You’ve probably already over-scanned your Spotify Wrapped by now (yes, you really played that Taylor Swift song this several times), but let me introduce you to another idea: an annual summary of your wardrobe. I wish my closet had its own algorithm to do this for me, but every year I like to take a look at the most worn pieces in my closet because it helps me dictate exactly what purchases in are worth and how to be a better buyer next year. Since I already constantly share my shopping finds, I thought it would make more sense to share the best items I’ve worn this year. I promise it’s not as repetitive as your group of friends’ musical choices.
From my favorite J.Crew cashmere sweater to my now-beloved Staud bags, I’ve really put the items below through their paces. They accompanied me on simple office days and trips around Europe, and I will take them all with me in the new year. Keep scrolling to shop my recommendations, and don’t forget to create your own holiday wardrobe favourites.
I’ve worn it once a week in spring and fall, it’s just the perfect lightweight jacket.
These pants have always been a bestseller among our readers, and after trying a pair on my own, I can see why. They are light and drape over the leg in a perfectly relaxed way. I bought the normal size, but I would go for the small version next time.
I’ve had many luxurious suede bags on my wish list, but many of them were too close to the $1,000+ mark for my liking. This one has exactly what I wanted – it looks more expensive than it is, is comfortable on my shoulders and fits everything I need.
Coach has mastered the Y2K resurgence, but its line of sleek ’90s bags is just as worth the hype.
Biker jackets can cost a pretty penny or completely ill-fitting, and this one fits everything on my checklist.
After seeing this dress all over my Instagram, I finally made the purchase and have no regrets. This is the most flattering dress I have ever worn.
If you’re new here, I’m a Staud superfan. The Moon bag is one of the brand’s most coveted pieces and for good reason. It is versatile and always has a unique shape.
Comfort is a big priority for me, and when I picked these up at a Kotn store in Montreal, I knew I needed them in my wardrobe. I wore them on my six hour flight to London and slept like a baby so the comfort factor is definitely there.
I borrowed my brother’s Fear of God hoodie on a family trip and was about to steal it. He ended up gifting me mine, and it became one of my most worn comfy pieces.
Another Staud bag, are you surprised? While the Moon bag makes more of a statement, I kept this one as an everyday staple.
Twenty-twenty-two was the year of avant-garde fashion, as pop-punk and gothic aesthetics made a resurgence. If you’re looking to add a moody touch to your look without spending a ton of money, this Mango bag is ideal. It’s lightweight and fits comfortably on your shoulder, and people almost never believe me when I tell them where it’s from.
These boots may look intimidating, but I promise they’re more comfortable than you think. They give a great amount of extra height without too much pain.
It may surprise you, but I’ve never owned cashmere until I tried this J.Crew option, and it certainly set my expectations for knit style at an all-time high.
Every time I wear them, people ask me where they’re from. They are perfectly tapered at the waist and reach to the ankle.
I always thought I wasn’t layering enough, but it turns out I never got the right coat. Aritzia’s baggy coat became my saving grace for the harsh winter days we had. Not to mention its design is chic so no matter what I wear it always looks great. It’s a win-win situation.
It seems like these ballet flats are almost always on sale, and more people need to take advantage of them. They’re comfortable, look expensive, and come in both classic black and yummy red which I own both. With the ballet trend, there are tons of options on the market, but this one is one of the best.
I understand this set is pricey, but it really is one of the most comfortable sets I’ve tried – and I’ve tried many. I wore it on Thanksgiving and was able to relax happily with its comforting stretchy waistband. The pieces are versatile, so you can mix and match them with ease.
While some people can outgrow heel pain, I absolutely cannot. So after trying on many stiletto boots and wincing in pain, I was extremely happy to find this pair from Vagabond. Block heels can look a little clunky, so I love how this one is slightly thinner and angled, which gives a unique look. I’ve worn it for walks around New York and always come home pain free.
Next, 10 easy, comfortable and trendy winter outfit ideas