In Ask Sherry, Shop Quality Series, Shopping, Style

Ask Sherry: Do I ever feel self-conscious wearing luxury items?

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

You can ask any question using the form here.

Do you ever feel self-conscious about wearing luxury items? I think the answer is mostly “no” but I wonder if there are some situations where it’s a yes?

Well most of my luxury items — you cannot tell they are expensive unless YOU TOO are a connoisseur of fine things and can tell my sweater is cashmere or alpaca and not wool or polyester. In which case we are probably already friends and share tips on how to buy this stuff for cheaper.

I can spot these things on other people — just the leather of their shoes, the styling, the way it is designed.. I can tell whether it is cheap fake leather, low quality leather or high quality and therefore very pricey and beautiful.

I only feel strange if I am in areas or meeting people where I’d get negatively judged for it. I tend to not wear such items there but it is hard to not wear nice things as it is kind of all I own, and even my most casual items look pretty luxe (sweatshirts in cashmere, delicately made watches with hand-moulded bees…).

Otherwise no, I own it. I look good, feel good and if someone compliments me on it, I smile and thank them. I’m obviously not telling them where it is from or what it costs without them explicitly and directly asking me (rarely happens).

Does Little Bun wear “fancy” clothes? (My baby wears thrift shop clothes and whatever her grammas give her. I’m saving my money for when she’s a picky teen lol.)


He does not like it and it is a waste of money to buy such items for kids who won’t wear it and don’t care. He only wants comfy pants to easily pull down to go to the bathroom in, and cool shirts with neat pictures, sayings or flaps. He could care less about collared shirts and cool jeans at this point. I’m aware that I look very stylish in comparison to my little hobo child who is in a plain shirt and pants when we go out, but he is happy.

I have tried hard to get him to wear nicer collared polo shirts and so on but this baby of mine is very willful like his mother and does not want to be uncomfortable.

I’m saving the money for stuff he does want — stickers for instance and when he is older and if he cares, I’d be pleased to buy him beautiful coats, shoes and items for him to enjoy and not grow out of.

Now as a kid? Forget it. Hand me downs are where it is at.

What is the most casual outfit you wear these days?

Jeans, flats, tee. That is as basic as it gets to go out. I simply cannot dress down more than that.

Actually, this is the most casual outfit I have worn to date. I wore it, and felt so casual, I put on 4″ wedge heels and felt better.

Yep. Even casual stuff needs some bling.

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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In a nutshell…

Save. Spend. Splurge.
[ wealth. style. minimalism. ]


MOST DEBT: cleared $60K in 18 months

MONEY: Hit $1M personal net worth At 36

NEW GOAL: $1M in invested assets


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