How to Wear it at Any Age – Volume 3

Last updated on January 9th, 2023 at 12:31 pm

And we’re back with How to Wear it at Any Age – Volume 3. If you’re new here, here’s how it works:

We both decide on three items that we want to style. We do not share how we were going to style each one, so that we can’t influence each other. You’ll see from the results below that in some ways we are alike and some ways we are different. But we hope in all cases we give you some style inspiration, no matter what your age or life stage! 

The Challenge for How to Wear it at Any Age – Volume 3

How to Wear It At Any Age - Volume 3

For Volume 3 we selected, from left to right, Pink linen blazer from Old Navy, Red lipstick from Maybelline and a casual tank maxi dress from amazon.com.

**This post contains affiliate links and we will be compensated if you make a purchase after clicking on our links. Also, as an Amazon Associate, we earn from qualifying purchases.

Let’s start with what could be the most challenging for How to Wear it at Any Age- Volume 3 first: finding the perfect red lipstick.

Red lipstick 

Jen’s Lipstick Selection

Anyone can wear red lipstick, no matter their age or skin tone! It’s just a matter of finding the right color for you!

Remember when we talked about finding your undertone? Figuring out if your skin is cool, warm or neutral is the best place to start for finding the best red lipstick. 

For a more subtle look, pick a red lipstick that has a similar undertone to your skin. Or for a bolder look, pick a color that’s opposite from your skin tone. 

Maybelline Red for Me - How to Wear it at any age

Cooler colors are blue-based and include cherry, watermelon. Warm colors are more orange-based, and include colors like salmon and terracotta. 

Cooler colors also do a good job making your teeth look whiter! 

I’ll also change up the type of red lipstick based on the season. During the fall I’ll go for warmer reds, and spring/summer I’ll wear cooler colors! During the winter, I’ll change it up between warm and cool colors. 

The lipstick I’m wearing here is Maybelline Red for Me, a gorgeous color and great formula. And affordable too! 

Maybelline Red for ME

When I wear red lipstick, I usually keep the rest of my makeup pretty simple. Minimal bronzer and blush. Neutral brown eyeshadow, and black winged liner. And lots of mascara! 

When applying any bright color lipstick, make sure you use a lip liner to keep your lipstick from feathering. 

If you don’t have a matching lip liner, that’s ok! Use a lip liner that is close to the color of your lips. Start by outlining your lips, and then fill your lips in. This will help your lipstick stick better!

After putting on your lipstick, you can go back in with your lip liner if you need to define the lines more. 

If you have any lipstick that’s gone out of your lip line, grab your concealer and a small brush and clean up those edges! 

Dianne’s Lipstick Selection

I agree with everything that Jen stated above, especially about matching your skin tone. On an everyday basis, I use cool tones for my make-up. But I will go “rogue”, especially in the fall and wear more warm colors in my makeup palette such as browns and rusts. But, since it’s summer, I went with more of a cherry red. It’s a cool tone and it’s nice and bright for the season. I chose Maybelline More Ruby.

Dianne - How to Wear It At Any Age
Maybelline More Ruby

I know that when we get to a “certain age” we can start to avoid bright lipsticks because of those little lines that start to form about our lip lines and we don’t want to bring attention to them. That’s where the lip liner comes into play. As Jen aptly said, you need the lip liner to keep your lipstick from feathering out to those areas.

It bears repeating that you should line your lips and then fill them in. You don’t want to just line them, I know from experience. When I first starting using lip liner I only outlined my lips and then went to dinner. When I went to “powder my nose” after dinner I was mortified to see that my lipstick was gone, but I still have the lip liner on. Needless to say, that was not a good look (and I never forgot it!

Pink Linen Blazer from Old Navy – $35

Jen’s Styling

Jen - How to Wear it At Any Age

I bought this blazer at the very beginning of quarantine when I thought we’d be going back to work sooner rather than later. 

I know I don’t wear a lot of color, but this was my attempt at adding some to my wardrobe. 

This is something I would wear with jeans and a white shirt, or this would look so pretty with a floral dress! 

I wore this shirt on Easter this year with jeans, a white bodysuit, my Chanel dupe flats from Target and bunny ears! 

The color is so pretty, and the linen is light enough that this blazer works for the spring or summer! 

I also consider stripes a neutral, so a shirt with a lighter color stripe would look super cute! 

Dianne’s Styling

I love this linen blazer! It’s perfect for summer and it can be dressed up or dressed down. We decided to style this as a work piece because of that.  It really can go either way and look great.

