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Ask Sherry: Orthopedic shoes, Styling Advice, Boarding Glasses and Career advice

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

You can ask any question using the form here.

hi! I saw your post about the Boarding Glasses.

After some time, are you still using them? Did they work?

So far, so good. Little Bun wears them and they seem to help. The only thing is if your child is INSISTENT that they wiggle their heads back and forth and refuse to take precautions to not exacerbate the situation in a moving car, you will still get nauseous and carsick. I think these may work best on things like trains. I keep Gravol on standby just in case.

What is your opinion on having a separate cell phone for blogging anonymously?

I would love to start an anonymous blog, but I want to buy a separate cell phone for my blogging and social media (to promote this blog).

However the type of cell phone I am thinking of buying would be a cheaper cell phone under $100, like from Straight Talk Wireless, they seem to have cheap cell phones you can buy outright and their monthly plan after that seems affordable.

I just like the idea of keeping everything separate from my real life and not having my contacts sync accidentally, you have to be super-conscious of each setting on each app to not have contacts sync.

Would love to know your opinion either way and what would you do if you were starting out today with an anonymous blog?

Sure that actually makes a lot of sense and would be THE MOST secure option out of all. You would not be making a mistake in doing so.

Hello there, this is____ and I received questions on IG which seem to be phrased in an unusual way for you.

So, in the spirit of paranoia, maybe please change your password? ๐Ÿคฃ


Thanks for telling me. It is likely not me, and they may have spoofed my account to message you. At any rate, to log into my Instagram I have set up quite a lot of long passwords and 2FA authentication, so it likely did not come from my actual account but another one. Or maybe my brain was not working and I typed the question oddly.

As a reminder:

I would never send links or ask you for anything that you did not ask for.

For work as a 55-year-old woman, should I:
A. Follow my podiatrist’s direction to only wear supportive, lace up or otherwise orthopedic-ish shoes; OR
B. Cram my wide, plantar faciitis-prone feet into some kind of low heeled pump or bootie for the “aesthetic value”?

(NO mules, NO loafers, NO ballet flats, NO Rothy’s, please).

I won’t purchase clothes or shoes until I get this resolved, it’s been years and I look terrible daily. I show up in faded black Levis, beat-up fabric New Balances, my husband’s discarded black t-shirts and cardigans. Not outfits, just coverings so I’m not, you know, naked. Just old, ragged, gray and black clothes. And a dearth of accessories.

I don’t feel I can address the style/clothing issue until I decide what to do with my feet. I want a personal style uniform or outfit formula, but that’s going to be very different if I’m opting to wear the “Anodyne #51 casual dress” or lace-up “Clarks Appley Tie” shoes I have my eye on than it would be if I give say some Sole Bliss low block heels a whirl.

And no, I don’t want to “vary it up” with both approaches: I want to pick a way and go with it. I like minimalism and would find value in a consistently put together look — whichever shoe that stems from. I want to reach into a closet of interchangeable items, and that includes the same style of shoe every day.

My workplace is business casual, but with BOTH jeans and “conservative walking or athletic shoes” allowed. I’m in corporate comms for a manufacturing company in Oklahoma, and my office is above the production floor. I work with mostly men, and they wear jeans/sneakers/golf or rugby shirts.

But as I’ve now fully disappeared into the faux paneling due to my descent into post-menopause, I wonder: Does it even matter what I wear? I know improving my style would help me feel less despondent about myself, but MUST that include a small heel, or can I wear what’s comfortable and doctor recommended? I can still be put together in a quality leather walking shoe. Men do it.

I’ve been wrestling with this for at least 5 years now. I have the means to buy myself a nice wardrobe, but I can’t because I can’t figure out what to buy. Every weekend, every evening, I read blogs or watch videos about personal style and business casual. I’ve had my flippin’ colors done multiple times — they say “Autumn” and I say “but my skin’s pink and doesn’t tan.” So, confused there, too. Also, I have bodybuilding trophies and was super fit my whole life, but now post-menopause, I don’t move at all and am sporting belly flubber.

Thoughts, commentary, analysis?

Put Yourself in My Shoes

Orthopedic shoes can be still stylish.

I would go with what is best for your foot health ALWAYS, first and foremost.

I would not want to end up older, hobbling having to undergo surgery and being unable to walk just for fashion. YOU DO NOT NEED TO WEAR HEELS TO BE FASHIONABLE.

