Once again, this post is part of a styling adventure, based around my reader (and now new friend!) Carrie. She is from the US and she has been selected to be one of the 300 lucky people flying to Australia with Oprah Winfrey in December.
Last week I threw together a kind of “fashion inspiration style board” to gel some ideas I had for Carrie.
This week, I’ve thrown some more outfit and wardrobe ideas at her, and she has come back to me with some responses.
It’s been such a fascinating experience for me to style someone else, and our conversation has highlighted so many issues in choosing a wardrobe, especially if you play many roles in your life.
I have since gotten to know Carrie – what she does for a living, what she does all day, where she goes when she gets dressed up, what she usually wears when she dresses up.
It turns out that Carrie has a blog! And she has offered up her side of the experience, by allowing me to publish a link to her blog – Bite Sized By Carrie.
So here are some of the major points that we have come up with so far.
Start With the Big Themes in Your Life
Most people have a theme in their life that influences the way they dress. You’ve probably heard of these styles that are often talked about: A simple and classic style, a free-spirited bohemian style, a romantic feminine and pretty style, an urban edgy-cool style, a vintage and eclectic style, a beachy and sporty style, etc.
My own secret is that, since my teens, I have been very drawn to the “rebellious” look. I have experimented with everything from gangster, goth, punk, rock and roll, heavy metal, and grunge… but now haha, it’s evolved to just elements of the “tough, rock-chick look”.
And although I don’t actually dress all-out like this, my twist on modern classics is usually with a slight, dark twist, however subtle. Interestingly, I have not in any way, ever, been drawn to the pretty-pink-princess look!
Anyway, Carrie is a mother, which is a huge theme in a woman’s life!
Generally, when women are in “mother-mode” they are practical and always on the go. For example, very rarely do you see a mother in a two-piece white suit with lace-trim attending their child’s school assembly day. Like me, Carrie spends most of her days in jeans and a t-shirt. But, when a woman comes out of mother-mode, what is their “default” style?
Also one of Carrie’s biggest passions in life is food. She runs a catering business and she just loves cooking at home, and with the kids. I found it lovely to know that she loves “food colours” such as mushrooms, deep reds, plums, burnt oranges, browns and caramels. Yum!
So it’s quite handy to start by finding a style that you are mostly drawn to, and which suits your personality.
Dress to Match Your Life (and Partner!)
Carrie mentioned that when she goes out with her husband, she prefers to dress to his style, comfortable and very casual, so that she doesn’t look like an “exotic date”. He’s already been playing dress-ups all week at work, so weekends are for relaxing and being super casual.
As Carrie and I are both ethnically Asian, I can totally relate!
In my experience, even though Asians aren’t that rare in Australia, there is this lingering racial stereotype that a slightly older white guy must be “paying by the hour” for the company of a younger Asian woman. This impression is only exaggerated if the Asian woman is overdressed compared to the guy. My husband and I have had to show people our wedding rings to convince them we are married!
So, when I go out with my husband, I like to make sure that we match in our level of style. If he’s wearing a t-shirt and jeans, you can be sure that I’m NOT wearing knee high boots, a mini skirt and a low cut top! Ha!
But since I like to dress up at any excuse, I have somewhat solved this problem by upgrading my husband’s wardrobe. I mean, I love him the way he is, and I love him even more in a slightly more stylish shirt, and maybe some “pointy” shoes (as he calls them).
It used to be that I would just lay out what I expected him to wear on the bed, but now he is so well trained that he knows not to choose a shirt and pants that both have stripes! I’m so proud!
So work out what are the events, places, occasions that you go to – Out to dinner with your partner/friends, out to watch a play, home dinner parties with friends, the occasional wedding? Does you workplace allow, or require, you to dress up?
Dress to Suit your Budget!
Carrie says in her blog: “We both have the same goal: Choosing clothes that I would actually buy, clothes that I would actually wear.”
I completely agree. This has been the biggest and trickiest goal for this styling project.
Understandably, Carrie is a little hesitant to spend hundreds of dollars on clothes that she might not have an occasion to wear, and only end up wearing once.
And I love it when people say this! I mean, who wants to flush money away pointlessly? It’s the kind of thing REAL WOMEN actually say about fashion, and something that glossy fashion magazines NEVER SAY.
The key to dressing a bit more stylishly, is buying dresses and tops are a bit pricier, higher quality, longer lasting, and more importantly, VERSATILE – so they can be worn for both day time and night time, in different mix and matches.
Learn How to Mix and Match
I whipped up a very simple examples of how to mix and match pieces with some “essential pieces” to create a “smart look” – meaning a slightly professional look.

It helped immensely to find that H&M had already styled the exact kind of “look” that I had in mind for Carrie, onto a real human being (although this human being is that rare sub-species – “the hot model”). Laid-flat clothes just don’t do any justice to an outfit.

All the pieces can be worn dressed up or dressed down.

Carrie also told me that she loves that I’ve chosen clothes from shops that she is comfortable with. I did that deliberately, since it is really important to go shopping for a new wardrobe with confidence as to sizing, quality, etc.

Her response was: She loves ALL the styles and colours! She loves that she loves it! She’s really liking the look of skinny pants and the suit jackets. And she says she’s learning an incredible amount about fashion and styling.
As am I!
I was so relieved that she liked my “style boards”. Haha, I was really nervous about her response.
And these are her kind words about my choice of shoes (shown last week) for her.

“Holy Crap! I could eat those shoes on the left. Those are terrific! I checked out the site and those you picked out for the style board are EXACTLY what I would have chosen… from the whole site. Are you sure this is the first time you’ve styled someone else? You know what works!!”
Yay! As you can probably tell, Carrie is not shy about telling me what she thinks.
She also mentioned that she popped into H&M, after seeing my ideas, and tried on the skinny pants that I suggested – but “apparently you need legs that don’t exist!!”. They didn’t fit her and so she’s going to try look for some in a few other shops.
Buying The Clothes
So Carrie has been actively out and about buying a few bits and pieces, based on my ideas.
Of course she’s running into fitting problems, size problems, style considerations once she’s actually wearing the clothes, and value versus costs considerations. Not to mention that she’s limited by the styles and sizes she can find in the shops. And that’s shopping for you!
So I don’t expect her to buy everything I’ve suggested.
I’ve also organized some of my favourite online shops to help Carrie experiment and build her wardrobe by supplying some garments and shoes (for free!).
These suppliers are all over the world – America, Britain, and Australia, and I adore these outlets because, even after wearing their stuff a LOT, I still find their stuff to be excellent value. So I am very happy to recommend them.
They are, in alphabetical order, Abi and Joseph,
Asos.com, Betts Shoes, Birdsnest and Fashion Junkee.
Hopefully, next week, I’ll have some photos of all the clothes I’ve arranged to have sent to Carrie. Maybe even Carrie wearing some of them?
How exciting. Carrie playing dress-ups!