Last updated on January 9th, 2023 at 12:32 pm

Welcome to Volume 2 of How to Wear it At Any Age! If you missed Volume 1, let us give you a quick refresher:

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 or new to us. For this round, it’s the gingham shirt with the puffy sleeves. 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! (Please note: As an Amazon Associate, we earn from qualifying purchases.)

The Challenge:

Here are the items that we chose to style:

Wide Leg Printed Pants

Jen’s Styling – Wide Leg Printed Pants

If you’re like me, the idea of buying patterned pants can be a little intimidating. Not wearing them per se, but being able to put together enough outfits to get my money’s worth. 

These pants from Old Navy are super affordable, and can be treated as a neutral to make so many different outfits! 

I paired these pants with a cute green bodysuit from Dallas & Dottie to show off how cute the pants are. 

A bodysuit or a front-tucked shirt is the way to go with these pants to show them off! 

They’re the perfect length for me to wear some cute sandals and not drag on the ground. 

I love this Beatles tee from Abercrombie, and think it would give these pants a super cool boho vibe. And I really do love the Beatles, so I would wear it. I don’t understand when people wear band shirts and have never listened to the music before. It’s strange. Right?  

Beatles Band Tee
Seamless Tank Bodysuit
Ribbed Scuba Bodysuit

Espadrille slides
Espadrille Wedges
Jean Jacket

Dianne’s Styling – Wide Leg Printed Pants

These pants are the exact same pants as Jen’s from Old Navy, they are just a different print. If you’ve noticed a pattern with us, it’s that I like things a little bolder and Jen likes more neutrals. That’s why we each picked the pattern we did.

The pants are somewhat bright, so I chose to pair them with a more neutral color shirt, also from Old Navy. You can’t see it too well in this image, but there is a slight brown stripe in the pants, so I liked picking up on that color.

I love the straw bag with this outfit. The straw bag, along with the linen fabric of the pants, makes the entire outfit so summery. I bought my bag a couple of years ago at Kohl’s and they are still selling it. So it must have been a best seller!

I am also a big fan of summer jewelry. The necklace I am wearing is from Target and I just love it. I can see me wearing it all summer long. The best part is it’s only $16.99, a perfect price for a summer piece.

I also really like a denim jacket with this outfit. I tried the couple that I own and I didn’t think they looked quite right. They were a little bit long and with the fullness of the pants, it seemed too much. I think a cropped denim jacket that just hits at the top of the waist of the pants would look much better. Here’s one I found on gap.com that I think would be perfect. I like a darker wash with this outfit.

As far as shoes go, I do like a flat neutral sandal but you could also wear a wedge, and believe it or not, I actually own the Espadrille wedges that Jen recommends above. As we mentioned, we don’t tell each other what we’re going to write, so I thought it was funny that she included that pair. I talked about it in my transitional shoes post from a couple of months back, but I have a wide foot. What I’ve found is that if you order shoes early, like these wedges, from target.com, they usually have wide widths – just a little tip if you have wide feet like me!

Gingham Puffy Sleeve Shirt

Jen’s Styling – Gingham Puffy Sleeve Shirt

This gingham shirt gives me picnic vibes, or a summer date night. Traditionally I think of gingham as preppy, but pairing this shirt with ripped jeans and studded sandals gives it a look that fits with my style!

This shirt could be paired with both shorts and pants. With shorts, I’d wear some cute sneakers. And for a date night, some jeans and cute heels or wedges. 

I love the idea of pairing this shirt with a straw bag to play up the picnic vibe. But I don’t have one yet! I have a couple bags that are in pretty steady rotation, but it’s nice to have other options!

Plus, how cute would this top be with a bright pink or red lipstick? 

Mid-length Denim Shorts
Levi’s High-Rise Straight Jeans
Quilted Slides

Studded Strappy Sandals
Mule Heel Sandals

Dianne’s Styling – Gingham Puffy Sleeve Shirt

I will admit it, this one had me a little worried. When I found it online at Loft, I loved it, but wasn’t sure I could pull it off. I decided, for me, since it’s a very trendy piece, that I would pair it with some traditional white skinny jeans and add a pop of color with my handbag.

While I truly believe you can wear anything at any age, I like to wear only one trendy piece at a time. So, I paired the outfit with some classic hoops, making the most outstanding piece of the outfit the shirt. Yes, I know the bag is bright, but at some point the bag would be separated from me and the outfit has to stand on it’s own!

Because I am only 5’3″, I do like a neutral shoe with a cropped pant. I think it elongates my leg. I also like thong sandals – first, because of those wide feet I mentioned and two, I find that the less “shoe” I have on, the longer my legs look!

Our gingham shirt at Loft is almost sold out, so we did find a cute alternative at Draper James. If you’re not familiar with Draper James, the company was founded by Reese Witherspoon. All of the items she sells are adorable and have that “southern charm”, just like Reese.

Keds

Jen’s Styling – Keds
Keds are a classic. Who didn’t have Keds growing up at some point in their life? There’s so many different styles, patterns, collaborations (Kate Spade! Rifle Paper Co.!), that anyone can find the perfect pair for them. 

For me, I’m all about anything classic and neutral that I can dress up or down. 

Dress it up:

Wear these with a midi-length dress, for when you want to look super cute, but also don’t want to wear heels all night. (Side note: do you still wear heels? Do you plan on wearing them again when life gets a little more back to normal?)

Pair it with a jean jacket, or a faux-leather jacket to make it even more sassy. 

Cami Midi Dress
Sleeveless Dress
Button-Front Dress

Dress it down:

Jeans, shorts, t-shirts – these Keds will make any outfit look put together and cute when you’re out and about! 

Cami Romper
Cactus Shirt
Knit Pullover Sweater

Dianne’s Styling – Keds

I love a white sneaker and Keds are the best. The ones we are wearing are the original Champion in organic cotton. They are also a Michigan based company, which hits home for us. I think I had my first pair of Keds in seventh grade (a looong time ago) and I remember wearing them with my lavender striped pants from Sears. I thought I was so cool!

Flash forward and here we are again. As Jen said, they are a classic and they really look good with just about everything. I paired them with this fun striped dress for a little bit of an athleisure look, especially paired with the backpack. (Tip: Keds now also come in wide widths!)

Because Keds are so American to me, I always picture them around July 4th at a picnic. That’s why I picked this fun stars and stripes dress. This would look so cute at a BBQ or fireworks this summer.

And, of course you can’t go wrong with a pair of white denim shorts. I love pastels in the summer (as well as brights) and I think this pink puffy sleeve t-shirt and straw tote just round out the look!

So, what do you think? Let us know your thoughts on how we’ve each styled each outfit! Hopefully we gave you some inspiration!

Want more? Check out our “How to Wear It At Any Age, Volume 1“