Age-Appropriate Dressing: How To Style at 18 vs. 50

Age-Appropriate Dressing

How This Post Came to Be

This is not what I originally intended to write about this week… But often these become my best blog posts. What’s the saying man plans and Gd laughs?

Let me give you a brief rundown of what my monthly blog and Instagram photo sessions look like. I collect from both local and online retailers and brands items that catch my eye.

The goal I have in mind is twofold:

  1. What have my clients been asking about (ie certain trends or life events they have coming up, like a graduation or Passover/Easter)

  2. What would help update their existing pieces (and therefore my own) to make their outfits feel up to date and current?

And each month I have a rolling rack that houses the clothes until photo day. Normally, this rack sits there without a second glance from anyone in my family. But this month, Maggie, my 18-year-old daughter, began admiring my selections and commenting “this is cool, I’d totally wear that”... To which I responded, “cool, how would you style it?”

And so this post was born.

Age-Appropriate Style

What Is Ageless Style?

I’m often asked about age-appropriate dressing, and I honestly abide by the rule that if you love it and it makes you feel great, you should wear it. But the truth is, many women have turned off the inner voice that tells them if they love it or not. And that then makes it challenging to know if they feel great and if they should then wear said outfit.

The other curveball is that when you have teen/young adult daughters, they more often than not, DO NOT WANT THEIR MOMS TO DRESS LIKE THEM. And while that may not be fair - especially to those 50-year-olds that work their butts off to have the body of a 20-year-old, I can honestly understand where the daughters are coming from. 

Just for the record, I am 1000% not one of those women that can wear what I did when I was 20. I’m not mad about it, in fact, I’m proud of the journey my body has taken. And, I am also equally as glad I have the armor of clothes and the optical illusions they create to help me feel confident with all the changes that have taken place.

The past 3 decades have left their mark on my bod. Gravity, pregnancy, childbirth, surgeries (multiple major hernia surgeries), and to top it off, menopause, my current nemesis. It all makes me tip my hat even more to those that have successfully stood the test of time. Yes, I’m looking at you, Jennifer Lopez!

Age-Appropriate Style

True Story

About 10 years ago, way before Maggie and I were at this crossroad of even having the possibility of wearing the same clothes, one of the high school girls at her dance studio confided in me about this issue. This young woman was blessed with magnificent genes and a mother that was able to rock a string bikini flawlessly. In fact, the mom and daughter were able to share the same bathing suits, often swapping tops and bottoms to make mix and match sets. And while the daughter was proud of her mom and her ageless looks, she was also super uncomfortable with her mom dressing like a teenager (her words, not mine). The daughter knew her mom was loving and stable and frankly not promiscuous at all, but what she was wearing made people think otherwise, and the daughter was beside herself. 

I wish I could say I had brilliant words of wisdom I shared. But I didn’t. I really just listened and sympathized. However, the interaction did give me a really big ah-ha moment. 

How We Each Styled the Same Pieces

So Maggie and I each took some items off the rack and styled them our own way, for our own style and taste  - and incidentally, we each approved of the other's interpretation. This may not seem important, but what I learned from the story above is that it is important to have the blessing of those you love - and it is also a two-way street. If I am going to expect my daughter to dress in an appropriate way (on specific occasions) then I also care about how she feels about what I am wearing.

The Suit

The Suit

This suit is amazeballs. It’s soft, and drapey (in a good way). Slightly unstructured so it feels finished but not uptight. And for those color adverse, it also comes in black. And from a functional wardrobe perspective  - a suit is ideal to have because it really gives you 3 outfits in one. You can wear it as the whole suit, and then you can break it apart to wear with other items so it offers optimal versatility.

How Hallie Styled It:

I wore it with heels and a tighter tee-shirt to give it a more feminine vibe, and then also swapped the blazer for a cardigan for a business casual feel. I paired it with a belt in a similar color so it highlighted the smallest part of my waist.

How Maggie Styled It:

I didn’t want to look like I was going to an office so a cropped tee-shirt and chunky loafers made it feel fun for me. I also didn’t wear a belt so the pants became more of a low rise.

Shop The Looks:


The Lace Top

This top gains its appeal because it’s more than a black top. The lacy, crochet detail is what makes it pop. The challenge however is that it is completely see-through. Probably good for Maggie and not as good for me, lol!

How Hallie Styled It:

For me I was not going to go bare midriff (note the multiple hernia surgeries discussed above - my midsection is a treasure map of scars). However I do like the idea of seeing something tighter under a boxier top like that. I also wanted to stick to a column of color so I looked taller and so the cool lace top could be the hero of the outfit.

I picked a white cami as opposed to black because that helps keep the lines clean. For more info on what color cami to wear under what top - check out this post

How Maggie Styled It:

I wanted to show a little skin but not too much. So I put this with a cropped tank. I’d feel comfortable going out to dinner with my grandparents in this and that’s sometimes my test. I also wore my mom’s old low-rise jeans and the boots I borrow of hers without permission when she goes out of town - shhhh!

Shop The Looks:


The Wide Leg Jean

This jean style is the new kid on the block. It’s a high rise with a full wide leg that hits the floor. The fitted waist balances the long and full bottom to give a nice silhouette. It’s probably not an everyday jean. It’s more of a “dressy” jean, trouser style. And it’s nice to add a different shape to my denim collection.

How Hallie Styled It:

I love how these are ecru instead of white, so they feel more wearable year round. Even though white CAN be worn year round. Because ideally you want this pant to hit ¼ inch off the floor, it requires shoe commitment - meaning, you need to decide what height heel you’re going to wear them with and stick to it. I’m a blazer girl at heart so pairing these with a blazer and tee-shirt felt very comfortable.

How Maggie Styled It:

I loved the color of this top - it matches the orchids my mom keeps around our house. And putting it with a heavy black belt and my chunky loafers (my 18th bday present) helped this feel like a young person outfit. I’d probably also wear it with the cropped tee-shirt from the suit outfit and a leather blazer.

Shop The Looks:


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