Winter Wardrobe: What Ill Be Wearing

A new season is here and that means its time for an update on whats currently hanging in my closet. I dont follow a strict capsule wardrobe anymore, though I still use a lot of what I learned from when I did follow the rules. Meaning, I try to keep a small wardrobe of items that mix-and-match easily.

I may add a few items throughout the season, but I try to be mindful about what I add to my wardrobe as I find having fewer options makes getting dresses easier (and its better for my wallet and the planet). I also pay close attention to what items are no longer working for me and I pass them so they can continue to be used and loved by someone else.

These days, Im preferring a more streamlined wardrobe than I was last year at this time (I was doing more of a year-round wardrobe). So, Ive packed up even more of my off-season items to put away for a few months until the weather warms up again to reduce the noise in my wardrobe.

When I shared my Fall Closet post, I split the items into two categoriesprimary and secondary. I liked that set up, so I continued that for this post.

The primary items are the ones that I wear regularly. Some are old favorites, some are newer items Ive added as my style has evolved. But these are the 36 items I know Ill wear again and again. I could be content with just these hanging in my closet.

The secondary items are the ones that I really like, but dont reach for as often. Maybe theyre a little harder to style or arent quite perfect for the season, but are a fun way to mix it up every so often. For example, during winter my short sleeves are in the secondary category. Every so often Ill wear them as a layering piece, but they arent in my weekly rotation.

While this is a pretty complete list, there are a few things I havent included: my weekend athleisure gear (leggings, joggers, etc.), workout gear, pajamas, a few basic tank tops and tees, and outerwear. I also have a couple of pairs of shoes that I really only wear once or twice per year, but am still hanging on to (for now).

As always, Ill be sharing how I wear these items over on Instagram, so I hope youll follow along.

Heres a look at what Ill be wearing this winter (and most likely, well into the official spring season).

winter 2020 capsule wardrobe


Striped turtleneck (c/o Tradlands, large, 2019): After years of not liking to wear turtlenecks, I have fallen back in love with them. I love this oversized, striped version fully tucked into black jeans or wide leg pants for work just as much as I like it with leggings and a jean jacket for weekends.

Long-sleeved tee (c/o Kotn, medium, 2019): I just received this basic long sleeved tee thanks to Kotn. It is a thick, quality tee with a good amount of stretch. I would say it runs a bit small as the medium is quite fitted on me.

Raw silk T top (c/o Jamie + the Jones, small, 2017) This was my first umber/rust colored shirt and Ive never looked back. The T Top is always something I reach for when Im not sure what else to wear. It really makes a statement, even when paired with basic jeans, so I dont have to put in a ton of effort.

Brown turtleneck (c/o Kotn, medium, 2019): This is another new addition for winter. This doesnt have as much stretch as the long sleeve tee (in fact, its kind of hard to get over my head), but I like the quality feel of it. This will work well with wide leg pants or layered under cardigans or blazers thanks to the fitted shape. I think this also runs a bit small as the medium is very fitted on me.

Raw silk T top (Jamie + the Jones, small, 2017): One of my favorite outfits is this top paired with black denim and statement shoes. It works both casual and slightly more dressy.


Graphic sweatshirt (Tradlands, medium, 2019): I love a cute sweatshirt for casual days at work or weekends when I want to be comfy, but not looks sloppy. I love the colors, fit, and brand, so this sweatshirt is a new favorite.

Black sweater (c/o Vetta Capsule, 2018): Vetta just re-released this sweater in time for fall! The details make the sweater: turtleneck is detachable (with buttons), there is a cute side zipper, the oversized knit stands out, and there are thumb holes. This was one of my more worn items last winter and I know that will be true again. I did wash this sweater a few times last winter and it held up great.

T Sweater (Jamie + the Jones, medium, 2016): An old favorite, Ive blogged about this sweater twice and have worn it nearly 50 times already. I cant imagine a fall/winter wardrobe without it. Its so cozy and such an easy piece to throw on and go, but I always feel great wearing it.

Fisher sweater (c/o Tradlands, x-small, 2019): I love that this sweater is 100% cotton because wool doesnt work well for me. Tradlands just released more colors in this style and theyre so good. I love to wear this with simple jeans and cute boots on a cold day.

