How to Wear it at Any Age Volume 19

For “How to Wear it at Any Age” Volume 19, we’re thinking ahead to “April showers”. April is just a few weeks away and we want you to be ready to go. In that vain, we’ve’ve included a great trench coat and rain boots and for when the weather starts to break, we’ve got a perfect transitional maxi dress for you.

We’re continuing our “At Any Age” as Jen’s pregnancy progresses, as it makes sense. There’s only two months to go. You’ll see in this edition we’re both styling rain boots – that’s just one way we’ll continue in the short term. So stick with us – we’ve got lots of ideas on how to keep you inspired! We might take a short break when the baby arrives, but we’ll definitely be back!

This is how “How to Wear it at Any Age Volume 19” 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! 

How to wear it at any age volume 19

Here’s what we’re styling for “How To Wear it at Any Age” Volume 19:

Trench coat from Amazon, $59.99. We decided to go with two different colors for this classic piece. Dianne already had khaki trench coat and wanted some more color. Jen wanted to update her khaki trench coat, so she went with the ultimate classic color.

Chelsea rain boots form Target, $24.99. Cute and functional

Royal blue striped maxi dress from Amazon, $33.98

**This post contains affiliate links and we will be compensated if you make a purchase after clicking on our linksHowever, we only recommend products that we truly love. Amazon prices are as of 3/13/23.

THE CHALLENGE FOR “HOW TO WEAR IT AT ANY AGE” VOLUME 19

HOW TO WEAR IT AT ANY AGE VOLUME 19: TRENCH COAT

JEN’S STYLING

wear it at any age

Shop Jen’s Look: Jacket and purse exact, everything else similar

I had a trench coat I bought in 2010 in Paris at Zara (before Zara was in the US), that I wore the absolute heck out of. 

Unfortunately, wearing it as often as I did there’s a lot of wear and tear. Plus, I’m definitely not the same size now as I was back in 2010, Regardless of baby. So it’s due time to get a new trench! 

My mind is already set on spring, where there’s a hint of the weather starting to get warmer. And a trench coat is perfect when there’s still a little chill in the air, and there’s always a chance of rain. 

Not a total surprise, but I love the look of a tan/camel trench coat with an all-black outfit. Depending on the weather, I’ll wear black pants and a black blouse, or a sweater if it’s a little bit colder. 

As for a bag, I don’t always stick to just black. I consider most of my staple bags (Louis Vuitton or Goyard) a neutral, that will go with just about anything. 

JEN’S ALTERNATE LOOK:

clothes collage for trench coat

To make this trench coat unequivocally spring, pair it with a flowery dress! Personally, I would get a dress a little longer than the trench, to avoid accidentally looking like a flasher! Or, I just wouldn’t belt the jacket, and leave it open. 

Ankle boots, slides or sandals would all look great, depending on the weather! And don’t forget an umbrella before leaving the house!

Dianne’s Styling

How to Wear it at Any Age Volume 6

Shop Dianne’s Look: Coat and jeans exact, everything else similar

If you had to ask me what’s the biggest difference between Jen’s and my style I would have to say color vs. neutrals. Jen prefers neutrals and I am all about color.

For me, I think my love with color started with the way my mom dressed me as a child. She dressed in lots of colors and as a result did the same with me. So I just got used to it. I also think I look better in brighter colors.

So, when we found these trench coats, it was natural for Jen to want to go with the classic khaki/tan and i wanted something a little more unique and bright. I picked the yellow on purpose because it reminded me of the classic fisherman rain slicker! If it’s going to be rainy and gloomy, let’s add some sunshine.

DIANNE’S ALTERNATE LOOK:

wear it at any age trench coat

What I love about the bright yellow color for this trench coat is that it’s easy to make it part of your outfit. Blue and yellow is one of my favorite color combinations so I specifically looked for a dress with that color combination. I also like a white sneaker, especially in early spring. It’s a fun and casual look.

