How to Style Oversized Shirts Without Looking Sloppy

Oversized shirts are a major fashion trend in 2025, and for good reason—they’re comfortable, stylish, and versatile. However, pulling off the oversized look without appearing sloppy can be tricky. The key lies in smart styling, balanced proportions, and the right accessories. In this article, we’ll show you how to style oversized shirts with intention while incorporating timeless fashion elements like Guidi Boots, men’s designer boots, and handmade boots to elevate your entire look.

1. Balance the Volume with Slim-Fit Bottoms

When wearing an oversized shirt, the first rule is balance. Pairing a loose top with skinny jeans, fitted trousers, or leggings helps create a flattering silhouette. For women, pairing an oversized white shirt with black faux leather leggings can make the look chic. For men, slim-fit denim with a crisp oversized Oxford shirt is a go-to combo.

Complete the look with men’s designer boots for a clean and structured touch. These boots ground the outfit and add a polished edge.

2. Tuck It In (Or Half-Tuck) for a Tailored Effect

One of the easiest ways to avoid a sloppy look is to tuck in your oversized shirt. Whether it’s a full tuck into high-waisted trousers or a casual half-tuck with jeans, this styling trick instantly adds shape and intention to your outfit.

A tucked oversized shirt looks amazing when paired with Guidi Boots, which bring luxury, character, and an artisanal flair to your ensemble.

3. Add a Belt to Define Your Waist

Belting an oversized shirt is a smart way to add structure and create a flattering shape. Choose a wide leather belt for a bold statement or a thin fabric belt for a subtler approach. This works especially well with shirt dresses or tunic-length shirts.

Ladies can pair belted shirts with boots or heels, while men can explore belted shirt jackets with handmade boots for a rugged yet stylish outfit.

4. Layer with Structured Pieces

Wearing an oversized shirt under a structured jacket, blazer, or coat adds refinement to your look. The contrast between a boxy shirt and a tailored outer layer creates a harmonious balance between relaxed and formal.

Layered looks work well with accessories like luxury boots. Try wearing men’s designer boots with dark jeans, an oversized shirt, and a trench coat for a refined, layered outfit.

5. Play with Proportions for a Fashion-Forward Look

Fashion-forward styling often involves playing with proportions. Combine an oversized shirt with wide-leg trousers or longline coats for a high-fashion streetwear vibe. The key is to commit to the exaggerated proportions while balancing textures and colors.

For example, a flowy white oversized shirt with loose khaki pants and black Guidi Boots creates an artistic, editorial-worthy ensemble.

6. Accessorize Strategically

Accessories can take your oversized shirt from “lazy” to “luxury.” Think crossbody bags, statement necklaces, sunglasses, or a structured hat. These finishing touches show that the look is intentional.

For men, try a leather messenger bag, vintage watch, and handmade boots for a rugged-yet-refined look. For women, bold earrings and sleek boots elevate even the simplest oversized shirt outfit.

7. Choose High-Quality Fabrics

The fabric of your oversized shirt makes a big difference. Crisp cotton, breathable linen, and soft flannel all hold shape better than thin, clingy fabrics that may sag or wrinkle. A well-made shirt instantly elevates the entire outfit.

Pairing these premium shirts with handmade boots enhances the quality of the overall look. When your pieces are made with care, your outfit automatically looks more polished.

8. Go Monochrome for Effortless Chic

A monochrome outfit is a great way to make oversized shirts look intentional and elegant. Whether you opt for all-black, all-white, or earth tones, monochrome outfits give a sense of unity and purpose.

Pair a beige oversized shirt with matching pants and tan Guidi Boots for an effortlessly cool neutral look. Men can try navy-on-navy with designer boots in a complementary shade.

9. Wear It as a Dress

An oversized shirt can easily double as a shirt dress. This is especially trendy for women. Just make sure the length is appropriate, and pair it with shorts or biker shorts underneath for added comfort.

Add a belt or a crossbody bag, and complete the look with handmade boots to give it an edgy, street-style touch. For colder days, layer with tights and a long coat.

10. Elevate with Footwear – Boots Make the Look

Your shoes can make or break an outfit—especially with oversized shirts. This is where Guidi Boots, men’s designer boots, and handmade boots come into play.

These boots are not only stylish but also provide structure and substance to your outfit. The rich textures, strong shapes, and superior materials give the overall look a refined finish. Whether it’s a bold combat boot or a minimalist Chelsea style, the right footwear adds confidence and class.

Final Thoughts: From Relaxed to Refined

Styling oversized shirts doesn’t mean sacrificing style for comfort. With the right combinations, accessories, and footwear—like Guidi Boots or handmade boots—you can transform a basic oversized shirt into a fashion-forward outfit that turns heads.

Whether you’re aiming for street style or elegant minimalism, the oversized shirt is your versatile companion in 2025. Just remember: balance proportions, keep quality in focus, and never underestimate the power of a good pair of boots.