In Ask Sherry, Discussions, Style, Wardrobe Help, Women

Ask Sherry: How do you defined “well-dressed” versus “dressed up?”

You asked, and I am answering every Friday once I have enough questions!

https://docs.google.com/forms/d/1DKFg6SD0Kmb_0U5yb4OTNfkvfmsf5dWxJJbZTzUtH7M/edit

You can ask any question using the form here.

How would you define being ” well dressed “, as opposed to being ” dressed up “?

Dressed up is when you are in heels, a cocktail dress, hair did and makeup fly.

That for me is dressing up because it is wearing stuff you wouldn’t normally wear to let’s say go to the grocery store.

At least, I wouldn’t wear a cocktail dress or a ballgown out.. (OR WOULD I? LOL..)

Being “well dressed” doesn’t necessarily mean items without holes (hello super trendy ripped jeans and distressed items of all sorts), but it does mean taking care with how you look.

It could be something as simple as making sure your shoes are clean and polished, your hair not a mess (washed for instance), and your outfit is neat and it goes together for the most part.

That would cover “properly dressed” which is level one for me, but for the “well-dressed” aspect, it means that when I look at your outfit, I am thinking: She/He looks sharp. I like the way they did this, that they did that..

…and it doesn’t mean I would necessarily wear all of those items (or any at all), or that I love the look of jean vests with cropped high-waisted pants as a personal style on me, but I do appreciate the thought and effort that went into coordinating the look for the day no matter how artfully disheveled it may come off as.


Case in point: Today, I was taken aback by a stunning older women at least her in 60s, who wore this very chic vintage mod red dress with a lace white collar that had a cheeky embroidered “OUI” in red letters on the left.

She paired it with Roger Vivier-esque heels with the big bow in the front, her hair was tied back into a neat little chignon, she showed about half her thigh – it was almost a mini skirt, like a mod dress – and she had pearl studs in her ears, and very cool square, retro, hipster glasses from Prada. She. Looked. FLY. She looked amazing.

I was staring at all the details of her entire outfit because she just looked so impeccably cool and put together.

I felt like a slob in comparison (LOL) which is not easy because I was in a striped poplin cotton shirt, but had rainboots & a raincoat on which made me feel schlumpy (that is neither there nor here, however).

I would not in a thousand years put on that outfit of hers and feel comfortable in the slightest, but she wore is with such aplomb, confidence and chic-ness, I was applauding in my head.

I almost wanted to take a shot of her and blog about it but I wasn’t sure if she would feel weird.. or if I wanted to reveal that I was a blogger.

https://theurge.com.au/s/a-j-e/Aje-Natal-Top-Aje-6112182534182/35bceccc-91a6-43b8-8d56-880d07019e28

(See? I have rips in my distressed jeans but the whole outfit is still reading as “well-dressed”)

Anyway, well-dressed means that you took some care with your appearance today, in whatever way you wanted to, and you achieved what you set out to do – artfully disheveled, nonchalant and casual, or just impeccably chic and crisp.

You basically didn’t just grab some shirt off the back of your chair (we all know that’s where you keep your clothes, don’t lie to me, I KNOW), and some jeans out of the freshly washed laundry basket you have been procrastinating on to put away 3 weeks ago.

You did something with your face – sunscreen, brows, a good lipstick – or you did something with your hair and you feel great.

THAT, is well-dressed. It’s half intention & mental feeling, half execution.

Still have a burning question?

You can ask any question using the form here and all of my previous Ask Sherry posts are here.

Share Tweet Pin It +1

Sherry of Save. Spend. Splurge.

Millionaire at 36 after getting out of $60K of student debt in 18 months, a little over a decade earlier, using TheBudgetingTool.com. Since then, I have paid my $600K home in cash (my half was $300K), my $180K casr in cash, 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 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.

You may also like

Previous PostWeek of Money: Where I start prepping for a girls' weekend in NYC
Next PostIn the world of Save. Spend. Splurge.: This is why you'll always be poor

No Comments

Leave a Reply