Fleece Sweatshirt (c/o Everlane, medium, 2019): I have primarily been wearing this after work and on weekends (if you follow along on IG, youve seen it nearly every weekend in my stories). I love the idea of incorporating it more with my work pants and wearing it to school this winter.

Gray Sweatshirt (Old Navy, 2013?, similar, similar): Similar to the fleece, after doing a style series video with this plain gray sweatshirt, I decided to put it more in the forefront of my wardrobeyes even for work.

Crew neck sweater (c/o Everlane, medium, 2019): I was initially drawn to the texture of the knit on this sweater. Once I tried it one, I also loved the softness and fit. I like that this sweater can be tucked (unlike me T Sweater), so it will work well with wide leg pants on cold days.

Convertible sweater (c/o Vetta Capsule, 2017): This is another genius Vetta style, that can be worn with or without the turtleneck and with the buttons forward or backward. Its more oversized, so it looks cute with fitted bottoms and feels super comfy.

Slim turtleneck (Brass Clothing, large, 2016, updated version): I didnt wear this turtleneck much last year, but I have a feeling that will change this winter. Heres a look at a few ways to wear a basic turtleneck.

Donegal cashmere (secondhand Everlane, medium, updated version, 2017): This sweater can be hard to wear because its very cropped. But I love the flecks of color and texture, so I save it for days Im wearing very high-waisted bottoms. Its a classic that I know Ill wear for a long time.

Convertible cable knit sweater (c/o Vetta Capsule, small, 2019): I love Vettas creativity and that this is three sweaters in one (a turtleneck, a crew neck, and a cardigan). This is the kind of piece that I reach for again and again because it makes a statement without requiring a lot of work.


Coatigan (Madewell, small, 2018, love this years verion): In the past Id tried a few different longline cardigans, but I never felt they looked great on me. I love the more structured style of this jacket and the interesting color. This will be a great fall jacket, but I also wore it to work quite a few times as a cardigan.

Sweater blazer (J.Crew Factory, small, 2019): This was a late spring addition last year and I love it. I love the look of blazers, but they also felt a little hard to teach in. This one is 100% cotton, which makes it feel more causal, but it also moves more easily. I cant wait to wear this a lot more this year.

Denim jacket (hand-me-down H&M, 2019, similar): A few years ago I purged all of my denim jackets because I just never wore them. I borrowed this one from my sister last spring and never gave it back. I wore it all the time. Its a perfect completer piece to an outfit.


Leopard Print Dress (c/o Sonnet James, small): This bold (for me) dress has quickly won my heart. I have worn it multiple times already and did a styling video to show how versatile it is.

Wide leg crops (Everlane, size 6, 2017): This was my first pair of wide leg pants and Ive added a few pairs since.

Black denim (Everlane, size 27, 2017): I moved these from my secondary fall list to my primary list for winter since I seem to be reaching for them more this year.

Wide leg denim (Everlane, hand me downs from a friend, size 28, 2019): I was so excited to get this pants from my friend, Andrea. At the time they were a special release Everlane style that I had missed out on, but now they have a very similar style regularly listed. They make such a statement that even with a simple tee or tank I feel pulled together.

Tencel pants (c/o Only Child, medium): Coming soon, but I am so excited to share more about this brand Ive admired from afar for years.

Crop flare denim (hand-me-downs from a friend, similar): I dont wear these all that often, but its fun to have a different cut in my wardobe to mix things up a bit.

Straight Leg Crops (Everlane, size 6, 2019): I love this rich, warm cocoa color. I tend to get into ruts with my pants (eh hemstraight leg jeans and wide leg pants), so Im excited to mix it up this year.

Medium wash denim (secondhand Madewell, 2017, similar fit): Old favorites. The fit and color is very straightforward, which I like for blue jeans.

Washed black denim (Everlane, size 28, 2018): I wear these about once per week to work. These are my most comfortable pair of denim. Another of the cheeky fit, they arent too loose or too tight and the denim is super soft.

White denim (Everlane, size 28, 2019): A great contrast from my usual black pants. I love the cheeky fit because they just skim my body and dont feel to RHOC.

Black wide leg pants (Whimsy + Row, 2018): These are a nice alternative to my black denim for work, so I wear them every other week or so. It has taken a while to figure out how to best style wide leg pants on my short frame. I feel like I made a lot of progress last year, so Im more confident wearing them than ever.


