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Outfit Diary #5
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Outfit Diary #5

I've dubbed this the "Week of Color" - what started off unintentionally became the theme I got dressed by!

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Gillian
Dec 29, 2024
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Outfit Diary #5
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It’s hard to believe that the last full week of 2024 has ended. It was a year of ups and downs for me, as I’m sure it was for a lot of you as well.

I learned a lot about myself, some good and some bad. I let myself down a lot but I also bet on myself a little more. I stepped out of one challenge and into another.

I feel ready to head into 2025 with the lessons that I’ve learned over the past year, and with some personal and professional goals that I’ve set for myself, especially the low buy year. I’m excited to see where the year takes me!

How about you - how was your 2024 and what plans are you excited about in 2025?

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In yesterday’s newsletter, I explored the idea of The Hunter vs. The Curator. I’ve spent most of my life being a hunter and I don’t think I’ve ever really enjoyed my wardrobe, or the process. The constant searching, followed by the influx of items and the subsequent decluttering have made me feel anxious and out of control.

And for someone who likes to feel a sense of control, this has caused a lot of stress for me. I really believe that these weekly outfit diaries are helping me to move away from all of that and toward becoming more of a curator.

Something that’s been coming up for me again lately is my issue with clothing attachment - in the past, it’s been sentimental but I have worked to overcome that mostly.

Now, it seems to be more centered on “missing out” on all of the outfits that I could make with a certain item. But I’m trying to remind myself that it doesn’t matter how amazing an item is or how many great outfits I can make with it if I never actually wear those outfits. This is a trap I fell into a lot when I used to post my outfits to Instagram that I am still trying to wiggle my way out of. That’s definitely a focus for the coming year.

And probably a future newsletter - I already wrote the title ;)


All 7 days worth of outfits are reserved for paying members of the community. However, the first 3 outfits in this newsletter are available for all subscribers.

If you are finding value in my newsletters and would like to support my work, you can become a paid member of the community for $5 per month (an annual subscription for $50 gets you 2 months free). This gives you access to the full weekly outfits post, all of the archive and anything else that I post.


Outfit Rating System:

Comfort will refer to how comfortable the outfit was on that day. The questions I will be asking myself: was I too hot or cold, did it fit me properly, did I have to adjust any of the items constantly?

Style will be based on how I felt while I was wearing the outfit. Did I feel stylish in the outfit, did it feel like a “me” outfit, or was there something about it that was off?

Fun will refer to how playful the outfit felt. Did I try something new, was I really excited about the outfit, or was I bored by the outfit?

Each category will be rated out of 10.

* I have not added any links to items. Most of the clothes I own are preloved or old and it is never my intent to encourage you to shop, unless it’s your own wardrobe - I STRONGLY encourage that! However, if you see an item that you’d like more information on, leave a comment or send me a message! If there is a link, it’s just fyi, not affiliated.


Sunday - Purple

OK, when I say the week started off with a bang, I really mean it - I LOVED this outfit!

I felt so cool and stylish.

I don’t think I’ve ever told you the story behind this coat, and if I have, sorry, here’s a refresher:

It was probably 2022, or maybe it was early 2023, and I was in one of my favorite antique stores. There was a circular rack with some clothes on it and I spotted some purple suede sticking out. I had never been one for purple clothing but vintage suede and leather are my kryptonite!

I pulled it off the rack and had one of my kids hold my handbag and the coat that I was wearing. I tried it on and felt like Cinderella - it fit perfectly. And it was $25!

As I was walking away from the rack and heading to the counter to pay for it, I heard some college girls talk about how nice it was and “lucky her” and I just felt so fortunate to have found it.

When I got it home, I threw it in the washing machine and she cleaned up very nicely. If you feel terrified by, or interested in, washing suede in the machine, I have a highlight on my Instagram page called “Clean It” where I have documented my leather/wool/suede cleaning adventures!

Back to the outfit…

On Sundays, we have a family outing and we usually go downtown for a treat and to look around. It was a little chilly but I didn’t want a big coat, so I relied on layers to keep warm.

I started with a base outfit of a merino wool mockneck and black utility pants. I added my vintage quilted vest as an extra layer before putting on my purple suede jacket.

And I can’t go anywhere without a beanie at this time of year - as soon as it’s below 40F, I live in them!

I took advantage of the fact that it was dry outside to wear my tan suede sneakers. I found these cute sheer flower socks in my sock drawer and I think they added a little “fun” to the look, even if you couldn’t really see them - I added a pair of trouser socks underneath them because I was afraid that my feet would get cold with just the sheer ones!

Comfort - 10/10; Style - 10/10; Fun - 10/10.

Monday - Dark Green

These are a pair of Pomona Pants that I made in 2020 or 2021. I wore them a little when I first made them but not a whole lot since then. I recently took them down out of storage as a sort of “last chance” to wear them or else they need to move on.

I think that I struggle with the color and finding things to style them with. It doesn’t seem like it should be that hard. I think I need to experiment with them and see if I can find some items that they work well with.

I’m trying to move away from the thought that every item has to go with every other item in my wardrobe - some things just don’t work together and I need to find a few items that I can wear with these pants that I feel good in!

When I woke up on Monday, I decided that I wanted to wear them which was a bit stressful because I didn’t have a lot of time to get ready before I had to leave and I wasn’t liking the tops that I was trying on with them.

I eventually settled on my “Kaya” sweater. I think the slightly oversized fir of the sweater and the length really work with the proportions of the pants.

I have always really liked how chunky boots look with wide leg pants so I wore my old Ganni rain boots. They almost look like black boots since the pants are so wide and nearly cover the entire boot.

It wasn’t too cold out this morning so my checkered wool coat completed the outfit nicely!

Comfort - 10/10; Style - 10/10; Fun - 8/10.

If you’re ever interested in making your own pants, the Pomona Pant pattern is a really great beginner-friendly one!

Tuesday - Red

My whole goal with Tuesday’s outfit was to wear my red leather jacket because if you can’t wear a red leather jacket on Christmas Eve, when can you wear it??

Since the jacket was going to be the statement item of the outfit, I wanted to keep the rest of the color palette neutral. I love how grey and red look together so I opted for a grey cashmere sweater to go with my wide leg black pants. Under these two items, I wore a base outfit of a tank top and a pair of leggings.

I’m a big proponent of the french tuck and will usually go with it but after trying this sweater tucked and untucked, I opted to leave it untucked and I think it worked better with the length of the jacket.

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My black Moto boots seemed like the obvious choice for this outfit and I even added a handbag this day.

I used to be really into handbags. I thought that they completed every outfit. But more and more lately, I’ve been leaving them at home and opting to throw my items in my pockets instead (I usually only take my phone, which has a wallet attached for my cards, a lipgloss and my car keys).

I think this is just a bonus of winter and big jackets. I do use a bag in the summer, but it’s usually just a tote bag. With these realizations, I am planning to reduce my handbag collection to just a handful this year.

Comfort - 10/10; Style - 10/10; Fun - 9/10.

It was on this day that I noticed that I was wearing more color than usual so I decided to lean into it for the rest of the week!

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