Last updated on January 9th, 2023 at 12:16 pm

It’s time for our holiday edition — it’s “How to Wear it at Any Age” Volume 16. We’ve got three looks that are perfect for the holidays, but not solely for the holiday season. Each of these three pieces you can wear for other occasions throughout this year.

But, for this edition, we are styling them with the holidays in mind. Thinking ahead, the red dress will be perfect for Valentine’s Day and the green moto jacket will provide a stylish look for St. Patrick’s Day. And that’s just in the next three months!

This is how “How to Wear it at Any Age Volume 16” works: We decide together on the 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. Sometimes we will style things very similar and sometimes very different. But we hope in all cases we give you some style inspiration, no matter what your age or life stage! 

**Please Note: This post contains affiliate links and we will be compensated if you make a purchase after clicking on our links. However, we only recommend products that we truly love. Amazon prices are as of 12/12/22.

The Challenge for “How to Wear it at Any Age” Volume 16

Here are the three pieces we are styling for “How to Wear it at Any Age” Volume 16.

Black Plaid Faux Fur Cape from J. Crew Factory, $69.99

Red Calvin Klein Sheath Dress from Macy’s, $66.99 (on sale as of 12/12/22)

Faux leather Green Moto Jacket by Scoop at Walmart, $27 (more on the Scoop brand below)

How to Wear it at Any Age Volume 16: Black Plaid Faux Fur Cape

DIANNE’S STYLING

SHOP DIANNE’S LOOK: (Cape, leggings, boots exact, all other items similar)

One of first great things you’ll notice is that this cape can be used in so many ways. It looks as great with leggings as it would with a dress. I wanted to make this an “elevated casual look”. One that looks chic but is still very comfortable.

I have one just a simple black tunic sweater on underneath because the cape really is the focal point. You’ve probably seen me do this in other posts, but I just love a pop of red with black and white. I also like the red purse because when I take off the cape, I still have a great accessories that provides some color to my outfit.

I’ve had my red Coach train case for several years and Coach does not sell it anymore. I did find another bag I love with the bow which I think would also fit nicely with the outfit. But if you do love my train case, I did find it on Poshmark, if you’re interested.

DIANNE’S ALTERNATE LOOK:

I’ve always loved winter white but for some reason I haven’t worn it in a while. When I was creating this look, it really made me want to find an all white outfit (I would wear this one for sure).

This is another outfit that could easily spill into January. I can see this outfit walking around Park City, Utah or Aspen, Colorado.

JEN’S STYLING

I’ll preface all my outfits by saying because I’m pregnant, I’m trying to not buy a ton of new stuff that I can’t wear much longer. So things like my jeans, are maternity, and I won’t link them (but if you are pregnant, send me a message!). And a lot of these things I’ve had, so I’ll link non-maternity styles to give you a similar look! But it goes to show, you can create so many different, and gorgeous looks, with what you already have!

SHOP JEN’S LOOK (Cape and boots exact, all other items similar)

Wearing a cape feels glamorous, especially with this faux-fur collar! I wore a cape on Thanksgiving, and I felt like it added an extra touch to my comfortable food-eating outfit! 

I feel the same way about this cape! It’s great for keeping you warm and making any outfit look instantly fancier. 

Coincidentally, I got this top from my best friend a couple years ago and the earrings for her wedding seven years ago. Velvet feels so fancy for the holidays, and there’s so many gorgeous velvet options from tops to dresses!

JEN’S ALTERNATE LOOK:

I thought this sweater dress would look so cute with the cape, plus the long gloves make a statement when getting to where you’re going! 

A necklace won’t show up as well, so go all out with big dangly and sparkly earrings! Plus these cute polka-dot tights and knee-high boots! 

Don’t forget a pair of slippers so you’re not slipping and sliding in just tights, or tracking in snow and mud by keeping on your boots!

How to Wear it at Any Age: Red Sheath Dress

DIANNE’S STYLING

SHOP DIANNE’S LOOK: Dress and shoes exact, all other items similar)

I love red. A lot of people think it can be too much, but I think it looks great, all year long. I love it as much in the summer as I do at the holidays.

