Top Fashion Questions Answered EP| 137

Do you have burning fashion questions? Have you been slipping into Holly’s social DMs to ask your deepest, darkest style questions? Well – you are not alone, because we get a TON of questions.  

So, we only thought it was fair to share one simple fact: Everyone has questions about ‘what to wear.” Every. Body.  

And Fun Fact: Holly LOVES to answer your fashion questions. So, if you have ever sent her a message then you already know this: HOLLY ANSWERS!  

It’s shocking. We know. But WE ARE THE BEST FASHION FRIEND YOU NEVER KNEW YOU NEEDED, remember? And we mean it. You are our Fashion Besties, and we are here to help.

This week, Holly does some shout-outs to listeners who have shared their own fashion concerns – which also just happen to be the type of questions many women “of a certain age” might have.


Question from Christine:

How to shop for clothes when vertically challenged (aka, short)?

Answers from Holly:

If you are 5′ 3″ tall or less, you are in the Petite category of sizing. This should not come as a surprise to you. You have always needed to make clothes work for you. So, no newsflash there.

The only rule you need to know is this: Buy only for fit. Not for fad. And certainly not on the wish that you were taller. Not. Happening.  

What IS happening is called alterations. Go to your local dry cleaner and make a new BFF with the tailor at your cleaners. Hemming a dress, skirt or pants is not rocket science! If your clothes fit you perfectly, it does not matter how tall you are. Or are not?

This may mean one extra step when purchasing something new to wear, but you can do it. And it is worth the minimal cost and time it takes.

From Lisa:

What are the rules for mixing prints, and can I really do it?  

Answers from Holly:

First, some key points. It takes a lot of confidence to pull off this look. It is advised that this style may be for seasoned and experienced shoppers! 

Next: but anyone can do it.  

Holly suggests concocting a highly curated mix for this look. Stay in the same color family, to start. If you are trying this look for the first time, do this: 

  1. Start with nice jeans as your foundation.

  2. Pick a nice jacket or blazer with a pattern.

  3. Layer a printed shirt in the same color family – and maybe with a smaller pattern – under the jacket.  

From afar, you will look well-dressed in a jacket and pants. But closer up, the ‘Wow Factor’ pops out from under the jacket.  


Do not try this look for the first time with flower-patterned pants and a polka-dot top. Most humans cannot pull this look off – and shouldn’t try. 

You CAN try a patterned bag or shoe, or other accessories with prints and patterns, as less risky alternatives.

From Sticky Bakery in Toronto:

What the heck does “dressing age-appropriate” actually mean?  (And yes, this question is from a bakery!! LOVE IT)

Answers from Holly:

While this topic is something Holly talks about EVERY SINGLE EPISODE, the term ‘age-appropriate’ can actually be confusing depending on how old you are and where you are in your life at any age.

As an example: Holly is 49 years old. But 49 for one person is not the same for another. If you are 49 years old with no children and are a fashion professional, your style needs may be different than someone else who is 49 and enjoying her days helping to take care of her new grandbaby.

Dressing age-appropriate simply means not giving up putting in some effort and wearing clothes that fit. Not dressing too old or dressing only to be comfortable. It also means not dressing too young. If your clothes are too tight, you are dressing too young. If your clothes are baggy, you are dressing for comfort. THESE ARE MAJOR FASHION CRIMES 

We don’t care how old you are, your clothes need to fit you well and you need to dress with intention. Meaning: Don’t give up. Don’t slob-out.

Holly encourages people to dress a little out of their comfort zone and be a little unpredictable. Do not dress “safe.” Take a small risk and get yourself in a place that makes people question your age.

Because that’s what great style is: When people have no idea how old you are

Suggested ways to combat dressing too old:

  1. Buy nice jeans that have stretch in them. Not high-waisted, Mom jeans. Not your old 501 Levi’s. Shop for jeans that fit well and hold you in.

  2. If you need new evening shoes and are worried your feet will hurt, take the extra time to shop for style and comfort. Not just comfort. No old lady shoes with padding and low heels, or no heels. You CAN find a beautiful shoe with a lower heel that is still dressy and fun.

  3. If you are ready to let your hair color go grey (which is fine), have a plan. Go to your hairstylist and learn how to transition your color. But more importantly, you must still have a hair STYLE. Just because you go grey does not mean that you don’t need a current haircut or you stop blowing out your hair. Long, wiry, non-styled hair is not OK.  You need to keep it looking sharp.

From Linda:

How can I dress better without breaking the bank when I work in a corporate job supporting higher-level executives?

Answers from Holly:

When you shop for brands that fit your body best, you won’t have to spend a lot to get a great look. Wearing the best-fitting slacks and dresses will automatically elevate your style. Then add fabulous accessories to pull it all together.

Understand what your body needs. If shapewear or support is needed underneath, get fitted for a great bra and wear the shapewear. 

Keep your shoes in great shape and buy yourself a freaking nice handbag. Shoes and bags do not need to be high-end designer brands, but they do need to look nice and be made of quality materials. Pick a color and style that is not trendy. And honestly, if your bag costs a little bit more, consider it as an investment in your career. You can easily use a nice bag for 10 years 

And the secret sauce? Gift yourself with a Jiffy steamer. Crisply ironed clothes go a long way in making your style look elevated.

From Maryann at Cape Wishes:

What is your favorite bra brand for someone over 50, and I mean, wayyyy over 50 

Answers from Holly:

Holly has 3 go-to’s for bras:


Prima Donna 

Rigby & Peller

A great-fitting bra changes your perspective on how you look in clothing. Just because you’re a Size A does not mean you opt out of getting fitted for a bra. Period. Exclamation point! 

If you are extra large, you need to get a minimizer or something that really fits. This means a bra that holds your breast tissue up and on the inside frame of your body – not down, not out, not up to your chin – to define your waist. Y’all know we’ve talked about this before. Go. Get. Fitted. For. A. Damn. Bra. 

Anyway, that’s it for this week. I cannot thank my new Fashion Besties Lisa, Christine, Linda, Sticky Bakery Toronto, and Maryann for writing in!

Do you have fashion questions for Holly? Go to her Instagram and leave her a DM, and don’t be shocked when she answers you.  

If she does not, by chance, see your message the first time, you have our permission to send the following message in all caps: I WILL NOT BE IGNORED, HOLLY! And then she will answer, we promise.  

Please subscribe, like, download, share, etc. the FASHION CRIMES PODCAST as much as you can! We just want to share the fashion love.

Listen now!

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