Now in Style: 10 Best Midwest Fashion Trends Everyone’s Talking About

Midwest fashion is quietly having its moment and it’s way more fun than anyone gives it credit for. In this first part of our “Now in Style” series, we’re talking ten trends that are everywhere right now. From cozy knits and flowing maxi skirts to whimsical florals, we’re covering it all. These are the pieces that make getting dressed feel exciting again.

Maxi Skirts & Dresses

Maxi skirts and dresses are taking over the Midwest right now, and it’s easy to see why. Flowy, bohemian-inspired pieces feel effortless and airy. Meanwhile, structured column silhouettes give a polished, modern edge. No matter what you pick, these pieces are all about versatility. They work for weekend brunches, casual office days, or even a spontaneous evening out. 

Sheer & Transparent Layers

Sheer and transparent fabrics can help you make a statement! These pieces are perfect for adding dimension and interest without weighing down an outfit. A transparent top, skirt, or jacket can transform a simple ensemble into an ethereal, layered look.

Oversized Blazers & Suiting

Oversized blazers and suiting are basically the ultimate “I’ve got this” energy in clothing form. Power dressing is all about pieces that feel effortless while still making a statement. Think roomy blazers, wide-leg trousers, and tailored sets. Layer over a tee for a casual vibe, or go full-on polished with a crisp blouse. Basically, if you want an outfit that says “I run my life, my schedule, and probably three book clubs simultaneously,” oversized suiting is your new best friend.

Cargo Pants & Utility Wear

Cargo pants and utility wear allow you to mix functionality and fashion. They give off that effortlessly edgy vibe, like you’re ready for anything the day throws at you. Pair them with sneakers and a cropped top for casual chic, or throw on a blazer to give them a little polished twist. Either way, these pieces are proof that comfort and utility can be totally stylish.

Chunky Knitwear

Chunky knitwear is basically the equivalent of wrapping yourself in a warm hug — but make it fashion ✨ Oversized sweaters and cardigans that lean into bold colors, playful textures, and cozy shapes are both effortless and make a statement. Layer them over a midi skirt, tuck them into high-waisted jeans, or just let them drape over your leggings for maximum comfort-meets-style vibes.

Drop-Waist Dresses

Drop-waist dresses are quietly taking over and they’re giving all the nostalgic vibes in the best way. This silhouette is a nod to the ‘90s and early 2000s. It’s the kind of dress you can wear with chunky sneakers for a casual day out or dress it up with boots and layered jewelry for a night that feels a little more polished. 

Feminine Balletcore Aesthetic

Balletcore is the softest, dreamiest trend you didn’t know you needed. Think delicate skirts that swirl when you walk, wrap tops that feel effortlessly romantic, classic ballet flats, and yes — leg warmers because cozy and cute will never go out of style. 

Leather & Faux Leather Pieces

From sharp, structured leather blazers to bold, colored leather pants, this trend is all about edgy sophistication that feels modern and wearable. It’s the kind of style that instantly elevates an outfit. Pair a leather jacket with jeans and a tee for casual cool, or go full statement with a monochrome leather look that says, “I’m here, I’m confident, and yes, I own this vibe.”

Denim Maxi Skirts

Denim maxi skirts are giving all the best Y2K vibes but with a modern twist. These skirts work perfectly with fitted tops for a sleek, put-together look or with oversized knits when you want that cozy, effortless energy. They’re versatile, easy to style, and somehow manage to feel both nostalgic and completely fresh at the same time.

Rosettes & 3D Florals

Rosettes and 3D florals are giving outfits that extra touch of drama and whimsy this season. From dresses and tops to accessories, bold floral embellishments are popping up everywhere. They add texture, dimension, and just a hint of playful elegance. 

Get the Hottest Midwest Fashion at Sunny & Olive

If you’re looking for high-quality Midwest fashion on a budget, turn to Sunny & Olive. Since 2023, we’ve been serving the Milton, Wisconsin area with go-to consignment styles. At our store, you’ll find trendy, affordable, and quality secondhand finds. We’re all about size inclusivity and making space for everyone. And, we’re 100% women-owned and run, and all the small businesses we feature in-store are women-owned, too. From chic clothing to handmade jewelry, stickers, scrunchies, candles, soaps, and more, you’ll find plenty of treasures here. Learn more about our shop on our about page and stop in soon!