6 Tips for Styling Oversized Clothing Without Looking Sloppy
Oversized clothing has become a cornerstone of modern men’s fashion, offering comfort, confidence, and effortless style. From oversized blazers to relaxed trousers, this trend allows for versatility and self-expression. However, pulling off oversized looks without appearing unpolished requires strategy. The key lies in balancing proportions, choosing structured pieces, and styling with intention.
Whether you’re experimenting with oversized styles for the first time or refining your approach, these six tips will help you wear oversized clothing with elegance and confidence.
1. Balance proportions
Oversized pieces naturally draw attention, but pairing them with fitted elements creates harmony and prevents the outfit from overwhelming your frame.
How to style it: Pair an oversized blazer with slim-fit trousers or skinny jeans to create contrast. If you’re rocking an oversized t-shirt, balance it out with tapered joggers or tailored chinos for a sleek finish. The key is to highlight one oversized piece while keeping the rest of the outfit structured.
Recommended product: Kidoriman Casual Smart Blazer – A structured yet relaxed blazer that pairs effortlessly with fitted bottoms. Perfect for adding sophistication without sacrificing comfort.
2. Define your waistline
Loose silhouettes can sometimes drown your shape, so defining your waist helps add structure and keeps the look intentional.
How to style it: Use a leather belt to cinch an oversized shirt or blazer at the waist for a sharp, tailored effect. Alternatively, tuck the front of an oversized shirt into your pants to create a relaxed but polished vibe.
What to look for: Look for adjustable belts with bold buckles for added flair, or drawstring trousers that provide flexibility without sacrificing style.
Recommended product: Fossil Men’s Leather Belt – A sleek and durable option to add definition to any oversized outfit.
3. Layer with purpose
Layering oversized pieces creates depth, but it’s important to do it thoughtfully to avoid bulkiness.
How to style it: Start with slim-fit base layers like a fitted turtleneck or tank top, and then add oversized outerwear, such as a long kimono shirt or loose blazer. Stick to complementary tones and fabrics to keep the look cohesive.
Recommended product: Kidoriman Embroidered Kimono Shirt – Lightweight and versatile, perfect for layering while adding a touch of personality.
4. Focus on fabrics and textures
The type of fabric you choose can transform an oversized outfit from sloppy to sophisticated. Structured fabrics like wool and denim add definition, while softer materials create a more relaxed feel.
How to style it: Pair heavier, structured pieces like an oversized denim jacket with lighter fabrics like cotton or linen to create visual balance. Layering different textures can add interest without overwhelming the look.
What to look for: Opt for high-quality fabrics like cotton, wool, and linen for a polished and breathable feel.
Recommended product: Levi’s Men’s Trucker Jacket – A structured denim piece that adds sharpness to oversized outfits.
5. Keep accessories minimal
When wearing oversized clothing, simplicity is key. Minimal accessories help create balance without drawing attention away from the outfit.
How to style it: Pair oversized tops or blazers with subtle accessories like a leather bracelet, a sleek watch, or classic sunglasses. Avoid flashy or oversized accessories that can make the look feel cluttered.
Recommended product: Ray-Ban Aviator Sunglasses – Timeless and versatile, these shades complement any oversized look.
6. Ground the look with the right footwear
Shoes are the foundation of any outfit, and they play an even bigger role when styling oversized clothing. Footwear can elevate your outfit and ensure it feels intentional rather than accidental.
How to style it: Pair oversized jeans or joggers with sleek sneakers for a casual vibe. If you’re wearing oversized blazers or coats, opt for polished leather loafers or Chelsea boots for added sophistication.
What to look for: Neutral-colored shoes that complement multiple outfits without overpowering the look.
Recommended product: Common Projects Original Achilles Sneaker – Sleek, minimalist, and versatile—perfect for grounding oversized styles.
Styling oversized clothing is all about intentionality. By balancing proportions, layering thoughtfully, and focusing on fabrics and accessories, you can create outfits that feel stylish rather than sloppy. Whether you’re dressing up with a structured blazer or keeping it casual with an embroidered kimono shirt, these tips will help you master the oversized trend.
Focus on high-quality fabrics, versatile colors, and timeless accessories to elevate your look. Don’t forget to invest in the right shoes and belts to ground your outfit and add polish.
Ready to redefine oversized fashion? Start exploring pieces like the Kidoriman Casual Smart Blazer and Embroidered Kimono Shirt for standout looks that balance comfort and sophistication.
