Last updated on January 9th, 2023 at 12:25 pm

We’re back with How to Wear it at Any Age Volume 7 – our Holiday Edition! We’ve got three different looks that you can wear all throughout the holiday season.

This is how “How to Wear it at Any Age Volume 7” 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. 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.

The Challenge for How to Wear it At Any Age Volume 7

Here are the items we’ve selected for “How to Wear it At Any Age Volume 7”:

Green Puff Sleeve Dress

We found this green dress back in August and knew it would be the perfect holiday dress, especially in this beautiful emerald green color. Since we did purchase it back in August, there are only limited sizes still available. However, we are also including a link to a very similar dress, also by Calvin Klein, in the same green color and puff sleeve (it is called Malachite). It is a sheath style instead of an A-line style.

The original A-line dress is $89.98 and the sheath style is currently $93.80 on sale.

Plaid Leggings

Plaid is always a great option around the holidays and we found this great pair from Kohl’s of all places! What we liked about them is the navy gives you a little different look for the holidays, but it can still be festive. We found these in the juniors department so we initially thought we would have to size up, but we were able to stay with our usual size. If you are in between sizes, I would still size up. They are $21.99

Velvet Blazer

The velvet blazer we are styling is no longer available (and we only got it a couple of weeks ago). So we are linking to a blazer that is very similar and one that you could easily style in the same way. We found this one at Mango for $120.

**Please Note: This post contains affiliate links and we will be compensated if you make a purchase after clicking on our links.

Our styling for the Holiday Edition:

Green Puff Sleeve Dress – Dianne

I decided to combine a little bit of old with a little bit of new with this dress. Let’s start with the “new”: the puff sleeve combined with the A-line skirt is a very on-trend contemporary look. The “old” I added was wearing my mother’s vintage rhinestone jewelry. I remember her wearing these when I was a little girl.

I actually could immediately smell here perfume as soon as I put the necklace on. In fact we talked about how scents can invoke memories in our post “Scents of Smell” from a few months back.

I also went with a traditional pump but with another modern twist – the block heel. If you’re going to be standing at a cocktail party for a while, you’ll want some extra support. I added the shoe jewelry clips for a festive touch that I got at White House Black Market. I love their accessories. We talked about their faux-fur cuffs in our “Gifts for Her” Gift Guide and we just added these to the guide as well.

I bought these a couple of years back – they don’t have the same ones anymore, but you can see the ones they have HERE. I finished the look with the plaid wristlet from Draper James and “holiday” red lipstick.

Green Puff Sleeve Dress – Jen

I love this dress for a more “traditional” holiday look. It’s the perfect Christmas-y color, and looks great with my red lipstick! 

I paired the dress with opaque black tights and ankle boots since it’s about to get cold in Michigan! And this beaded clutch also gives it a sparkly touch. But you can add some sparkle with a statement necklace or some dangly earrings too! 

Plaid Leggings – Dianne

This outfit that I put together is a little different for me, but I like it. A couple of months back Target had one of their designer collaborations. It’s always difficult to find these items both online and in-store, so when I saw this navy faux leather top by designer Rachel Comey in my size at my local Target, I knew I had to grab it and figure out how to wear it later! And these navy/red plaid leggings ended up working perfectly!

Shoes were the thing that I struggled the most with this outfit. I own some navy suede booties but it was a little too “matchy-matchy”. I thought a casual/boot look would be the best optionso I decided to go with these gray suede booties. A more dressy shoe would have also been an option, but I don’t own a dressier shoe option that I really like. There is a link to the booties below but as of this writing there were just a few sizes still available.

Since I couldn’t really wear a necklace with this top, I opted for some large festive earrings. I love the Sugarfix Baublebar earrings at Target. They don’t have my exact pair but they do have similar pairs that you can shop from the link below.

Plaid Leggings -Jen

These look like dress pants, but SURPRISE they’re actually leggings and super comfortable! They can be dressed up for a holiday party, like I did here. Or you can dress them down for a holiday at home, and still look stylish. 

I paired mine with some patent heels and a sweater, plus a cute bag, for a look that will make everyone jealous when you tell them you’re actually wearing leggings. 

Velvet Jacket – Dianne

This is another outfit when I went to the depths of my closet to find something to wear with this velvet blazer – and it’s the booties. Another purchase from Target from a few years back. They were on clearance after Christmas and it was another one of those “buy it now, figure it out later” purchases.

I made the shoes the focus of this outfit because I find that velvet is so pretty on it’s own that I didn’t want to add a lot of accessories to it. I already owned a velvet tank and I do like the “velvet on velvet” look. But I did want to keep the neckline simple, so I added some sparkly hoops to go along with the booties. I also added a subtle beaded clutch to round out the outfit.

These booties are no longer available but you could substitute them with leopard, snakeskin or even crystal booties to get a similar look. Here are a couple of options:

Snakeskin Stiletto Booties at Macy’s

Leopard Stiletto Booties at Macy’s

Crystal Stiletto Booties at Nordstrom

Velvet Jacket -Jen

This jacket is so festive for the holidays, the material is perfect! If you’re wearing this to a holiday party, keep in mind it might get warm, so you don’t want to wear anything too heavy under the jacket. Plus, if you wear a sweater, will you even be able to lift your arms for eating and drinking? 

This silk tank is so pretty, and perfect for layering with this jacket. You could wear a bunch of dainty necklaces layered together, or one big statement necklace. 

And because the outfit is neutral, you can wear any makeup you want! Bold shadow or bold lips look amazing!

Let us know your thoughts in the comments below. Do you have a favorite look? Let us know if there’s something you’d like to see us style in an upcoming edition!

If you liked “How to Wear it At Any Age Volume 7”, then be sure to check out Volumes 1-6 at THIS LINK.