The men in my household appear to wear one pair of pants for all occasions. It has become a running joke/concern among our friends that my husband hasn’t changed out of his navy Bonobos pants in months. My older son feels it’s appropriate to always wear his slouchy parkour sweatpants. I guess you never know, though, when you might need to parkour your way out of a fancy restaurant or black-tie wedding. My younger son is the closest to me in terms of fashionista demands, but most of 2020 has been experienced in his hand-me-down blue velvet pants from Pax. Admittedly, they feel luxurious and look fabulous.
Capsule Wardrobe Inspo: My 12 Most-Worn Winter Outfit Pieces
I am realizing that I’m not that different from my guys…especially in winter. It was ridiculously easy to look in my closet and pull out my most-worn items — the pieces I wear on the daily over and over and over, the ones I reach for without even thinking for all different occasions. These are the pieces people are probably sick of seeing me wear, but I don’t care because they really are my winter outfit workhorses.
If you haven’t done this exercise already (I did it last year here), I encourage you to take a few minutes to look at your most-worn outfit pieces this winter. It has been really useful for me in determining what pieces I may be willing to spend more money on in the future or what higher-priced pieces I want to search for during the end of winter sales.
**Note: MANY Items From Categories Below Now On Sale**
1. A Boxy Sweater
I actually have two Everlane boxy sweaters (dark navy and gray) that are in CONSTANT rotation right now. With denim, with black pants, over my workout tights, and even over my jammies cuddled up on the couch — these sweaters are delicious! I once said that cashmere was too hot and itchy, but turns out I just wasn’t wearing the RIGHT cashmere. The boxy cut is the one that I’m most drawn to right now—easy, but not boring, and the Everlane one comes in a ton of colors.
Shop More Boxy Sweaters
2. A Soft Drapey Top
This winter I am ALL about things that are soft, and this drapey gauzy top from Madewell meets my requirements, while also being versatile enough to dress up or down. Most sizes sold out, but lots of similar options below…
Shop More Drapey Tops
3. A Playful Tunic
I am such a tunic fan — they may waver in the “Current Trends World,” but I love them and will wear them…ALWAYS! My Free People tunic that I got during the Nordy Sale has gotten SO much use, but sold out fast. Several other similar options are available, though. One of my other most-worn items is a shift dress (not officially a tunic, but I wear it as a tunic). I wear these over black cropped pants with heels when I need a bit of a dressier look, but don’t feel like wearing a typical dress.
Shop More Tunics & Dresses (That I Would Wear As Fancy Tunics)
4. A Cute Puff Sleeve Top
This has been my go-to this season for taking my look up a notch just slightly…I mean it IS still a t-shirt. The puff sleeves do wonders, though, for an otherwise boring outfit. My top sold out, but there are a bunch of similar ones below.
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5. An Easy Striped Top
A striped top is always one of my go-tos, whether it’s in the form of a tee in the summer or a sweater in the winter. Easy to wear, but never boring. My current striped top is an old one that I wear with all the denim in my closet, as well as pants and skirts. When I’m looking in my closet feeling like I have nothing that is quite right to wear for the day, a striped top is often my answer.
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6. A Small Bag For Your Big Bag
I’ve started carrying this small belt bag (with my most important items) with me every day inside my Boss Bag. This belt bag, in particular, is fantastic because it comes with interchangeable straps — although I do use the belt bag strap almost exclusively. Perfect size for carrying my small wallet, lipstick, keys and sunglasses, and then I just grab it out of my Boss Bag for quick errands or a night out.
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7. Versatile Cropped Black Pants or Jeans
Okay, I cheated. These are actually two of my most-worn items that I squeezed into one category to make everything fit into a Top 12 List. I wear my cropped flare denim in washed black ALL the time, but I get a ton of use out of my black cropped flare pants as well. I wear the jeans and pants interchangeably with tunics, soft tops, boxy sweaters and shift dresses. I just switch them out depending on if I need a more professional/dressier look.
Shop More Black Denim & Pants
8. Comfy Light-Ish Blue Denim
I have several light-ish jeans that I love (like these MOTHERs and these Perfect Vintage Madewells), but these Cali-Demi Boots below are the ones I reach for on the daily. They’re soft, a great wash, fit really well, and have the look of a stiff denim without the feel–they’re super stretchy.
Shop More Light-Ish Blue Denim
9. A Carry-All-The-Stuff Black Bag
Shana has this in white (which I adore), but the black is more versatile for me. Both colors are on sale. It fits my laptop, my dance shoes, a huge water bottle, my coffee mug, kids’ snacks, my small belt bag and more….and still manages to look stylish.
Shop More Black Bags
10. Walkable Clog Boots
You guys know I love my clogs, and they’re not going anywhere. Mary Jane clogs in the spring, clog sandals in the summer, slingback clogs in the fall, and clog booties in the winter. Walkable, wearable and wonderful!
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11. Fresh, Light-Colored Booties
These booties have been my favorite addition to my winter closet this year and have totally changed up many of my go-to outfits. It’s amazing what switching out a dark bootie for a light bootie can do for a look. These Day Glove Boots, in particular, are really comfortable. I don’t exactly know how they’re so comfy, because they don’t have my usual comfort shoe cushioning. Magic, I guess. Whatever it is, it’s working because I wear them to walk the whole city.
Shop More Light Booties
12. Cool Black Fashion Sneaks
The vibe is perfect on these. Not quite “dad-sneaks” (I can’t pull off that amount of trendiness), but they still feel current and fresh. I would love to add the cream ones to my rotation because I’ve already gotten a ton of use out of the black ones.
Shop More Cool Black Sneaks
If you have a second, let me know some of your most-worn winter pieces — your true workhorses — and I can help search for them in the upcoming sales!