Last updated on January 9th, 2023 at 12:33 pm

Welcome to “How to Wear it at Any Age” Volume 1. We are starting this brand new series that we think you’ll love. We both have loved fashion our entire lives and we’ve often had conversations about what’s “age appropriate” – for both of us! When you’re on the younger side (like Jen), you don’t want to dress like you’re still in your teens. And when you’re on the older side (like Dianne), you don’t want to dress like you THINK you’re still in your 30’s or younger. The truth is, we both believe you can wear whatever you want – how you style it is key. (Although neither of us is sure we can pull off a crop top at either of our ages!)

So this is how the “Wear it at Any Age” series is going to work. We both decide on three items that we want to style. Two of them are items we’re comfortable with and one is just a little outside of our usual comfort zone (hello, chain belt!). 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! (Please note: as an Amazon Associate we may earn for qualifying purchases.)

The Challenge

Here are the items that we chose to style:

“Chanel” Inspired Cardigan

Jen’s Styling – Chanel Inspired Cardigan

Chanel inspired cardigan is from local Detroit clothing company, Dallas and Dottie (no longer available, but they have other awesome stuff).

This cardigan is the epitome of classic. It looks like the much-loved Chanel tweed jacket, but at a much, much, much lower price point. Would I like to have a Chanel jacket? Sure. For thousands of dollars? Nope

This cardigan would be perfect for working in an office, where you don’t have to be dressed up every day, but you still want to look nice. 

I’d pair this with a basic top, to keep all the attention on the cardigan. And either jeans for black pants. At the current moment, the thought of trying on my work pants is a little cringe-worthy, so I went with a darker denim. 

Add in some gold jewelry, cute shoes, and we’re ready to go! 

I also paired this with my vintage Chanel bag. I got this beaut on Poshmark for a steal! The only downside is when holding it by the chain the shape gets messed up. Does anyone know how and where to get vintage designer bags fixed up? 

What else I’d wear with this:

Other Chanel Inspired cardigans
White House Black Market
Express
Mango

Tops
V-Neck Bodysuit 
The Drop Cutaway Racer Tank

Jeans/Pants
Dark Wash Skinny Jeans
Raw Hem Skinny Jeans (I won’t give up on skinny jeans!)
Twill Straight Ankle Pant

Shoes
Ema Block Heel Square-Toe Pumps
Vince Camuto Mules

Bag
The Drop Foldover Clutch
Belted Satchel Bag

Dianne’s Styling – The Chanel Inspired Cardigan

I fell in love with this sweater the minute I laid eyes on it. I love all things Chanel or “Chanel inspired” and had just purchased some faux leather leggings when I found this sweater. The sweater and the leggings seemed to be perfect match. When I wear my leather leggings I do like to add a feminine touch, which is why I added the pink pearls. The pearls are also very Chanel-like. I matched the pink pearls with a pink tote, again for that touch of femininity.

While this look is a little more fall or early spring, you can swap out the leggings for some ankle pants and swap out the boots for a strappy sandal. I would even pair with white jeans for late spring/early fall.

What else I’d wear with this:

Other Chanel Inspired Cardigans
Venus
Saks Off Fifth

Tops
Express
Amazon Sleeveless Pleated Top

Pants
Slim leg ankle pant
White jeans

Shoes
Black Sandals – Nine West

Accessories
Convertible Necklace – White House/Black Market
White Crossbody – DSW

Chain Belt – Dianne’s Styling

This chain belt is from New York & Company. This particular belt is sold out, but they do have others.

