You are currently viewing My Top 5 Cold Weather Wardrobe Staples

I’m a little over a month and a half into my winter capsule wardrobe and I’ve definitely noticed that I have a few wardrobe staples that I have been gravitating towards.

Perhaps the funniest part is that some of these wardrobe staples are ones that I also wear in warmer weather! Talk about seasonless!

Just for reference, I live in a place that has pretty cold winters. We’ve been hovering around freezing a lot (which has been amazing) but we’ve also had days when the temperature was 6F (-14C) or colder. So layering is a pretty important thing!

In the past, I would retire anything that was remotely summer attire as soon as it got cold out. But some of my favorite pieces are made from silk. I’ve had to find a way to make them work for cold weather.

I think that each of the wardrobe staples that I have chosen for winter would work for a lot of winter climates, with layering as needed. They are all made from breathable natural materials. They are mostly neutral in color and print so they would fit into a variety of wardrobes seemlessly.

The oversized sweater

A flat lay photo of the first of my winter wardrobe staples which is a cream wool sweater. It is folder on top of a folded grey scarf with a beret beside it. My white and  grey cat is sitting on the scarf and looking up at the camera.

This sweater was my last purchase of 2019. And it was well worth it. I had an oversized sweater on my thrift list all through fall and I didn’t have any luck finding it.

When we went to Chicago for our little annual family trip (ok, it’s only been the past 2 years, but that makes it a tradition, right?), I made my usual trip to the Eileen Fisher store.

I tried on a few things but this sweater stole my heart! It check all of the boxes…perfectly oversized (I did size up to get the perfect effect), neutral, natural materials (cashmere, merino and silk blend) and I could immediately think of 3 outfits to make with it.

This sweater won’t be worn through all of the seasons, but it will definitely be a winter wardrobe staple!

It is also important to me that I buy from an ethical and sustainable company when I purchase new and Eileen Fisher definitely checks that box. It was a little on the pricier side (it was on sale and I still paid around $250 USD) but for the amount that I have worn it and will continue to wear it, I am at peace with that!

Check out this post to read about how I clean my wool clothes.

The black jumpsuit

A photo of the second of my winter wardrobe staples which is my black silk jumpsuit hanging over my full length mirror. There is a light wood stool next to the mirror with a grey purse in front of a black purse. My white and grey cat is sitting in fronton the mirror on a cream mat and looking at the camera.

This jumpsuit. I really can’t say enough great things about it. I love it.

I bought this black silk Elizabeth Suzann jumpsuit new last January before she discontinued this style (similar). I had originally purchased it to wear to my sister-in-laws wedding this past June. And it has been one of my all time favorite wardrobe staples ever since.

I have worn it so many times, in all seasons. It is made from silk which means it’s perfect in hot weather but it can definitely be a little chilly when we’re talking about freezing temperatures. That’s definitely when I resort to wearing tights underneath, or my workout leggings if I need a little more insulation.

My favorite way to wear this right now is layered under my oversized cream sweater that I mentioned above. Then I add a pair of brown suede boots to dress it up a little or I add my hiking boots for a more casual look (I’m actually wearing this exact outfit up above with the oversized sweater).

The leopard print dress

A flat lay photo of the third of my winter wardrobe staples which is a silk leopard print dress. It is laid out flat with a black handbag partially o top, a white watch and a pair of black combat boots alongside of it. My white and  grey cat is laying next to it.

This dress is such a chameleon, which sounds like a weird thing to say about a leopard print dress! I wear this over other dresses, under dresses, or as a top! Because it’s so thin, it works under other pieces so well and tucks into pants without bunching, which makes it one of my hardest working wardrobe staples.

I bought this dress secondhand from the Real Real back in the summer. If you’ve been here for a while, or following me on Instagram, you probably know that this is my preferred online secondhand shopping destination. There are a lot of pricey items on there but also a lot of really good deals too.

Let me know if you’d be interested in a shopping tutorial for the Real Real in the comments below and I’ll get one together!

The wide leg pants

A photo of the fourth item of my winter wardrobe staples which is my brown wide leg pants. They are folded in half and hanging at the waist from a pant hanger. There is a chair off to the side with a cream colored throw and pillow in it. My white and cream cat is sitting in the chair.

If you would have told me a few years ago that I would one day be OBSESSED with wide legged pants, my skinny jean loving self would have laughed so hard. Well, I’m not laughing now.

There’s just something about the silhouette that these pants make! Add that to the fact that they are super comfy, and you have the perfect pair of pants. Plus they’re brown, a clothing color that I’ve been very into lately. I’m in love and these will definitely be a spring wardrobe staple as well!

These dreamy pants were actually a gift from Eileen Fisher Renew, which is a clothing take back program that Eileen Fisher does. They take back their gently used clothing and then make these clothes available in the secondhand market through their website. If an item is not in suitable condition for resell when they get it, they rework the material into something new. I think it’s a great program and hopefully something that more companies will begin doing.

The floral dress

The fifth of my winter wardrobe staples which is my floral dress. It is hanging from a door curtain rail. There is a white sheer curtain behind it. There is a clothing rack off to the right side and you can partially see my Burgundy leather jacket.

What can I say about this dress that could describe how much I love it? I waited a year to find it. I first saw it on Hope of @intentionallyhope and immediately fell in love with it.

Then I spent a good 6 months actively looking for it. But I didn’t have any luck finding it. At about the year mark, at a time when I had stopped searching for it, I stumbled upon it on The Real Real and ordered it immediately. It has definitely been that dream closet addition.

A floral dress is something that I didn’t think was “my style” but it’s been fun to step outside of my comfort dressing zone and try some new things.

Whenever I wear this dress, I usually add a pair of 7/8 length leggings underneath for warmth (if I’m wearing brown boots since I don’t have brown tights) or I’ll wear some black wool tights with black boots.


I can say with confidence that all 5 of these items are ones that I will own for years. Some of them will move with me from season to season and some will be put away and eagerly pulled out at some other time.

I’ve been conscientious of my clothing consumption for about 5 years now, and actively pursuing “slow fashion” for about 2 years. But the concept still feels “new” to me. Perhaps it’s because it’s taken me this long to finally figure out my personal style and what works for me. Having items that I am excited to wear and will love for years is still new to me but I’m thankful to finally be in this place.

If you’re at a point where you’re unhappy with you’re wardrobe and you’re looking to change that, it will happen. It just takes a little time. I’ll be right here to cheer you on!


With all of that being said, I’d love to hear about the items that you’ve been reaching for over and over this winter? Will they move with you into the next season? Will you store them away and then “shop your closet” next winter?

Until next time,

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This Post Has 4 Comments

  1. Rita

    Just wanted to say thank you for continuing to post on your instagram. I don’t have instargram so I can’t comment there. I live in Norway and as in so many other places, we are told to mostly stay indoors and to work from home. So the days are pretty long and the internet is full of mostly corona-news. So thankful for the Little bit of distraction you give, and the reminder to keep living as usual wherever possible, I guess that is something we all need now.

    1. Gillian

      Hi Rita!! Thank you so much for your kind comment. I am so happy that I can bring a little light into your day. I have wondered if I should or shouldn’t post during this time and your comment helps to affirm that I should. Thank you!! I hope you find as many joys as possible in your home over the next little while as we get through this together ❤️

  2. Jennifer

    Hi Gillian,

    Yes, I’d love to hear about how to Shop at the Real Real…I need the tips on how to do searches, etc.

    1. Gillian

      Thanks for your comment Jennifer!! I will start working on a post so stay tuned 😉

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