In Discussions, Style

What for you is the difference between dressing and dressing up?

They are one and the same for me, with a very slight difference to dress up from where I am coming from.

I dress up normally by most people’s standards, which is why everyone asks me why I am always so dressed up, but I don’t even think it’s something to remark upon the way others do, only because I think our culture in North America is to dress DOWN as a sign of power rather than up.

It’s a double standard, actually.

Wearing t-shirts, a hoodie with jeans and flip flops with messy hair means you’re a secret millionaire when you’re a man, but it makes you look lazy if you’re a woman.

This is what I normally wear and not just to work:

Still. I enjoy dressing up as my normal status quo, and I do it for myself.

I think it is a disservice to yourself and to others to not at least try to put some thought into what you wear, even if it’s wearing the same wrap dress over and over again rather than sliding into a slippery slope of yoga pants and stained t-shirts with a hoodie.

Now when I dress UP, I turn up the wattage big-time and people usually remark: “WOW” .. instead of “You clean up nice!” which is a bit of a backhanded compliment, meaning you are a bit of a slob most of the time.

Dressing up is when I think about the entire outfit from head to toe, including makeup.

I spend a lot of time on my makeup, more than usual (at least an hour), carefully concealing out my spots and achieving what I think looks like flawless, airbrushed skin.

The outfit when I dress up isn’t something I just pick out and build around on a whim of that day, it’s thought about in advance and planned out.

This is what I’d wear if I was dressed up; note how high the heels are!


The entire series can be found here: Women in Clothes Style & Fashion Survey

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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. Kristian Olson

    Such an interesting topic! I live in Wyoming (aka possibly the most casual place ever. People literally wear jeans to funerals). Like you, I get asked what I’m dressed up for a lot….. In general, I tend to think of casual as things I could wear when not at work- so, mostly jeans. Dressed up might be more professional, or, if it is for a social event, like you I tend to put more effort into make=up and hear high heels.

    1. Sherry of Save. Spend. Splurge.

      Jeans to funerals! O_o… I’d feel so strange.

  2. Elisa

    I used to dress well until my son born… ever since then, I’ve been dressing down and pretty much like a slob. Not losing the baby doesn’t help either. As I started to eat healthily and losing weight, I started to want to look like my old self. Hence why I just dug out my old clothes and displaying them in centre of my wardrobe shelves. It will be slow as I need to get back to pre baby weight but better than nothing right :)!

    1. Elisa

      Baby fat lol, not losing the baby 😂

  3. Tania

    I live in a casual place so there is little need to dress up. That said I’m not running around in athletic wear or hoodies half the time. I now dress the same nearly each day. I wear loose drapey clothing in natural fabrics with an interesting bag and modern handmade jewelry. That pretty much works for anything I have to do. Simple makeup and hair. I don’t worry about flawless skin at this point. I’m pushing 50 now and I’m embracing my signs of aging. The sun damage represents memories on the tennis court and at the beach with loved ones.


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