I’ll admit it – this look took me back to my days in the office before dressing became more casual. There are days that I miss that. What I love about this look is that you have three classic pieces – a white cotton blouse, a black pencil skirt and black pumps. The chain belt gives it just a little bit of flair. I also love adding red accents whenever I wear black and white – it’s just the pop of color that the outfit needs. My bag is from telfar.com (they can be somewhat hard to get – you have to be diligent

What else I’d wear with this:

Tops
White Cotton Blouse Bodysuit – Venus (I wish I’d had this for this outfit)

Dresses (I would definitely wear this with a dress)
Sheath Dress (for now) – White House/Black Market
Sweater Dress (for later) – Amazon

Accessories
Oversized Croc Clutch – Amazon
Amazon’s The Drop Cross Handle Tote

Jen’s Styling – Chain Belt

Not going to lie, I had no idea what to do with this. I Googled, I looked all over pinterest, and my initial thought was “I’m not cool enough for this”. 

But I did end up putting together an outfit that I like and would wear! I would wear this out on a date night with Mike, when we’re comfortable going back out for dinner and drinks someday. Hot mom coming through! 

This top is a bodysuit from Abercrombie. This exact one isn’t available anymore, but something similar here. 

When I was in highschool, Abercrombie was all the rage, but forgot about it once I got to college. When did Abercrombie start having such cute clothes that aren’t just for teens? 

I’d also pair this with jeans, since Mike and I don’t typically go anywhere super fancy. 

This belt adds a cute, dressed up touch to the outfit. 

Plus the gold chain belt coordinates nicely with my Gucci Marmont bag – also from Poshmark! 

Who’s ready to go out and look cute again? Only occasionally though. I can’t break up with my sweatpants. 

What else I’d wear with this:

Tops
Mesh Bodysuit with Puff Sleeves 
Bodysuit with Organza Bow

Jeans
Levi’s Skinny Shaping Jeans
Topshop Black Mom Jeans

Shoes
Snake Print Pumps
The other shoes from the Chanel sweater would look great too!

Bag
Black Wristlet
Black Quilted Chain Bag

Jen’s Styling – Denim Dress

This denim dress is definitely my style! I’ve had denim dresses like this before, but they’re probably a little too short now. This dress is still available at Old Navy.

This dress would be great for a casual day out when you still want to look cute! 

I recently got these shoes from Target, and I’m OBSESSED. They look just like the Chanel espadrilles! 

If it was cooler outside, this denim dress would be super cute with flat over-the-knee boots! 

Because this outfit is relatively simple, I’ll pair it with a more colorful bag with a pattern. For Christmas, my amazing husband got me the Gucci Donald Duck mini shoulder bag. It’s so stinkin’ cute – I love this bag! I can’t wear this when going out with our toddler, because somehow she needs an entire house worth of stuff, but I use this all the time when I’m solo. And by solo I mean picking up groceries once a week – ha! 

This outfit would also be cute with a tote bag so you can carry all of your things! I love the Madewell Transport Tote. It’s great quality, affordable, and super cute! 

If you’re into hats, this outfit would be really cute with one like this from Madewell! I never got into hats before because I thought it would look weird with my side swoop bangs. But now that I’ve grown my bangs out i might need to give hats another chance! 

What else I’d wear with this: 

Bags
Madewell Large Transport Camera Bag
Reversible Tote Bag

Shoes
Elora Mules
Steve Madden Travel Sandal
Steve Madden Hawthone Sandal

Dianne’s Styling – Denim Dress

This dress for me screams “shopping with girlfriends”. I picture it on a girls weekend, strolling through the shops in Savannah. It’s a dress that would travel well. It is a little plain for me, which is why I added the neckerchief. Neckerchiefs seems to ebb and flow in popularity, but I consider them a classic. Because this dress is great for vacation, I paired it with this crochet backpack from The Sak (currently only available in black). I have on espadrilles, but I would also pair the dress with a sneaker or sandal.

What else I’d wear with this:

Shoes:
Leopard print slides – Target
Tie-dye sneakers, as featured in our “Transitional Shoes” blog post

Handbags
Straw Leopard Shopping Tote – Amazon
Ellen Crossbody – Coach Outlet

And here is the final compare….how did we do? Let us know in the comments below!

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