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1 Ugly Sweater Vest, 6 Cute Outfits

I found my vest—soon to become a treasured wardrobe staple—at the Brimfield Flea Market two years ago, under a giant white tent filled with vintage gems. The white tent at Brimfield is known for having the best of the best small business vintage shops from the East Coast. Talking to the women who own the shops, you will soon learn that their best finds are always from estate sales. These women are always down for the adventure and are real life treasure hunters. 

As for my vest: I immediately was drawn to it for its distinctive campy design and colors. For the first few years I’ve had this vest, I may have thought it depicted a golf scene, when in fact it is actually tennis. 

The vest tends to receive a variety of feedback every time I wear it. A man on Hinge asked me why I was wearing an ugly Christmas sweater in the summer (Automatic Unmatch, thank you, SEE YA). Another man on the street stopped me to take a picture of the vest so he could buy one like it (he cut off my face in the photo).

Because this vest is so much better than the average vest—so much more complicated, so much more demanding—I’ve found it difficult to style. Below are six looks, which I hope will inspire you to fearlessly mix and match articles of clothing you normally wouldn’t throw together. There are hundreds of outfits, even in the smallest wardrobe. Please enjoy this ugly TENNIS vest, styled six different ways. I hope you find them as cute as I do. 

1. The Casual “I Can Glide Towards You” Look 


Skating has become one of the most fun elements of my pandemic summer and, not to brag, but I suck. My dad used to rock these skates in the 8th grade and I have borrowed them from his memory chest without ever returning them. I tied my vintage vest at the bottom to create a shorter top that meets the start of my high rise Levi’s jeans (P.S. these bad boys are on sale rn). For sunnies, I am always attracted to large grandma lenses. These pink ones allow me to skate and see pink… a win win. 

2. The Picnic Lounge Outfit


This outfit has become my go-to look when meeting friends in the park. The white shorts don’t show butt sweat (key element) and they are light and airy. I decided to only button the vest twice, which shows off more of the shorts. I paired the outfit with some vintage black cowgirl boots which you can’t see (sorry)(but they’re really cute). 

3. The Any Time Any Wear Get Up


This outfit is 100% thrifted (minus the socks)! I love this look because it is both dressy and casual at the same time. It’s perfect for a day where you’re confused about whether it’s hot or cold outside. I styled it with some white socks, black loafers, and an awkward thumbs up. 

4. The Grandpa Technique


I thrifted this blue workout suit for $10 and it may be one of my best thrift finds ever. I added some green New Balance sneakers to balance out the green from the vest. Overall this is a 10/10 grandpa look. I’m ready to retire.

5. The Confused Bundled Up Fisherman 


According to the laws of the universe, when you wear a yellow raincoat you become a fisherman. It is something everyone must deal with. If you’re down for the adventure, you could embrace it and rent a boat, set sail, and never look back. I decided to add my vest on top of the raincoat to give it a revere-layered look. I’m wearing a Patagonia fleece underneath and some navy Levi’s cords. For a fun touch, I also added this blue puff bag and a hat from the Park’s Project

6. Blazer it UP


Here I paired the vest with an oversized colorful blazer, a short skirt and some boots. This could be extremely cute for a lunch date, if and when those become a thing again. Yes, this blazer has shoulder pads in it and yes I like that about it! This outfit is also 100% thrifted. If you’re wearing a vest that is longer than mine, I’m sure you could get away with making it look like a dress, which is what I hoped mine would do here (it didn’t). 

I’m sure you have a wacky piece of clothing that you bought on a limb that sits in the back of your closet, waiting for discovery and an award winning presentation. I’m sure whatever it is is looking a lot like this right now:


We literally peed our pants making this video #fyp #greysanatomy #pickme #chooseme #loveme #CheckMeOutChallenge

♬ So Pick Me – x_dallas_x

 Your fun clothing is asking you to take it for a walk so it can breathe the fresh air, pick the roses, and wear it with other pieces of clothing so it can feel cherished and loved. 

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