Old Money Weekend Outfits You Need in Your Wardrobe

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Old money weekend outfits give you a timeless and elegant appearance, elevating your sophistication even on your off hours. Based on tailoring that has stood the test of time and using high-quality fabrics, these styles prioritize durability and versatility. As a result, the pieces remain fashionable for decades. 

When you put on old money outfits, they give you a refined look that understates your inner class and confidence. Unlike fads that go in and out of fashion, they don’t rely on flashy trends or brand logos. Instead, they use evergreen pieces to create a timeless ensemble and make a lasting, positive impression on your friends, coworkers, or even strangers!

Not sure what pieces to get? Take a look at the brand new Ann Taylor Weekend Collection!

Pieces for Old Money Weekend Outfits

Striped Knit Boatneck Midi Dress

Striped Knit Boatneck Midi Dress - old money weekend outfits
Ann Taylor

A well-built dress often serves as the base of old money outfits for women. After all, you can pair them with a jacket or choose to wear them alone!

To keep in style with the old money look, opt for dresses in neutral, solid colors or featuring very simple designs. For example, the Striped Knit Boatneck Midi Dress is black with white stripes. In addition, the short sleeves and the tie around the center add structure to the outfit, making it a perfect staple for your wardrobe.

Cropped Polo Shirt

Cropped Polo Shirt - old money weekend outfits
Ann Taylor

Polos have been a staple of old money families for a long time. So, if you want to emulate that style, you’ll want to put a polo or two in your arsenal. As always, you’ll want to choose something with a simple pattern, such as this Cropped Polo Shirt, which has a classic polo structure and strong, black and blue stripes. The collar is white, adding an understated yet dynamic aspect to the outfit.

The Seamed Barrel Ankle Pant

The Seamed Barrel Ankle Pant - old money weekend outfits
Ann Taylor

Once you have your polo shirts, you’ll need a well-constructed set of pants to really set your old money weekend outfits apart. The Seamed Barrel Ankle Pant can be worn for all your weekend adventures, but they also wouldn’t look out of place in the office. The barrel leg shape provides you with plenty of room to move around, and they taper slightly at the end for a slight yet more dynamic look. 

Denim Midi Skirt

Denim Midi Skirt - old money weekend outfits
Ann Taylor

Do you prefer the look of a two-piece outfit rather than a dress? If so, you don’t need to give up wearing a comfortable skirt to create old money weekend outfits. Denim remains perpetually in style and instantly dresses down your other old money pieces to make them the perfect, casual ensemble. 

So, you’ll want to wear this Denim Midi Skirt time and time again. Hitting at mid-calf, with a slit that goes to about the knee, the skirt provides you with room for movement, making it an excellent choice for your weekend outfits.

Denim Sweater Jacket

Denim Sweater Jacket - old money weekend outfits
Ann Taylor

Even though spring is right around the corner, you still might encounter some chilly days. So, on those colder weekends, throw on a jacket that combines common, high-quality materials, such as this Denim Sweater Jacket.

Comprised of mostly sweater material, the sweater has a button-up closure lined with denim. As a result, it’s an eye-catching piece without compromising its old money style.

Suede Boat Shoes

Suede Boat Shoes - old money weekend outfits
Ann Taylor

Good old money weekend outfits maintain the timeless, structured look from head to toe. But that doesn’t mean you need to squeeze your feet into uncomfortable shoes or teeter on high heels to achieve your fashion goals.

Instead, opt for something simple yet statement-worthy, such as these Suede Boat Shoes from Ann Taylor. Crafted of exquisite leather, they provide the right amount of grip and comfort while matching most of your outfits.

Enjoy Your Weekend!

With these old money weekend outfit options, you have the opportunity to enjoy casual, leisurely days while still looking sharp. And if you work on the weekend, these pieces won’t look amiss in most offices! Learn more about professional styles here!

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