Leather Sneakers (c/o Everlane, run a tad snug, 2019) // Snakeskin boots (Poshmark, 2019, similar ethically made, similar) // Classic clogs (Lotta From Stockholm, run big, 2017) // Suede heels (Everlane, tts, 2018) // Mules (c/o Nisolo, tts, 2018) // Heeled boots (Nisolo, sized up one full size, 2019)


Graphic Tee (c/o Ramble and Co., XS/S): A great layering piece for fall and winter, but something that Ill wear regularly again until it warms up. I like to keep out a few favorite tees to wear under cardigans and blazers through winter and this is one of them.

Boyfriend cardigan (Old Navy, medium, love this updated style, 2017): I feel this cardigan is starting to look a little worn out, but I dont wear cardigans enough to warrant investing in a new on at this point.

Pencil dress (Brass Clothing, large, 2017): This one takes some courage to wear, so I dont wear it super often. It works well for work and dress up depending on the footwear, so Ill hang on to it for a long time even if it isnt in regular rotation.

Green midi skirt (secondhand Madewell, 2019, similar): This skirt will show up for in fall than winter, but Im hoping to get a few good wears out of it before its time to pack it up.

Leopard Oxfords (secondhand Target, 2016)

Pima cotton tee (Everlane, 2019): I like to keep a couple of more fitted tops to wear with my wide leg pants. Since Im short I find the wider bottoms look better when I balance it with a fitted shirt. This deep red is perfect for fall and winter. The pima cotton is thinner than most of my tees, so I like that is doesnt add too much heft under other layers.

Reversible Jumper (c/o Vetta Capsule, small, 2018): I tried this a few times last year with shirts and sweaters layered underneath and I just didnt care for it. But early in fall I dont need tights can wear it with an outer layer, so it will stay in my closet a little longer.

Raw silk top (made by a friend, 2019): My friend, Jaana, made me this raw silk top after I admired a similar one shed made for herself. I chose an off-white to compliment my green skirt and rust pants. I love the lose fit and perfect drape when its tucked.

Dorsay Oxfords (Nisolo, tts, 2017)

Girlfriend tee (Tradlands, medium, 2019): Fall is usually pretty warm (until its suddenly not one day), so I always keep a few favorite tees out to wear during the transition. I had the original version of this tee and recently sold it because it ran a little small across the shoulders and chest. I recently bought the updated fit and its perfect.

Raw silk tee (Two Fold Clothing, medium, 2017): I love wearing this tee on its own, but the color and texture also make it a great layering piece.

Ponte Pants (Brass Clothing): A couple of years ago I wore these pants all of the time. Then I started to move to styles that had more room and werent skinny cut. These are high quality pants, and I may get back into the skinny fit again, so I keep them and wear them every so often.

Heeled mules (c/o Nisolo, tts, 2018)

Tapered pants (c/o Vetta, medium, 2018): I ignored these pants almost all last winter. Finally I tried them with my heeled Chelsea boots and I was hooked. I look forward to wearing them a lot more this year.

Boxy Tee (Everlane, medium, 2019): Is any core wardrobe complete without an easy basic tee? I love the softer color and slighly forgiving fit of this tee. It works well with jeans and clogs for a classic look. But its also an easy pairing with my wide leg pants, which I find harder to style sometimes.

Light Wash Denim (secondhand Madewell): Last year I just didnt reach for these jeans as often as I had in past years. The super light denim doesnt look good with my darker winter shoes and boots, so I keep them more for warmer weather.

Cardigan (Express, 2015): I dont necessarily love this sweater, but I dont dislike it enough to purge it. Every couple of seasons I wear it a handful of times and that warrants keeping it. I sometimes wear it with leggings around the house, too.

Jumpsuit (Old Navy, medium, 2019): Though this item is very summer-y, it is also very easy to wear with different layers, so Ill be keeping it in my closet year-round.

If youre considering building a capsule, or just trying to figure out what a smaller wardrobe would look like, I hope this helps give you some ideas or makes it feel more feasible. In the beginning I feel like I was always looking for a formula to create my capsule, but I think the best approach is to really start by identifying what you love to wear and getting rid of (or packing up) all of the items you feel just meh about.

Once I realized how great it felt to have a closet full only of items I love wearing, I knew Id never go back. Heres a post on my wardrobe history if youd like to see where I started. I also have a drop-down menu of all of my old capsules if youd like to see the progression.

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