I know you said no to loafers and ballet flats (my favourites), but have you said no to ALL the styles of loafers?

You have styles that are very fuddy duddy with those terrible tassels in front, but you also have very chic styles that are a little more pointed or a rounded toe, or the ever classic Gucci Jordaan loafer, worn by pretty much ever stylish person I see on Instagram (it makes me want a pair, myself), you simply cannot go wrong with such a classic shoe if you are into that whole vibe of menswear and classic pieces.

If all the young ones are wearing it, it cannot be a bad shoe! ๐Ÿ™‚ And it looks quite comfortable, frankly. That shoe could go with anything.

As for shoes itself – have you looked into the brand Taryn Rose? They are made by an orthopedic surgeon and look quite stylish.ย I have to say, a lot of them look quite good, and seem to be the best brand for comfortable shoes with a bit of a heel.

UPDATE (2022 Oct 20th): A reader who suffers from this issue sent me two more brand names for great support:


I do agree that shoes make an outfit, but I would say that the outfit comes first before the shoes. Do not let these shoes hold you back! Flat shoes are comfortable and smart-looking, even orthopedic ones, and I would 100% focus on wearing clothes that fit and are comfortable while being stylish.

I think your real issue is you do not know what to wear and are looking for people to tell you what to wear. Have you thought about trying a wardrobe consultant?

You know who I really like, her name is Alyssa Beltempo. You can ask her to help you review what is in your closet, try things on, and offer advice on what might look nice.

Here is her Youtube channel but she also offers private consultations which I think would be wonderful for you. She is very kind, knowledgeable and all about sustainable fashion.

For a very quick overview (without knowing you, seeing you, or having gone through your closet), for colour picking, my best advice is to pick colours you love.

You will NATURALLY like colours that look good on you. I know it sounds insane, but I do not like muddy tones like chartreuse, browns, anything with too much yellow in there, and they are EXACTLY the kind of colours I do not enjoy wearing.

In contrast, I really like jewel tones, vibrant colours, clear blue-toned pastels.. and those look the best on me.

You could also just simply go and try on various colours in things, and see how you feel in them, if it is not an immediate YES then it is a no.

As for body shape – everyone has issues. No body is perfect and if they are, they are spending a lot of time not eating, working out, and trying to maintain it which is something I think we should all shelve under “unattainable lifestyle” and love the body that we do have, rolls and all.

For belly flubber (which I also have), I find what works is thicker fabrics, nothing that clings, and using belts to create a waistline. I also like dresses for this reason and skirts, as they flow over your body.

Shopping, and style in general is not something that is effortless and happens overnight no matter what articles or videos tell you. It takes YEARS of shopping, making mistakes, and experience to get to where you might get a sense of your style.

A book I could recommend to jump start all of this is this one:

Her workbook / exercise book where you log all of your looks and how you feel, are excellent exercises to go through. Long story short, I would suggest going on Pinterest and start looking around at what you like to wear.

Do not worry if it will flatter or fit your body, just check out what you LIKE. Once you gather a board of pins for inspiration and style, you could then see patterns in there – is there a lot of a certain colour? Neckline? Skirt or dress length? Do you like a lot of accessories? Minimal?

Maybe it is also just a question of keeping what you love to wear (let’s say it’s wide-legged comfortable pants), but making the length ankle-length rather than longer.

Style rules are not as applicable as they once were in the past, so rigid and dictatorial to tell you what you could and could not wear (oh those vintage magazines were so bossy!)… and these days, it’s quite fluid as long as you feel good in it.

Remember that style also evolves. I would not wear what I wore when I was a teenager today, but I could wear a hint or an inspiration of what I used to wear, just perhaps in better fabrics (secondhand!!!), and with less of the look and more of a subtle twist on it.

I have also in recent years gone towards looser fitting clothing, flatter shoes, and baggier fits, when in the past, everything was very fitted. Your tastes should and can change.

(Email me! I would like to see how else I can help. You can contact me here.)

Do you still offer career coaching and consultation?

I saw that you had disabled the booking links. Will you be offering it again in the near future? Thank you!ย 

I still do it but only on certain days/times, around my work calls and schedule. Just email me please! ๐Ÿ™‚ You can contact me here. It also depends on what it is you want coaching on as well. There are some areas I will not touch as I am not the one who can answer these questions, but I can help redirect you to others! ๐Ÿ™‚

Still have a burning question?

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

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