In Ask Sherry

Ask Sherry: What name I go by & my intimidating wardrobe

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

You can ask any question using the form here.

Did you used to go by the name Serena or is that another blog? Thanks!

Oh no, that was me! I was using a similar pseudonym on the other blogs because I don’t like revealing my name, but then it just got confusing (even to me) as I was replying, so I decided just go with my real name but not reveal my last name — Sherry.

I respond better now when called by my name. 😉

Have you found the way you dress ever to be intimidating to people around you?

Yes. I mean, not that it bothers me, necessarily, but I have noticed that people (A) take note, and (B) dress up / dress better when they are around me or about to meet me. They’ve even TOLD ME THAT!

I feel a bit bad because I don’t mean to make anyone change their ways, but I have no control over what people wear, and what they think, but suffice it to say — I do not judge anyone for dressing down or up. You do you, boo boo.

I find very casual dress and lowbrow non-designer threads to be extremely non-intimidating. I’m worried I’m going to put people off if I dress too fancy/richly! Thoughts?

Yes, casual and lowbrow designer wear is very non-intimidating but for me, BORING. I dress for myself. Yes, it is partly for other people, and it feels great when someone says: Your dress is gorgeous! … but it is mostly for me and my mood.

I very much enjoy dressing up and looking nice because I feel good, and when I feel good, my attitude improves and I am much nicer.

Just today, I didn’t want to wear sunscreen, so I wore a tank top, jeans and a baseball cap. I felt like crap, went out feeling like crap, and basically tried to hide my face from the world.

In contrast, when I take the time to put on a bit of makeup, dress nicely, and THEN go out, I’m smiley. I’m presentable to myself, to the world, and that makes a world of a difference in my attitude.

Like this outfit above? I felt like a queen in it, and it was incredible how my gait and attitude changed the minute I had the outfit on.

If you put people off if you dress too nicely, you kind of have to know your audience, I guess. I wouldn’t wear nice threads to a farm, you know?

Dress for the environment. Dress as nicely as you can, for you, and if people whisper about how you look too fancy, or rich, you won’t hear about it or know it.

More than likely, I suspect they won’t think that at all. You are hyper sensitive and more self-conscious than anything because you THINK people are staring at you and judging you, but they really aren’t.

If anything, they’ll just see a well-dressed, put together person and think – She looks great! I wish I knew what she was wearing. Where did she get that bag? I’m going to secretly take a photo of her outfit and recreate it later (<— this is all what goes through my head when I see someone dressed well.)

I actually did this (a secret fake photo of Little Bun) because I was so in love with this girl’s outfit, from her oversized, feathery eye-lash top, her high-waisted shorts, down to her velvet black mules.

I had another girl on a subway I was staring at who was just stunning with Doc Martens on (now I want a pair!) but I wasn’t able to snap a secret photo of her without being obvious.

I sort of remember what she wore, but it has faded now.. I just remember thinking: I WANT A PAIR OF DOC MARTENS NOW.

Long story short, WEAR WHAT YOU WANT that makes you feel good. Who knows? Maybe everyone else will feel relieved and feel free to dress up a little too.

Still have a burning question?

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

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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. GYM

    Ahh I remember the Serena days too! 🙂 Lovely outfits, I hope I can dress up again one day when I don’t have messy mom hair haha.

  2. Alice

    I think the intimidation aspect also comes from your personality too. If you’re dressed much better that others around you AND are aloof and withdrawn, and tend to give off an uncomfortable vibe… Yeah. Many of Sherry’s casual outfits are toned down enough to not be intimidating, although it depends on where you live I suppose.

    1. Sherry of Save. Spend. Splurge.

      That is very true — if you dress too far up, it does mean you have to warm up your personality a bit to show that you don’t think you’re better than anyone else.

      My outfits these days are casual-ish, but in the office, I do wear heels and dress up..


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Save. Spend. Splurge.
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