How to Dress Up a Polo Shirt

I appreciate each and every share. Thank you!

How to Dress up a Polo Shirt for women over 40

How to Dress Up a Polo Shirt

It may not seem possible to think about how to dress up a polo shirt. But we were up for the challenge.

Quote of the day: “Perhaps a man really dies when his brain stops, when he loses the power to take in a new idea.” George Orwell

I love it when I can relate a quote to something I’m writing about regarding fashion and style. And since our subject today may be a little out of your comfort zone, I thought it was perfect.

Last year, when a reader, Jill, requested some ideas for styling a polo shirt, I couldn’t accommodate her because I didn’t have one. So my mission was to buy one and have us figure out how to dress up a polo shirt this year. We started with pairing this top with print pants.

How to Dress up a Polo Shirt for women over 50

And the reason I think this could be considered a new idea, is because I think of a polo shirt as a casual, masculine piece of clothing. And a skirt? Exactly the opposite. I remember when I read about dichotomy in an outfit, meaning pairing two opposite styles. And I think it’s a great way to make any item modern.

The three of us used this same idea when with our pairing of graphic t-shirts 2 years ago.

Jodie’s (50+) Outfit

How to Dress up a Polo Shirt with a backpack

Skirt: DownEast from Trendz c/o (similar here)~~Top: A/X-thrifted but DIYed by me (similar here)~~Shoes: Chinese Laundry (similar here)~~Necklace: thrifted (similar here)~~Earrings: (similar here)~~Purse: (similar here)

How to Dress up a Polo Shirt for midlife women
How to Dress up a Polo Shirt by DIY lace around the edges

Why I Wore This Outfit

If you saw my collection of print skirts, you might laugh. I must have an affinity for them, so it wasn’t hard to find one that would look good with the striped polo. These small stripes are an easy way to print mix because from a distance, they look like a solid.

I wore this skirt when we had our summer fun last year at the local boutique. I think I like it better with some contrast on the top half of my body instead of matching the pink like I did last year.

How You Could Change This Outfit

If I was at home, I probably would have changed my purse to something different. A bright pink purse would have been more my style for this outfit.

I chose the pink heels to act as a neutral with the outfit. If I had a pair of pale pink flats, I would have worn those instead. Not that these heels are uncomfortable, but the design on the front makes it feel busy.

What Makes this Work

I absolutely love these kinds of skirts. They are a cotton blend with spandex in them, and are like leggings in a skirt form. If you notice the “front tail” on my shirt, I did use a rubber band to make my shirt fit better. I recently made a video regarding 3 tips on how to make your shirt fit better if you find that some tops are too boxy.

Interesting Tidbit

Like I discussed in our previous post on how to dress up a polo shirt, I was wrestling with how to make this color look better on me since it’s not one of “my colors.” Therefore, I chose a necklace and earrings that are better for my coloring. This multi strand necklace was only $1 at a local thrift store when they had one of their blowout sales.

Nancy’s (60+) Outfit

How to Dress up a Polo Shirt with a denim skirt

Skirt: Prana-thrifted (similar here)~~Top: Tommy Hilfiger (similar here)~~Shoes: Impo (here in other colors)~~Necklace: (similar here)~~Earrings: (similar here)~~Purse: (similar here)

How to Dress up a Polo Shirt in the Summer
How to Dress up a Polo Shirt in Vail

Why Nancy Wore This Outfit

This skirt has been a go to for Nancy since we found it in Frisco at a consignment shop. The denim skirts of nowadays, have spandex and stretch in them just like jeans, so they tend to be super comfortable.

Even though this one is a pencil skirt, it still has lots of give and it’s easy to walk in because of the slit in the back. Heck, she’s even worn it in the winter with leggings. And the best thing about wearing it with leggings? It doesn’t cling and stick together like the knit skirts.

How You Could Change This Outfit

Since the denim skirt tends to be more casual, it’d be a perfect time to wear your fun sneakers with a skirt. We’ve tried this concept in the past, but I’m not sure it was totally successful. I think it depends on the skirt and the sneakers to look modern and not frumpy.

I always think that a modern sneaker is a smart purchase because of the comfort. The embroidered ones are so lovely, gingham is very on trend right now, along with metallic pink to add a touch of pizzazz to jeans or a skirt.

