In Discussions, In my closet, Shopping, Style

Curated Closet Workbook Exercise: Can I repeat outfits? How do I shop?

What is your stance on repeating outfits?

I can repeat outfits, but not days in a row.

Are you okay with wearing the same head-to-toe look twice in two weeks?

Nope. I can’t do it unless I am depressed or tired, and then I don’t really want to wear anything but the same thing over and over again.

I remember a point during the summer when I was home with Little Bun (then, Baby Bun), and man…. he broke me.

He broke me to the point where I just wore the same stretchy dress for weeks at a time. I only snapped out of it once readers and friends starting expressing concern because they all knew how much style and all that meant to me, so for me to just give up… it meant I had snapped in some way.

It is not a good thing when I repeat outfits in a row. It is fine if I re-wear a similar look the next week or change out the top or something, but not if it is exactly the same day in day out.

How about individual pieces?

This one, yes! I wore the same top within a span of 2 weeks because I wanted to but with different skirts, a belt…

What is your typical decision-making process when it comes to buying clothes? Do you often buy things on a whim, or do you tend to make sure you have compared all your options first?


I buy things I like on a whim, like that trench coat skirt above. I saw it, knew it was on my bucket list for years to find a trench coat skirt (I had been eying Burberry all of this time), and when I saw it at Massimo Dutti, my size had already sold out, so I took the size up and had it tailored down.

If it is something like a staple however, like a shearling coat, I go through all of the options — what colour? what brand? should I go with a cheaper option because it is just a trendy piece? would it look too fake and cheap?… and then I make a decision, which is how I ended up with this Acne Studios shearling coat:

I wear it to death during the winter when it doesn’t snow.

It is SO warm and comfy, I cuddle up in it…. I do not regret this purchase.

What is your typical shopping strategy? Do you prefer spending your budget on fewer, more expensive clothes or do you tend to spread it across lots of cheaper items?

When I was younger, I preferred to spread it across a lot of cheaper items, because I thought MORE was MORE.

I wanted all the tops in all the colours for $5 each.

Nowadays, my budget has expanded quite a bit (low 5-figure spend per year on clothes), and the pieces have diminished.

I am spending more, and on secondhand designer items, and I have less pieces than if I used the same budget when I was younger.

Quality, expensive, and luxurious are meant for MOST of my pieces, and I try to buy secondhand as much as possible. For instance, the jacket below is Dior, but secondhand and I scored it for $150:

Or I tend to buy really special pieces like these two dresses, under $100 each, originally retailing for much more.

The first one on the left is Alice and Olivia that retailed for $350 USD, and the Erdem dress on the right is a custom Erdem print I got for under $100:

These dresses are not your run of the mill floral dress – just look at the impeccable detail in the print, the depth of the florals… and the fact that it is made out of luxurious fabrics like silk and cotton.

I only go to mainstream brands for things like white collared shirts or tees that discolour quickly (makes no sense to keep wasting money by replacing them every 3 years). I had purchased a great white Equipment silk shirt for $300-ish but it is already starting to look worn, 3 years later.

Now I am trying out mainstream brands like Massimo Dutti and Banana Republic for similar white shirts (not in silk) and using them instead.

That said, if I feel like the quality is there, and it looks good, I will buy it like this Gap rail stripe shirt for $30 that I felt looked much more expensive, and more like a $500 Nili Lotan top:

I focus on the pieces, regardless of price, and then decide what I would pay if it were retail.


Interested in reading more?

Flip through all of my Curated Closet Workbook pages and notes.

A little about this series:

I am embarking on a 8-week (or longer) excursion to do this exercise from one of my favourite style books – The Curated Closet – and to show you what my Curated Closet Workbook (companion workbook to the actual book) looks like at every step of the way.

Why do this?

Because I know what I like but I have no idea why I like what I do. I just do, and it seems very hodge-podge and all over the place. Being very Type A, I kind of want to pin it down and to know WHY.

I feel like it would help me narrow down my style personas more, and stop me from making bad / stupid shopping mistakes.

Also, I really like reading about these kinds of things from other people. I love it when people go through and talk about their style evolution and why.

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Sherry of Save. Spend. Splurge.

Am my own Sugar Daddy. Am a millionaire at 36 after getting out of $60K of student debt in 18 months, a little over a decade earlier, using I have worked 50% of my career (taking 1-2 year breaks), and quadrupled my income within 2 years of graduating, going from $65K to $260K with an average lifetime savings rate of 50%. I have 11 side incomes that are on track in 2020 to make me $50K - $75K. I could retire today if I wanted, but love my work-life balance as a freelancing consultant in STEM (Science, Technology, Engineering, Math). I am all about balance - between time and money, and also enjoying my money. I also post daily on Instagram @saverspender.

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Posted on May 24, 2017

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Save. Spend. Splurge.
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