Last updated on September 4th, 2023 at 08:34 pm
We are back with “How to Wear it at Any Age” Volume 20! As you may know, we took a little break so Jen would have a great pregnancy and bring little Oli into the world healthy and happy. We are so happy he’s here and Jen know how a wonderful family of four.
But getting a break always gives you time to think and find ways for improvement. So, starting with “How To Wear it at Any Age” Volume 20, our monthly editions will now all have a common theme. Volume 20’s theme is all about transitional dresses you can get on Amazon.
Transitional dressing, we think, is one of the hardest things to style. In a lot of cases you have to be prepared to style the outfit one of two ways. One, if it’s cold and one if it’s warm. But the key thing is that the piece can be worn both ways.
How Does “How to Wear it at Any Age” work?
This is how “How to Wear it at Any Age Volume 20” 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!
Here’s what we’re styling for “How to Wear it at Any Age” Volume 20, from left to right:
Amazon Essentials Women’s Fluid Twill Tiered Fit and Flare Dress in Blue/White Stripe, $34.80
Long Sleeve Sweatshirt Dress in Black, $31.99
T-Shirt Maxi Dress in Green, $36.99
**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 8/19/23.
The Challenge for “How to Wear it at Any Age” Volume 20
T-Shirt Maxi Dress – Dianne’s Styling
To start with, I love the color of this dress. It can easily be worn in both spring or fall. I have a little bit of a hybrid look here. I added the caramel colored belt and bag to add a fall feel to the look, but kept my shoes a little more summery with the wedges.
The belt has an alternate use as well. Since this dress is a little bit “flowy”, I wanted the belt to cinch my waist, which it does perfectly. The belt also adds some gathers to the dress for a somewhat draped look.
SHOP DIANNE’S LOOK: Dress and belt, exact. Shoes and bag similar
DIANNE’S ALTERNATE LOOK:
One of my favorite color combinations is green and purple. When I found this wrap, I knew it was the perfect match. Because of the boldness of the plaid wrap, I kept the booties, bag and hat a neutral color. But I had to throw in the purple belt to cinch the wrap for a more polished look.
This is the perfect cider mill outfit!
T-Shirt Maxi Dress – Jen’s Styling
With long dresses like this one, it’s easy to change it up a little bit without accessories! Tying up the front part of the dress gives it a totally different look. Plus, if the dress is a little on the longer side for you, tying it up means less tripping!
I’m a huge fan of this bag from Uniqlo! I read about it being one of the new “it” bags, so I wanted to try it out. For just $20, I got it in cream and olive green. It’s crazy how much can fit into this bag. I was recently at a baseball game and needed to put my bottle of water somewhere. Into the bag it went with no problem. Alongside my wallet, keys, phone, hand sanitizer and chapstick!
My Nike sneakers are on constant rotation, and work really well with this dress too. Makes the whole outfit comfortable, but still put together.
SHOP JEN’S LOOK: All exact
JEN’S ALTERNATE LOOK:
As it starts to get colder outside, a shacket is a great option for keeping you warm. This flannel coordinates with the colors of the dress, making it look like they already went together.
Plus ankle boots make you look like you’re ready for fall. Tie the dress in a knot in the front to show off your boots!
And if you’re a fan of the Uniqlo bag too, they now have it in corduroy! I’m currently adding to cart for the fall!
Long Sleeve Sweatshirt Dress – Dianne’s Styling
I love this dress. It’s so simple, but that’s what makes it so great. There are so many things you can do with it. I kept the look pretty basic — this would be a “Saturday shopping” outfit. I’m picturing myself walking through our downtown area on a September Saturday sipping on a chai tea latte.
I do like platform sneakers, which these are. I think they are an elevated look (both literally and figuratively!). At 5’3″ they give me a bit of height, but are still comfortable. I added the scarf for a pop of color and kept my bag neutral (but large enough for shopping!).
SHOP DIANNE’S LOOK: Dress and shoes exact. Scarf if similar. My Telfar Bag is available, but they are only made available every so often, so you have to get on their email list to know when the color you want will be able to be purchased.
DIANNE’S ALTERNATE LOOK:
Snakeskin patterns are back on trend again and I love these sneakers with just a touch of snakeskin. The cropped trench coat is a cute alternative to a classic jacket or shacket.
I added the extremely popular belt bag from Lululemon. I have this bag in two colors and have been using them all summer long. They fit your body perfectly and have more room than you would think.
This is a great casual weekend look for meeting friends, running errands, just about anything you can think of.
Long Sleeve Sweatshirt Dress – Jen’s Styling
Sweatshirts are a fall staple, and a sweatshirt dress takes it to another level! Sweatshirts are instinctively casual, but pairing it with my trusty combat boots and faux leather jacket make this a put-together and edgy look.
Plus, it’s super comfortable, which is a big time bonus.
SHOP JEN’S LOOK: Dress exact, rest similar
JEN’S ALTERNATE LOOK:
I love anything and everything black and white (like these Nike Dunk dupes from Target, what?!). And black and white go with just about anything too like this army green jacket. It breaks up all of the black in the outfit, while still looking cohesive.
I also love the houndstooth pattern on this shopping tote! Patterns like this give any outfit a little extra something-something!
How To Wear it at Any Age Volume 20
Tiered Fit and Flare Dress – Dianne’s Styling
This dress was a real pleasant surprise for me. It fits so nicely and is so comfortable. I wish I had gotten it sooner so I could have worn it all summer. I went with a classic denim jacket, I love bringing the two different blues together. Once again, I stuck with sandals for a more summery feel and added the neutral cross body bag.
This dress can be worn for so many occasions – brunch, shopping, even a bridal/baby shower. Oh, and did we mention the vertical stripes? They have a great slimming effect!
SHOP DIANNE’S LOOK: Dress and shoes exact, jacket and bag similar
DIANNE’S ALTERNATE LOOK:
I wanted to try a different look and so I went with the white cardigan duster. It’s a chic look, even with the sneakers. I added the navy bag to keep the accessories in the blue family without being too “matchy-matchy”. The long pendant provides a great finishing touch.
This outfit can be worn anywhere, even a casual day in the office.
Tiered Fit and Flare Dress – Jen’s Styling
When I was putting together this look, these boots caught my eye in my closet, and I instantly thought about adding the hat. In northern Michigan is Traverse City, an area with amazing wineries. Visitors tour different wineries, doing wine tastings, and enjoy the beautiful scenery.
This outfit reminds me of the stylish women I see doing tastings, with their girlfriends. One of my best friends wore a hat similar to this on one of our trips, and I remember thinking how great she looked!
SHOP JEN’S LOOK: Dress exact, hat and booties similar
JEN’S ALTERNATE LOOK:
Swapping out the accessories turns this dress into the perfect classic, preppy ensemble. The textured jacket reminds me of Chanel, and is super classy. The ballet flats and structured bag add even more elegance.
This looks like an outfit you’d see on a woman at a country club, and be instantly envious of how pretty and well dressed she is!
So, which outfit is your favorite? Let us know in the comments.
Did you know that we also have a sister series, “Beauty At Any Age”?
Similar to the How to Wear It series, we cover all different beauty topics from the same multigenerational perspective.
Our most recent post was all about press-on nails!
You can check in out in our “Beauty At Any Age” section.