What Makes this Work

This is a perfect example of keeping the outfit more casual, even though you’re wearing a skirt. Seriously the denim skirts are having their day almost as much as denim in everything else. I truly believe that skirts can be cooler in the hot weather. Even though denim isn’t as lightweight as other materials, it does provide the air conditioning for your legs.

Interesting Tidbit

Nancy got this necklace at a craft fair in Portland, Oregon. She loves that the beads are sewn together with a strong brown thread. Obviously she chose the necklace to match the polo shirt for this outfit, but I think that this turquoise color can go with white, pink and even black wonderfully too.

Charlotte’s (80+) Outfit

How to Dress up a Polo Shirt stylishly for women over 70

Skirt: Mom made it (similar here)~~Top: Lady Hathaway (similar here)~~Shoes: Sonoma (similar here)~~Earrings: Target (similar here)~~Bracelet: (similar here)~~Purse: (similar here)

How to Dress up a Polo Shirt for women over 80
How to Dress up a Polo Shirt with a print skirt

Why Charlotte Wore This Outfit

My mom is a matchy matchy girl through and through. So when she knew she would wear the green polo shirt, she looked in her closet for a matching skirt.

The shoes and purse are more of a turquoise green/blue, yet they add a different color mix to the equation. Just like I talked about with Nancy’s turquoise necklace above, I think that turquoise is such a versatile color.

How You Could Change This Outfit

I think with a matching top and skirt like this, there are a couple of options for your shoe choice. My mom went with a contrasting color with the turquoise. Or you could play it safe with a neutral flat.  With the neutral option, then the focus is primarily on the top and skirt.

Another thought would be to choose something bright like a yellow sandal. The three of us all have yellow shoes in our closet, so we’ve talked about how they can be worn with so much.

What Makes this Work

This shape of skirt is really flattering on almost every body type. It’s so easy to walk and sit in, so the comfort is there too. And when the bottom half of your outfit has more volume, it’s always good to wear a tighter fitting top like my mom is doing.

Interesting Tidbit

My mom made this skirt many years ago, and has worn it a couple of times on the blog. In fact, the first time isn’t much different than this outfit. Which goes to show how we tend to style the same things over and over. My favorite is when I twisted her arm to pair it with bright blue.

She saw this palm leaf material on a sidewalk sale and then when it was still there 2 weeks later, she figured it was meant to be.

How to Dress up a Polo Shirt with different styles

Tips & Tricks

I feel like I may be saying the same thing over and over. And that could be because these shirts are somewhat like a t-shirt. Maybe they aren’t the most exciting shirts in your closet. So in that case, you make other items the focal point.

That means, either add some great accessories, wear some fun heels, wear lively bottoms, or even add an interesting topper. It may not be rocket science, but it can add some glam to an item that isn’t everyone’s favorite piece.

How to Dress up a Polo Shirt with different skirts

We stayed in Vail for these photos after our tour around the Betty Ford Alpine Garden. Check out the ski run behind us. Since it’s just the beginning of summer, there is still snow on some of the mountains.

The ski towns have just as much going on in the warmer months. This day when were were here was an interesting festival for outdoorsy people. Many will ride their mountain bikes down the ski trails, and then there are the indoor people like us, that just love to walk around and visit the restaurants and stores.

The Facts

If you liked any of these photos, it would help me if you pinned them to your own Pinterest board. It’s one way that others can see our outfits. 

Even if you wouldn’t consider purchasing your clothing online, it can be helpful to look through my links to see what is available! It certainly doesn’t hurt my feelings, if you click on them but don’t like them. Just so you know, one of the ways I make money from this blog is through these linked items.

Keeping in Touch

I would feel extremely thankful if you sign up for the emails to let you know when a post goes live. Just add your email to the pink box that says smile and click here. I only use this email list to send out a notice for my posts, and to offer my regular readers a chance at a survey now and then. In the future, I plan to incorporate special offerings to my email subscribers. 

It’s so helpful to me if you follow me on any social platform that you’re on like Facebook, Pinterest, Instagram, You-Tube

And if you’re new to my blog, you can always see our outfits organized by categories, here. Don’t forget to check out the deals & discounts too, on this page.

Also, feel free to Shop My Instagram items.

shares