Woody & Jessie

Woody has been the sheriff of Andy's room since 1995, and in all that time he's never changed his outfit. Same plaid shirt, same cow-print vest, same hat that somebody's always trying to steal. Jessie joined him in Toy Story 2 in 1999, yodeling, braided and wearing chaps with more confidence than most real cowgirls. This June, Toy Story 5 hit theaters and set a franchise record for its opening weekend, which means a lot of people are about to show up at Halloween parties in cowboy boots. HalloweenCostumes.com sells both characters under its FUN Costumes label: a Disney Deluxe Toy Story Woody Costume for Men starting at $79.99 and a Deluxe Disney Toy Story Jessie Costume for Women at $79.99.

Put together, the pair costs $159.98 in regular sizes. Add Jessie's braided wig and you're close to $200, which is more than a Mr. Potato Head, less than a trip to Toy Story Land and exactly the kind of number that makes you check whether you already own cowboy boots.

The two costumes are built differently. Woody's is an eight-piece set that includes almost every accessory from the movie. Jessie's is simpler, a four-piece with a clever trick in the pants. Woody has six reviews, while Jessie's standard version has none, though the plus-size version of the same design has five. So this review covers what's in each box, how they fit and what buyers said, including one very specific complaint about Woody's pull string.

Woody comes with the whole toy box

The Woody costume (item FUN3339AD) is a very complete set. It includes eight pieces: a shirt, a vest, pants, a hat, a bandana, a belt with a buckle and holster, a badge and a pair of boot covers. Everything is 100% polyester except the bandana, which is 97% polyester and 3% cotton.

The shirt is jersey knit with a printed plaid and closes with hook-and-loop. The pants are a printed denim-weave with an elastic waistband. The vest is cowhide print with striped edging. The badge is rubber, the holster is faux leather and the hat is faux suede with a chin cord, so it stays on when you're dramatically jumping off furniture yelling "Reach for the sky."

The boot covers are the detail that makes this feel like a full costume. They go over your own shoes, so you don't need to buy cowboy boots for one night, and you still get the look. That alone saves you from buying real boots for one night. And it's officially licensed and a Made By Us exclusive.

About that pull string

Here's the detail that one buyer really noticed. Woody's vest has his famous pull string printed on it, rather than as a real cord or a sticker. And the vest fabric is thin.

Thomas, who left a five-star review in September 2026 titled "Cute, but some things are lacking," put it this way: "We loved this, but the vest is very thin making it see through. This wouldn't be a problem for costumes, but the pull string is printed on it. The pull string is super clear. A sticker instead would have been better." He still recommended it, and ended with, "Still great, a small upgrade could make this better."

So the pull string is there, just not in the form you might expect. If you want the real thing, a white cord with a plastic ring from a craft store or Amazon would take about five minutes to safety pin to the back. And if the see-through vest bothers you, a thin brown or white T-shirt under the plaid shirt helps. Woody would never tell you. He's too polite.

How Woody fits (and why the tall sizes matter)

Woody's size chart is unusually detailed, and it includes tall sizes, which you don't see often on costumes. It comes in X-Small, Small, Medium, Large and X-Large at $79.99, plus Medium Tall and Large Tall at $89.99 and X-Large Tall at $99.99.

The chest runs from 36 inches on the X-Small to 50 inches on the X-Large. In the regular sizes, the shirt length is short: 25 inches on the X-Small up to 27¼ inches on the X-Large. The tall sizes add about two inches to the shirt, with Medium Tall at 28 inches, Large Tall at 28½ and X-Large Tall at 29¼. They also add a bit to the sleeves and the vest, and they bring the inseam up to 34 inches, compared with 31 to 33 inches in the regular sizes.

The pants waist is elastic and covers a wide range: 23¾ to 33¾ inches on the X-Small, up to 37¾ to 47¾ inches on the X-Large. The belt gets longer with each size, from 30 inches to 46.

If you're around 6 feet or taller, the tall sizes are worth the extra $10 to $20. As you'll see in the reviews, short shirts are a recurring complaint.

What Woody buyers are saying

The Woody costume has six reviews and a 4.3-star average: three five-star reviews, two four-star and one three-star. They like the detail, and they're pretty consistent about the fit.

Dolores gave it five stars: "Costume comes with all the details which make this a great deal. The vest runs small if you are not super thin." Stephen, also five stars, wrote, "Great costume set. Came with a lot of detailed pieces and the screen printing of the material is great too!" Kenneth gave it four: "It's stretchy material, works good as a cute costume."

The sizing notes come from Janice and Gregory. Janice ordered a Small and gave three stars, explaining, "The costume has all the details needed to be an authentic Woody. My 3 star review is due to it running smaller (Small Adult) than the advertised size." Gregory, who's 5'10" and 175 pounds, bought a Large and gave four: "Really nice costume. I am a traditional mens size large shirt. Both the shirt and vest were a bit too small and the shirt tail was very short (hard to keep tucked in)."

That's three reviewers out of six saying something runs small, mostly the vest and shirt. So the advice is simple: size up, or go for a tall size if you're over average height. The elastic waist on the pants means sizing up won't leave you with pants falling down. And since the shirt tail is short, a tall size might save you from the "untucked cowboy" look, which is fine for a real cowboy but not for a toy who was made in a factory.

Jessie's pants do the heavy lifting

The Jessie costume (item FUN3382AD) has four pieces: a shirt, pants, a belt and a hat. The shirt is 96% polyester and 4% spandex, and the pants are 95% polyester and 5% spandex, so both have some stretch.

