In Discussions, In my closet, Shopping, Style

Curated Closet Workbook Exercise: Styling my outfits & my comfort factor

Do you want people to notice your clothes?

Yes and no. Yes in a good way, like “Hey I love that skirt”… or “Those shoes are amazing”.. but not in a bad way where I get negative or uncomfortable attention.

Really though, I dress for me. I don’t care if people like what I wear or not, I LOVE colour, I LOVE style, I LOVE wearing what I wear and it boosts my morale, mood and confidence.

My partner sometimes eyes me like: You are wearing leather leggings to the grocery store? Are you for real?

He knows better than to say anything, but it is not what he would have chosen if he were a woman, if that makes sense.

He actually doesn’t care about what I wear as long as I am happy, and as long as I am comfortable, he only cares that I feel comfortable.

Overall, how comfortable were your outfits?

I would say 7 out of 10.

I mean, if I am belting the hell out of something I am not as comfortable as in a loose sweater, you know?

But I feel comfortable IN it, it is just that I am more conscious about the belt around my waist, that the skirt may split open a little…

Whereas an outfit like this, I wear it, and forget about muffin tops and bending down to pick up something:

What qualities distinguish the most comfortable from the least comfortable pieces in your wardrobe, in terms of fit, material, or details?

Most comfortable

Properly fitted to my body — not awkwardly tight in the shoulders, or the armpits so I have range of movement (I hate being constricted), and is a long enough hemline for me not to feel awkward if I need to bend down for something.

I also love very luxurious fabrics – silk, cashmere (not the itchy cheap kind), soft merino wools (again, no Banana Republic here for me, they itch like mad), and anything that feels drape-y and good on my body.

Most uncomfortable

Anything that is not a natural fiber. I really really detest polyester and its feel if it is not LUXURIOUS.

If I can FEEL that it is acrylic, if I can SEE that it is pilling throughout the day or picking up fluff, it drives me insane.

I also find my most uncomfortable tops and bottoms are the ones where the waist is an eensy bit tight… this is because I put on a bit of weight lately (all that damn candy at the office that I have sworn off on now), and it doesn’t make me feel comfortable.

Looking at the pictures of your outfits, how well fitting are your clothes?

Fairly well-fitted. I am not under any illusion that anything needs to fit to a laser-cut T to my body, which is what I used to think when I was younger (*sobs at all the things she had to donate / sell as a result after having Little Bun*), and the only problem areas are ALWAYS my shoulders.


My shoulders, my arm holes, if it feels tight, I feel very uncomfortable. I need this shoulder part to be FITTED but not tight. I really hate being constricted in my arms.

How do you usually style your outfits? Do you often tuck in your tops or roll up your sleeves?

I always do something to it. I always half-tuck in my tops.

In tees, jeans and even blazers, I have started cuffing them. I can’t leave a sleeve alone.

I always, ALWAYS roll up long-sleeved tops unless they are not meant for that like this shirt:

I always push up my sleeves on my sweaters too, by habit:

What type of accessories do you wear most often?

Lately, long necklaces, delicate, barely-there necklaces, rings, cuffs, and a watch.

No earrings, my ears are not pierced.

I try to pick either a necklace or a ring but the watch is always there.

The only time I’d wear both a necklace and a ring is if they are both delicate. Otherwise, if the necklace is a statement, the rings are not on. If the ring is a statement, I don’t have a necklace on.

I love a good bracelet cuff too, and will do a whole armful of them to have more impact:


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 1, 2019

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In a nutshell…

Save. Spend. Splurge.
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