Ann Taylor Try-On: Elevated Casual Outfits for Women Over 50

I stopped by Ann Taylor recently for a try-on, and this collection surprised me in the best way. I shop enough to know that some collections look wonderful hanging on the rack but don’t make much sense for the life I actually live. I’m not going to cocktail parties every Tuesday night, but I also don’t want my entire wardrobe to consist of T-shirts and leggings. Lol!

This collection seemed to land right in the middle. Everything felt elevated without necessarily being dressy, and that’s a category I can use.

I found linen blends, interesting prints, trouser-inspired denim, and more structured pieces that could work for lunch, church, dinner, vacation, or just one of those days when you want to look a little more put together.

And since this was a real dressing-room try-on, not everything fit perfectly. I’ll tell you the sizes I wore, what I would change, and what I thought was actually worth a second look.

One quick note before we get into the outfits. Yes, I know some of the pants and jeans are too long on me in these photos. I was wearing my favorite NAOT sandals for the try-on and obviously didn’t have my shoe closet with me. If I were styling these at home, I’d wear a platform, wedge, or another shoe with some height. If I wanted to wear them regularly with flatter shoes, I’d have them hemmed.

Now that we’ve saved everyone from worrying that I’m planning to sweep the sidewalks with my jeans, let’s look at the clothes. Lol!

A Black Linen Blend Top With Statement Floral Pants

This outfit immediately caught my attention because those pants aren’t exactly trying to blend into the background. I could see wearing this for dinner on vacation, a nice lunch, or an occasion when I wanted to look special without putting on a dress.

The Wide-Leg Paperbag Pant in Floral Linen Blend features a large black-and-cream floral print, but I think the neutral colors keep it from looking overwhelming. They’re statement pants, but they’re surprisingly easy to style because a simple black or cream top is really all they need.

I’m wearing a size 8, and I liked the fit through the waist and hips. The wide legs give the pants plenty of movement, and the tie waist adds some definition. I also think the tie helps keep all that volume from looking shapeless. They were too long with my flat sandals, but I’d solve that with a platform or wedge. If you’re committed to flats, you may need to have them hemmed depending on your height.

I paired the pants with the Black Bubble Hem Top in Linen Blend. I tried a Large, and it was too roomy on me. I would buy a Medium instead. That’s especially important with these pants because there’s already a lot of volume on the bottom. I prefer the top to fit a little closer to my body so I’m not wearing something loose and oversized from my shoulders all the way to my feet. The black also gives your eye somewhere to rest and lets the floral print be the focus.

One Animal Print Linen Top, Two Very Different Jeans

This Animal Print Boatneck Top in Linen Blend was one of those pieces I liked much better once I put it on. This is the version I’d choose for a casual lunch, shopping, or an everyday outfit.

I’m wearing a Medium, and the fit was good. I especially like the softer cream and camel animal print. You still get some personality from the print, but it doesn’t scream LEOPARD from across the room.

The boatneck makes it look more polished than a basic sleeveless top, and the linen blend makes it a good transition piece for this time of year. I’m mentally moving toward fall long before the thermometer is ready to cooperate.

I tried the top with two different styles of jeans, and this is a good example of how changing one piece can completely change an outfit. First, I paired it with the Wide-Leg Jean in a size 10.

These have a relaxed silhouette and a medium blue wash, so they make the animal print top feel much more casual. I like that the leg is wide without looking enormous. There’s a difference between “wide-leg jeans” and “I appear to be standing in two denim sleeping bags.” Lol!

These were too long with the flat sandals I was wearing, but I’d pair them with a platform or wedge at home. I could also see wearing them later with a shoe or boot that gives me some height.

With the Trouser Jeans

For dinner, church, or somewhere I wanted to look a little nicer, I’d probably choose the trouser jeans. For running around during the day, I’d reach for the more relaxed wide-leg pair. The Trouser Jean in a size 8 looks much dressier with the same top.

These are still jeans, but the trouser shape gives them a more polished look. The long, fluid leg almost makes them look like traditional trousers from a distance. Again, they were too long with my flat NAOT Sandals. With a platform or wedge, I think the proportions would be much better.

This is exactly what I mean when I say this collection feels elevated but not necessarily dressy. I’m still wearing a sleeveless top and jeans. Nothing about this is complicated. But the shape of the denim makes the outfit feel much more intentional.

Same leopard top, completely different mood.

A Plaid Peplum Vest That Feels Like Fall Without the Sweater

The Plaid Crew Neck Peplum Vest might be one of my favorite pieces from this try-on. This is one of those pieces you could wear on its own now and layer later when temperatures finally cool down. It gives you plaid, structure, and those richer colors we start wanting as fall approaches, but you aren’t standing there sweating in a sweater while it’s still 85 degrees outside. I’m wearing a size 10, and I liked the fit.

The slight peplum gives the vest some shape through the waist without making it tight or overly fitted. I also like the gold-toned buttons with the menswear-inspired plaid. That little contrast keeps it from looking too serious.

I first styled it with the Wide-Leg Jeans in a size 10. The light color makes the tailored vest feel much more casual, which is probably how many of us would wear it most often. I could see this with loafers or flats once the jeans are hemmed to the appropriate length, or with ankle boots later in the fall.

I also think this combination proves that a structured piece doesn’t have to equal “office clothes.” The jeans take care of that.

The Vest With Trouser Jeans

Then I switched back to The Trouser Jeans in a size 8, and this was probably my favorite way to style the Peplum Vest. I’d wear this combination to church, lunch, dinner, or anywhere I wanted to look pulled together without feeling overdressed.

The longer trouser silhouette balances the slight flare of the peplum and gives the whole outfit a cleaner, more polished appearance.

If you don’t wear traditional dress pants very often anymore, trouser jeans can be a nice compromise. You still get the familiarity of denim, but the cut makes them look more refined.

The Palm Print Linen Dress

And then there’s the dress. The Palm Tree Print Column Midi Dress in Linen Blend has a breezy, almost resort-like feel, but the column shape keeps it from looking like something you’d only wear on vacation. I’d wear this for lunch outdoors, dinner, a shower, or another casual summer event where I wanted something a little nicer than an everyday sundress.

I love the green palm print against the creamy background, and the neutral touches in the print make it easy to accessorize with tan, gold, raffia, or natural textures. I tried a size 12, and it was slightly too big on me. I would size down.

That’s important with a column dress because too much extra fabric can completely change the silhouette. Instead of skimming your body, it can start hanging straight down, and suddenly you’ve become a very nicely upholstered window treatment. Lol!

The square neckline is another detail I liked. It opens up the neckline without being too low, and it gives the dress a more modern shape.

I added the Raffy Grab Bag with Leather Trim, and the natural texture worked beautifully with the tropical print.

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