The trick is in the details. The shirt has a real two-button placket up top, and below it the rest of the buttons are printed on. The pants have cowhide-print chaps sewn right onto the legs, so there's no separate piece to strap on or lose in an Uber. The belt is faux leather and threads through the belt loops. The hat is faux suede with a chin cord and a plastic cord lock, which means you can pull it tight when you're doing Jessie's big "yee-haw" moment on the dance floor.

It's a smart way to make the costume look detailed without a pile of separate pieces. According to the plus-size version's listing, the printed graphics "give the simple garments the more detailed appearance of Jessie's blouse and pants."

What's not included is the hair, and Jessie without her red braid is just a woman in chaps. You'll also need boots.

How Jessie fits

The standard Jessie costume comes in X-Small through X-Large, all at $79.99. The chest runs from 33.5 inches on the X-Small to 44 inches on the X-Large. Shirt length goes from 21.75 to 24 inches, and the sleeves from 22.25 to 23.75.

The pants waist is elastic, with a big range in each size: 22 to 32 inches on the X-Small, up to 32 to 42 inches on the X-Large. The inseam is 29 inches in every size except X-Large, which gets 29.5. That's on the short side for tall women, although with boots it probably won't matter much, since Jessie's pants are tucked into hers anyway.

There's also a plus-size version (item FUN3382PL), on sale for $79.99, down from $99.99, in sizes 1X through 5X.

No Jessie reviews yet, but the plus size has some

The standard Jessie costume has no reviews. The plus-size version, which uses the same design, has five reviews and a 3.8-star average, and they're worth reading because they tell you how the pieces fit together.

People love the material. Elizabeth, who's 5'4" and bought a 3X, titled her review "GREAT costume & worth the money!" and wrote, "I have to say how pleasantly I was surprised with the quality of the material the costume is made out of. Normally when you purchase costumes, they are made out of super thin material & wear/tear pretty quickly. The quality of this costume is very nice & well worth the money." She also liked the hat, which she said "wasn't just a flimsy little hat." CRISTY, who ordered a 2X, wrote, "Extremely Comfortable, and very well made. The hat,pants and shirt, are breathable. True to size and would recommend."

But the fit between shirt and pants comes up again and again. Elizabeth said, "The pants were a little big around my waistline, but if I had ordered the next size down the shirt would have been too small." Kayla Anderson titled her review "Doesn't fit me right" and wrote simply, "I Love The Costume, but pants are too big & the shirt is small."

A buyer who ordered a 1X had the same issue, plus a problem with the belt: "I don't know if the belt was a smaller size then a 1X but I couldn't even fit the belt on." She added, "It kind mess up my whole costume but I couldn't return it because I needed a costume the next day."

So in the plus-size version, the shirt tends to run small and the pants large, and the belt may be tight. It's not guaranteed the standard sizes work the same way, but it's worth being ready. Size for the shirt, and keep a couple of safety pins handy for the pants waist. If the belt doesn't fit, a plain brown belt from your closet will look almost the same.

The braid problem

Jessie's hair is the part of the costume people recognize first. HalloweenCostumes.com sells a Women's Toy Story Jessie Wig (item EL161004) for $39.99. It's a pre-styled braided wig with a center part and a yellow bow, made with a polyester hair net and acrylic yarn, and it has a mesh cap with an elastic band. One size fits most, and like most wigs it's non-returnable once the package is opened.

It has four reviews, and they split two and two. One buyer called it "A perfect wig that greatly upgraded the costume," and another wrote, "Love it! Looks great on!" The other two are about size. One reviewer warned, "This wig will fit a child, or an adult with a tiny head," and another said it "fits my 3 year old."

That's a big spread, from "perfect" to toddler-sized. Since you can't return it after opening, check the fit carefully the moment it arrives, and if you have a larger head or a lot of hair, consider a different red wig or braid your own hair if it's long enough.

Boots, hats and other extras

Woody's boot covers mean he doesn't need real boots, but if you want them, the site sells Woody Costume Boots for $69.99 to $99.99. There's also a Premium Woody Hat for $34.99 if you want an upgrade from the one in the box.

For Jessie, the site suggests Women's Faux Leather Red Cowgirl Boots for $29.99, and a separate Toy Story Jessie Costume Hat for $29.99. Her hat is already included, so you only need the boots and the wig.

If you want to go further, Bullseye is always a good idea. The site suggests a Bullseye companion bag for Jessie, which is a fun way to carry your phone. And if you've got a third friend, a Buzz Lightyear costume turns your couple into the whole trio.

Summary

The Woody costume is a detailed eight-piece set with boot covers, a badge and a holster, and it comes in tall sizes. Buyers love the detail but say the shirt and vest run small and the vest is thin, with a printed pull string. The Jessie costume is a simpler four-piece with printed buttons and sewn-on chaps. It has no reviews in standard sizes, but the plus-size version gets praise for quality and complaints about shirt-and-pants sizing. The Jessie wig is a gamble on fit.

So, is this cowboy couple worth it?

For Toy Story fans, yes. At $159.98 for the pair, you're getting two very recognizable characters, and Woody especially comes with more pieces than most costumes do. The key is sizing: go up a size for Woody, or pick a tall size if you're taller than average, and for Jessie, size for the shirt and be ready to pin the waist.

I'll admit the printed pull string made me laugh. It's the most important part of Woody, the thing that makes him talk, and it's a picture on the back of a thin vest. But that's also an easy fix with a piece of cord and a safety pin, and it's not a reason to skip the costume.

Order early enough to swap sizes if you need to, and check the wig the day it arrives. Bring a cord for the pull string, a belt for Jessie just in case, and practice your "yee-haw." There's a snake in your boot, and everyone at the party is going to want a picture.