In Discussions, In my closet, Shopping, Style

Curated Closet Workbook Exercise: What’s my clothing message and confidence?

Subconsciously or not, our clothes send a message about who we are, our values and personality. What message does your current look send? What message would you like it to send?

My current look:

Powerful, confident, luxe, understated yet whimsical (fun/cheeky), stylish but not trendy, and crisp.

My preferred projected look:

Exactly that. Not fussy, not uncomfortable, not disjointed.

I like having fun with clothes and doing SOME trendy things like distressed jeans and skinny jeans (are they still considered trends, or are they staples now?), and wearing marble-printed shirts, or a furry faux fur stole over a tee…

But I still want the overall look to be luxe, powerful, and COMFORTABLE.

Ain’t nobody got time to be uncomfortable.

But once in a while, I wear heels!

Imagine you had total confidence (and unlimited funds to overhaul your wardrobe). Would you keep wearing the same type of outfits as you do now? If not, what would you change?


Do not tease me.

I would keep wearing the exact same type of outfits, but my brands would be jacked up to have MORE luxe designer and obscure labels, like The Row, Amour Vert, Joie, Theory, Smythe, Sentaler, Roksanda, IRO, Scanlan Theodore, Sézane, Mansur Gavriel, and so on.

I’d be wearing so many different pieces that are basics but in much more luxurious fabrics.

More of these Smythe jackets for instance!

I do all of the above today, but it is harder because I am scouring secondhand or thrift, and in good to excellent or new condition IN MY SIZE AND COLOUR for a decent price.

Very hard.

It would be easier if I just had lots of money to just buy everything at retail.

As it stands, I am using Banana Republic or Massimo Dutti as the main staple of my wardrobe for basics like tops and some fun skirts, even jackets.

I’d scrap them completely and just go Equipment for basics, and more designer brands Milly for the fun skirts, The Row or Armani again for high rise pants…


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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  1. Flo

    You point all the time you are ‘very type A’. I’m curious why ?
    Type A people were said to be hasty, impatient, impulsive, hyperalert, potentially hostile, and angry (wikipedia).

    1. Sherry of Save. Spend. Splurge.

      Yes, I am all that. 🙂 But Type A people are also very detail oriented, fast at getting things done, decisive and perfectionists.


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