fashion over 50 shopping trip

Taking My Mom Shopping & Finding Clothes That Flatter

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This isn’t the first time my mom has been on this blog, but it’s the first time I’ve documented one of our shopping trips! We’ve been tentatively planning on something like this for a while now, and we were finally able to make it happen, masks and all.

My mom went through the steps in my eBook on building a wardrobe from scratch and finished reading it with clarity on her body type and personal style. Using the tv example from the eBook, she found that her idea of the perfect outfit uniform is pants (or jeans) with a nice blouse. Perhaps a cardigan and a nice bag and that’s it for the most part! Simple yet still nice. An elevated twist on your day to day look.

My mom is not at her goal weight, but she still wants to look good in the in-between. Bravo! And…don’t we all? Though my strengths are more in outfit ideas and styling (not dressing specific body types), I was determined to help find some clothes that flatter.

After finding her personal style and cleaning out her wardrobe, she found that she was missing nice tops! So together we set out to find some clothes that flatter her upper half and thankfully, we found a lot. Don’t you love shopping trips when that happens? Here’s the 411 on our shopping trip & our finds!

Finding Clothes That Flatter

In addition to shopping, I also shared simple tweaks on how you can elevate your look. If you notice in the below shopping photo, she layered her husband’s thermal top under her blouse. I let her know that it could be better. 🙂 Since the reasoning was that she’s always just so cold, I advised that she focus on layering over her tops instead. So instead of a thermal type long sleeve poking out underneath, switch it out for a tank top for neck coverage or something that doesn’t hang past the blouse. Then put a nice, thick cardigan over the blouse. Still warm but more elevated!

Now back to the shopping part. My mom was looking for nice tops the most as that’s what she found her closet was lacking. We wanted to minimize the stomach area, without being so loose and shapeless that it looked like she was wearing a tent. You’ve got to emphasize the good things!

I found some key things that worked for her goals and once I was able to pinpoint what looked best on her, it was a matter of finding those same details in just different styles. If you have a similar body type, this is what I was looking for:

  • Slight v neck
  • Nothing clingy around the midsection
  • Tops with detail around the neck to draw the eye up
  • Looser/flowier tops with a softer/sheenier material (think blouses & no plain t-shirts)
  • Color blocking- with a dark color around the midsection
  • Tops with shape/detail around the neck and/or arms, while keeping it loose elsewhere
  • Small scale prints
  • Wrap top
  • Tie detailing around the waist

Tip: You’ve got to go into a store and try stuff on! Bring a friend, sister, or daughter for some encouragement and honest feedback. It’s easy to get stuck in a rut. Go to stores you wouldn’t normally go to and don’t even worry about the price. The point of this is to see what styles are flattering on you.

Once you know what looks good on you and what you feel comfortable in, then not only will you feel more confident, but you’ll be able to shop online easier too.

Currently, with covid, you may have to bring clothes home to try on first, but don’t let that stop you. You can always return what doesn’t work. And if you’re afraid you’ll never do it- set a time in your phone to do it that same day.

As I said earlier, the shopping trip was a success! My mom found a coat, boots, pants, and tops, but I’m going to highlight the 5 tops she got in this post as that is what we were looking for the most. Also, we mainly shopped at TjMaxx so unfortunately, you can’t buy the exact item, but I’ll highlight similar things in the shopping widget instead!

Top #1

I love this classic black & white top! It has interest and style with the faux button-down underneath. The polka dots are cute and whimsical, without being childish. Black is always a slimming color, but the white is a nice contrast and keeps it from looking too dark, as all black is more my thing and not my mom’s. 😉

In this look, she’s pairing the top with drawstring dress pants (classy yet still comfortable), but you could easily pair it with jeans too. This top could go from professional to put together yet casual really easily!

Top #2

This top is great because it’s not too tight around the middle, but the gathered sleeve detailing makes it interesting, cute, and adds some shape! Plus, it’s long sleeve, so great for those that get cold easily and/or don’t like to show their arms.

Top #3

The photos below are for try-on purposes so she’s missing an undershirt, but this shirt was a great find too! It hit a lot of the things on the list. V neck, neck/chest detailing, cuffed at the wrists/arms, loose material, and a cute print.

Top #4

Similar to the first top, this classic black & white beauty is dark in all the right places while still having great contrast. The visual length helps to elongate the body too!

Don’t forget that the right pants matter. Not just style but fit as well. It’s really important to have a good foundation.

Top #5

A little bit of color never hurts! This v neck shows some skin so the top doesn’t look stuffy, but yet not too much skin that it would make my mom uncomfortable. Generally, smaller scale prints are more flattering than larger prints if you’re looking for something to slim out your body!

Related: Wondering What Colors Make You Look Skinny? Read This Post!

Finding clothes that flatter and having a wardrobe you like can seem like an impossible task at times. But your confidence depends on it!

Want to give this whole classic wardrobe thing a try but don’t know where to start? Check out my eBook on building a wardrobe from scratch. Step by step we can get you from feeling frustrated with your wardrobe to confident and happy!

If you liked this post then you’re going to love all the ones below!

How to Have Style in Your 40’s, 50’s, & Beyond
How to Dress Like a French Woman Over 50
Fashion for Over Fifty | What My Mom Has to Say About Fashion

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shopping with my 58 year old mom
finding clothes that flatter


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.