Dianne Blazer - How to Wear it At Any Age

I chose to style this in a more traditional way with straight leg pants and classic pumps.  But I also didn’t want it to be “all business” so I added the floral top, also from Old Navy. Because this blazer is a really soft pink, I originally thought that I would have to go with a more neutral colored shirt but when I found this perfectly matched top, I knew it was the choice for me. I like to add feminine pieces to an “all business” outfit at times.

(Tip for shopping at Old Navy:  they tend to use unique color names for their clothes.  For example, this blazer is “shell pink”.  If you search “shell pink” on the site, you will usually find some coordinating items. Also make sure to scroll down on an item you are viewing.  They have a “Wear it With” section that can give you some great pairing ideas.)

Target Chain Link Necklace
Chain Link Necklace from, target.com, $14.99

For accessories, I added this chain link necklace from Target which is a great look for a business outfit.  It’s really a classic piece that you can use for almost any work outfit. It also comes in gold. I paired my necklace with some chain link drop earrings as well. By the way, you know it’s a classic and a best seller when I bought this necklace last fall and they are still selling it!

Jen and I have both talked about our Telfar bags before.  While they can be difficult to get (they open sales for each color on a specific day/time and they sell out in minutes), they are worth the wait.  They are another example of an item that can be dressed up or dressed down.  It looks great as a work bag, but you could just as easily carry it with jeans and a white t-shirt.  I am carrying the “Medium” shopping bag which is $202.  Their bags come in three sizes.

For my pants, I am obsessed with the Whitney High-Waisted Pull-On Slim Leg Ankle Pant from New York & Company.  These pants are so comfortable and because they are pull-on, you have a smooth look – no bumps from pockets and buttons.  They tend to run a little large – I am a classic medium, but I can wear a size small in these pants comfortably. They come in lots of colors and three different lengths too!

Tank Maxi Dress from Amazon – $29.50 (as of 6/23/21)

Jen’s Styling

This dress reminds me of one I wore all the time when I was pregnant, but this one is way more comfortable! 

It’s a jersey-type material, so just a heads up it might be a little clingy. I have a size medium here so it’s a little bit baggier.  

Jen - Maxi Dress - How to Wear it at Any Age

Depending on the occasion and the weather, I would wear this a couple different ways. 

Because it’s summer, I wouldn’t need a jacket, but this would look super cute loaded up with a couple necklaces and earrings, a cute bag, and my Target studded sandals. 

This look is more casual with the hat, but still sort of dressy with my studded sandals and Louis Vuitton bag!

If I was going into the office, I would pair this with a jean jacket and still be loaded up with jewelry! Depending on the season, I’d wear my studded sandals (our office was relatively casual-ish), or in the fall this would be really cute with a pair of ankle boots! 

And to turn this into a date night outfit, pair this dress with a faux-leather jacket and a fun shade of lipstick! 

Dianne’s Styling

Because I am only 5’3”, I tend to avoid maxi dresses, even though I love the look. But this dress was simple enough that I thought I could pull it off (you’ll have to let me know if I did!).  Because of its simplicity, you can really accessorize it in so many ways.  I chose the long scarf to give it an airy, summer feel, especially with the navy and white stripes. Again, because I am not very tall, I don’t wear long scarves very often.  But with the maxi length of the dress, I feel it looks in proportion.  

Dianne Maxi Dress - How to wear it at any age

I also love summer jewelry and wrote an entire post about it that you can read here.  I will pick out one specific pair of earrings from that post that I think would go perfectly with this dress and keep the summer feel.  They are a little pricey for summer earrings, but I think they are a classic that you can wear for years to come. 

I am wearing plain hoops in this picture to not distract from the scarf. I probably wouldn’t wear statement earrings and a scarf together, but that doesn’t mean you couldn’t. 

For the purse, I was torn between a red and a green, but ultimately I went with the green purse to add a pop of color, but still let the scarf be the star.  Navy/green combo is great for summer but I do love red and navy together also. I may have chosen the red bag if I was just wearing some plain jewelry and switched the accessory accent to the purse.

Kate Spade Bag - How to Wear it At Any Age

I bought this Kate Spade bag a couple of years ago, so it’s no longer available, but they do still have other bags in a similar color on katespade.com.

For the shoes, I was planning on wearing flats, but switched at the last minute to this small block heel thong sandal.  Remember me talking about being on the short side?  Well I thought that this small heel still looked casual enough and gave me a little more height. I do love Jen’s look with the studded sandals – I would definitely wear those too.These were also included in our “Best Casual Sandals for Summer” recent blog post.

So what did you think of “How to Wear It At Any Age – Volume 3”? Let us know your thoughts and also include if there’s anything you’d like to see us style! You can the entire series at our “How to Wear it at Any Age” section.