Chelsea Rain Boots

JEN’S STYLING

How to wear it at any age rain boots

Shop Jen’s Look: Shoes exact, everything else similar

These aren’t your typical knee-high rain boots. They’re easy to incorporate into any outfit you’re wearing. 

Comfortable and nice enough to wear into work on a rainy day. 

The primary way I would wear these is with jeans, with them cuffed right where the boot stops. 

The top and jacket depend on the weather, but I always consider stripes a neutral. 

In this instance, I’ve added my trusty faux leather jacket, but the look can be changed up with any jacket! 

JEN’S ALTERNATE LOOK:

rain boots collage

These boots are perfect for running weekend errands too, when you just don’t want to wear real pants. 

Pair with leggings and tall socks scrunched over the top of the boots. A sweatshirt, a coat that works for the weather, and you’re all set for going out! 

A backpack or a belt bag will keep you hands free when you decide you don’t need a cart at Target, because you’re just getting “a couple things”. 

DIANNE’S STYLING

how to wear it at any age

Shop Dianne’s Look: Boots, jeans tee and umbrella exact. Everything else similar.

I have to admit that Jen had these boots first and as soon as I saw them, I had to have them. What I loved about them was that you couldn’t tell they were a rain boot. They just looked like a cute chelsea boot that you could wear with pretty much anything.

I paired them with an all black outfit to show how well they can fit with anything. I love pairing the faux leather black shacket with them.

DIANNE’S ALTERNATE LOOK:

wear it at any age collage

I love this plaid wrap with the rain boots. It’s a perfect transitional piece for a chilly rainy day. Almost like a warm hug. And back to those bright colors on a dreary day.

One of my favorite types of umbrellas are clear bubble umbrellas. You can carry them low and over your clothes and still be able to walk and see! And if you use a bubble umbrella with this outfit, you can still see that bright wrap!

How to Wear it at Any Age Volume 19: Striped Maxi Dress

Jen’s Styling

maxi dress

Shop Jen’s Look: Dress and jacket exact, shoes similar

I had a maxi dress that was in pretty steady rotation during my first pregnancy, and this one is going to be the same. 

This isn’t a maternity dress, but it works before and after baby because it’s stretchy and comfortable. 

I’ll pair this with a jean jacket because it’s still a little chilly outside, and some comfortable slides! 

I’m at the point right now where I’m all about comfort, but this maxi can be dressed up and still comfortable. 

JEN’S ALTERNATE LOOK:

maxi dress collage

Mix up this maxi dress look by swapping the denim jacket for a white button down! Tie the shirt at your waist, for a summery and preppy look. Add a straw bag and strappy sandals to turn up the preppiness. 

Feel like you’re getting ready to go out on the boat, even if you’re nowhere near water! 

To make this trench coat unequivocally spring, pair it with a flowery dress! Personally, I would get a dress a little longer than the trench, to avoid accidentally looking like a flasher! Or, I just wouldn’t belt the jacket, and leave it open. 

Ankle boots, slides or sandals would all look great, depending on the weather! And don’t forget an umbrella before leaving the house!

DIANNE’S STYLING

how to wear it at any age

Shop Dianne’s Look: Everything exact except shoes, which are similar.

I originally planned to wear a white denim jacket with this dress but changed my mind and went with a more feminine look. I love how the cropped cardigan stops just perfectly at my waist. It made adding the belt seem like a natural fit.

This dress can easily go from early spring to late summer. You can wear it with or without a jacket/sweater and add some fun summer jewelry and flat sandals to make it more casual.

DIANNE’S ALTERNATE LOOK:

how to wear it work collage

I think this dress has lots of potential to be worn to the office. Swap out the white cardigan for the white blazer, add some chunky jewelry and heels and top it off with a structured handbag. Perfectly office chic!

Do you have a favorite look that we’ve shown here? Let us know in the comments below.

And be sure to check out out entire “How To Wear it at Any Age” series!

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