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Dakota Chappy: A North Dakota Original

Updated: Apr 28, 2021

Dakota Chappy is the undisputed queen of prairie glam. North Dakota fashion designer Chappy Windsor presides over a fashion empire that is equal parts extra and empowering. Her boutiques, located in Minot and Bismarck, are an eclectic mix of boho, western, rocker and romantic influences.

And Chappy herself is on a mission to help women of all sizes look fabulous by providing streamlined wardrobe solutions. Her looks might seem complex, but the Dakota Chappy dressing system is all about comfort and functionality. Every item in the store is designed or chosen to help women create an easy dressing system that works for them and their busy lives.

Sunglasses and bling at Dakota Chappy

The designer, Chappy Windsor

I first met Chappy on Facebook when I stumbled upon her positively exuberant styling videos (this woman is a blonde dynamo). They’re part of an ongoing make-over series where Chappy and her staff show practical, jeans and sneakers Midwestern women how to embrace a totally different silhouette — and a different side of themselves, too.

Stepping into the store is the antidote to boring basics. Dakota Chappy is a texture lover’s dream. The racks burst with soft suede, buttery leather, and cozy cashmere. You’ll find fur and feathers, glittery earrings and ruby red lipstick.

Chappy Windsor is basically the queen of the tundra. Photo provided by Dakota Chappy

Chappy herself absolutely, proudly, a maximalist — in life, in clothing, in her boundless enthusiasm. But she dresses everyone, from the mellowest tomboys who haven’t worn a dress in years, to her fellow boho butterflies.

This store champions a complete dressing system that works because it’s built on a solid foundation of basic garments that each woman can customize. So even though the store stocks different versions of the same pieces and silhouettes, they look different depending on how they’re mixed and matched. Customers can start with a very small capsule wardrobe and build out from there.

The Dakota Chappy dressing system

Belts at Dakota Chappy

Elements of the look

The Dakota Chappy look has a few key components. The stores stock lots of dresses (including some of Chappy Windsor’s own design), as well as tights, tunics and skinny jeans. The backbone of the look is the Total Tight, an original Dakota Chappy design that combines tights and a tank into one durable, virtually fade-proof, super-comfortable garment.

It’s my favorite thing I’ve bought in the store, hands down. I live in tights and leggings all winter long and I loved my Total Tight so much I wore it out of the store. A version of this post was originally published back in 2015 and my Total Tight hasn’t been worn quite as often as the one in the photo below, but it’s probably pretty close. I’m happy to report that mine looks just as good.

In a world of fast fashion, where I’ve honestly bought garments that have fallen apart after two wears, this is a refreshing change of pace. This garment has outlasted several pairs of leggings I bought at the same time. I’d happily make the same investment again. Although by the looks of things, I won’t need to anytime soon.

A Total Tight is a Dakota Chappy Creation

The goal is smart layering, without adding bulk or fussing with hems or seams, so you’ll find lots of clever wardrobe hacks in smooth and comfortable fabrics. There are layerable sleeves called The Sleeve Solution to extend your sleeveless tops and dresses into a new season.

You’ll also find brilliant super-long tanks that don’t ride up (no matter how curvy you are), so we can all quit tugging at our camis and just get on with our lives already.

Clothing on display ranges from bohemian to cowgirl to romantic to glam. You’ll find lots of quintessentially western elements like beaded earrings and on-trend fringed leather bags. There are also some great edgy pieces like studded ankle booties that look great combined with jeans, structured jackets and delicate, hand-hewn silver jewelry.

Dakota Chappy doesn’t shy away from fur

On the other end of the spectrum, you’ll also find extravagant furs, lipstick that can last literally for days and luxurious oddities like a bison wool hat from one of the only two people to spin yarn from bison wool in the entire country. Throw in lots of floaty skirts, romantic dresses, lacy tops and plenty of layering pieces and tunics and suddenly the little shop can outfit just about anybody.

That’s totally by design.

Style for every body

Dakota Chappy stocks sizes 0-26 for a truly inclusive shopping experience. The store specializes in wide calf boots (yesssssss!) and dressing women with curves and muscles.

“That’s one of our strengths, finding something for the strong, broad-shouldered North Dakota girl who has a lot of style,” says Chappy.

A variety of shoe and boot sizes and widths are available at Dakota Chappy

Trying on clothes at Dakota Chappy is like a giant game of dress-up. Sales associates flutter by and deposit entire outfits in your dressing room. And because everybody wears the Total Tight it’s not uncommon to see staff members peeling off a layer or two spontaneously modeling outfits for customers.

I should note that I’m usually not into this kind of thing. I’m a solitary shopper and I can’t stand the idea of anybody fussing over me. But since the lines the store carries range, it’s really just more efficient to put yourself in their hands. They’re not overbearing about it and I never felt pressured.

It’s a really friendly, empowering place, the kind of shop where everybody’s laughing and chatting with the people in the next dressing room.

So whether you need an entirely new look, or want to upgrade to basics that will last forever, I’d suggest stopping by Dakota Chappy. The store’s entire goal is to make women look good and feel great while spending less time getting dressed. That’s something I can totally support.

Colorful Accessories at Dakota Chappy in Minot

What about you? What do you love about Dakota Chappy? What are your wardrobe challenges at the moment? What items are you looking for this season? What makes a shopping experience memorable for you?

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