What I love specifically about this dress is that it’s simple, yet the sleeve detail gives it just a taste of fancy! The puff sleeve add some interest without going overboard.

My necklace is from “How to Wear it at Any Age Volume 6”, a year ago. Even though it’s a piece that you’ll only wear a few times each year, it’s great to have for when you need it. Wearing it with the dress makes the entire outfit scream “Christmas”, which was what I wanted.

Come February, I can change the jewelry, switch out the pumps for boots and have a great Valentine’s Day look!

DIANNE’S ALTERNATE LOOK:

This is definitely a holiday look, maybe something out of a Hallmark movie. The tartan plaid coat with the fur cuffed gloves would put anyone in the holiday spirit. I’m dressing the look down a little bit with the black boots, which I would pair with black tights.

I own these exact boots and highly recommend them. I have wide feet and these are extremely comfortable (I did go up a half size).

JEN’S STYLING

SHOP JEN’S LOOK (Dress, shoes and jacket are exact, all other items similar.)

This red dress is such a holiday classic! The color is perfect! Plus the patterned tights, boots and faux-leather jacket make a gorgeous holiday party look!

I’ll tell you a little behind the scenes info – these tights definitely aren’t maternity. Had to roll them down under my belly to make them fit! Ha!

I wore the same dangly earrings, but you could mix it up with some hoops, a bunch of rings, or a sparkly necklace.

JEN’S ALTERNATE LOOK:

I love that this coat with a pattern breaks up the solid color a bit. The jewelry adds sparkle with both the necklace and earrings, plus these shoes! I’m OBSESSED with these shoes, and I’m sort of devastated they don’t have them in my size. 

I’m trying to get my sister to buy them, so at least someone has them! 

Plus, another pair of fuzzy slippers to stay comfy! Even though I LOVE the shoes!

How to Wear it at Any Age: Faux Leather Green Moto Jacket

DIANNE’S STYLING

SHOP DIANNE’S LOOK: (Jacket, shoes and earrings exact, all other items similar)

We mentioned about that we’d give more details about this jacket and why we love it (especially for only $27, although it is selling quickly). Fashion Designer Brandon Maxwell became the Fashion Director at Walmart a couple of years back and created two clothing lines for them: Free Assembly and Scoop.

This jacket is part of the Scoop line and we love it. It is incredible well-made for the price and very soft. It’s a steal. It’s another item that is perfect for Christmas but you’ll be able to wear it all year long.

My turtleneck is old, but I would recommend this one from Amazon, which I linked to above. It’s the same turtleneck that I talked about in this article on people.com. The only reason I didn’t wear it in the photo is that I have it in other colors but not black (how does that happen?)

My favorite part of this outfit, as you can probably guess, is the shoes. The jacket and the shoes are all I need to make a basic black outfit festive.

DIANNE’S ALTERNATE LOOK:

I love green and navy together and black watch plaid is a great pattern for the holidays and beyond. This jacket can be dressed up or down and jeans are always a great pairing with a moto jacket. You can always go with a more monochrome navy look and add a scarf for a pop of color.

JEN’S STYLING

SHOP JEN’S LOOK (Shoes and jacket are exact, all other items similar.)

I’ve talked about my favorite faux-leather jacket for probably at least a year now (see outfit above), so this jacket I naturally gravitated to! 

There’s a couple sweater dresses in this post, and I love them for the holidays! They keep you warm, and are super easy to dress up and down. Plus, you’re actually comfortable wherever your get-together is. Eat whatever you want! No one can tell!

JEN’S ALTERNATE LOOK:

I know the green jacket and red plaid are very Christmas-y, but go with me! A look I absolutely love is buttoning up the top all the way up, and wearing a chunky and sparkly necklace under the collar. 

I have these boots in the tan color, and I love them! Super comfortable, and love the fur trim details. 

What’s your favorite piece of the three and how will you style it? Let us know in the comments below.

And, if you want more “How to Wear it at Any Age”, check out the entire section on the website.