if you decide to make a purchase through them, at no extra cost to you. My intention will always be to inspire you to get creative with what you already have and to create an intentional wardrobe with pieces you’ll love for years to come. Thank you for supporting Her Simple Sole blog!


Her Simple Sole - Winter Knitwear Stack

Winter Wardrobe Purchases

Some notable 2020-21 wardrobe purchases I made this winter include:

Cardigan purchases were a big one this season since I didn’t have very many to begin with. They are truly some of the most versatile pieces in my closet!

Another thing I noticed about most of these purchases is that they can also be worn for Spring/Early Summer/Fall. Meaning, they are not items I had planned to wear exclusively for winter. This contributes greatly to my goal of curating a versatile, timeless, and almost season-less wardrobe. I always mention *almost* season-less, as I do believe certain items are necessary for a well-rounded wardrobe that are meant specifically for a particular season. Think thick oversized sweaters for cold weather and sandals/mules for warmer weather.


Outfit Details: Opal Cardi from Paper Label, Encircled fair vneck tee, Kotn Culotte Trousers, L'intervalle combat boots

Outfit details: Opal Cardi from Paper Label | Encircled Fair V-neck Tee | Kotn Culotte Trousers | L’intervalle Combat Boots (see similiar styles here – most on sale!)


Winter Wardrobe Wishlist

I always stress the importance of creating a wardrobe wishlist and I’ve now just started categorizing mine based on each season. This way I’ll be less impulsive as the seasons come and go. It’s also my way of categorizing wishlist items based on the 5-Piece French Wardrobe approach where the last step consists of adding only 5 statement pieces each season. I touch on this approach here, and plan to reflect more on it in a later post.

After analyzing my sweater collection, I noticed I have several turtleneck sweaters. For the next winter season if I decide to add more, I want to focus on ones with a crewneck or mockneck. Turtlenecks keep your neck warm when you’re braving the cold, but let’s be real – a mockneck is much more comfortable! I’ll also place focus on items made of natural fibers like cashmere and organic cotton.

Some other items more specific to winter that I’m currently eyeing include:


Last Winter Outfits of 2020-21

Here are 3 last winter outfits I put together before even just the thought of wearing knit layers have me sweating in my seat. I’m treating these as visual representations of outfits I would wear again in the future, but with a few wishlist item swaps I’d love to incorporate.


Outfit 1 – Sweater Dress + Blue Jeans + Knee High Boots + Black Coat


Outfit Details: Montpellier Sweater Dress | Denim Forum Yoko Slim Jeans | old knee high boots | old Zara coat

A new way of styling that I’m drawn to lately is a pair of jeans tucked into knee high boots. I would love to replace the slim jeans with a pair of skinny jeans (this would get rid of the bunching around the knee – plus, I always love a good pair of skinny jeans, regardless of what Gen Z thinks!), and replace this old Zara coat with a long black wrap coat that hits right at my calves (I think longer coats are much more chic).

Since a pair of blue skinny jeans is not a winter exclusive item, instead of including it in the list above I’ve categorized it under my “wardrobe essentials” list.


Outfit 2 – Sweater Dress + Sweater Over Shoulders + Leggings + Combat Boots


Outfit Details: Montpellier Sweater Dress | Thurlow Sweater | fleeced lined leggings | L’intervalle Combat Boots (see similar styles here)

I LOVE a sweater-over-the-shoulders look and it’s so great for warmth. But I do find the way I’ve styled it here creates quite a bit of bulk up top when worn with a sweater dress. A lighter knit made of cotton or cashmere (and perhaps in a lighter colour) would help soften the look.


Outfit 3 – Turtleneck Sweater + Straight Leg Jeans + Nude Ankle Boots + Cocoon Coat


Outfit Details: Loft Turtleneck Sweater (old) | Levi’s Ribcage Straight Jeans | L’intervalle Nude Ankle Boots | Aritzia Cocoon Coat

A classic outfit I’d wear over and over. I would love to see this outfit styled with a pair of winter boots for practicality + a long camel coat down to my calves.


Have you ever reflected on your winter wardrobe? Feel free to share – I’d love to hear your thoughts!


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