Stüssy, the pioneer of California streetwear, has always embodied a relaxed, surf-meets-skate aesthetic.¹ Central to this vibe is the art of the perfect fit—specifically, the casually confident drape of an  Unlike brands that demand a tailored look, Stüssy invites you to embrace slouchy comfort, but achieving the ideal look requires more than just grabbing the biggest size on the rack. It’s about understanding the brand's true-to-size foundation and knowing when to size up for effect.

This comrehensive guide will unlock the Stüssy sizing secret, helping you master the nuanced world of oversized tees, boxy hoodies, and relaxed-fit trousers to curate a look that is authentically and effortlessly cool.

? The Foundation: Stüssy’s True-to-Size Baseline

Before venturing into the realm of 'oversized,' it's crucial to understand Stüssy's baseline. Generally, Stüssy clothing is designed to fit true to size (TTS), but with a foundational, naturally relaxed cut inherent to the streetwear DNA.⁴

• T-Shirts and Tees: Stüssy T-shirts often come with a slightly relaxed construction that is typically longer in the body than a traditional 'slim-fit' tee.⁵ For a comfortable, standard streetwear fit that is already relaxed, your usual size is often the best choice.⁶

   

• Hoodies and Sweatshirts: These pieces also tend to follow a relaxed-fit philosophy.⁷ Taking your normal size will give you a cosy, roomy, and comfortable feel without appearing sloppy. The cotton jersey used is often high-quality and heavyweight, which helps the garment maintain its structured, boxy shape.

   

• Jackets: Most jackets are cut TTS, but the overall silhouette often leans towards a workwear-inspired boxiness. For styles like chore jackets, your regular size will likely provide enough room for light layering, maintaining the sharp, yet relaxed, boxy shoulders.

• Bottoms (Trousers & Shorts): Stüssy bottoms are generally designed with a looser, relaxed fit around the leg.⁸ For a standard, non-tight fit, stick to your measured waist size. The length and overall bagginess will typically follow the brand's aesthetic.

   

⬆️ The Oversized Art: Sizing Up for Intentional Slouch

The true Stüssy style often involves an intentionally exaggerated, slouchy, or flowy fit. This is where sizing up comes into play. The goal is to maximize comfort and achieve a laid-back, "stole-it-from-my-older-brother" aesthetic without getting lost in the fabric.

1. The Oversized T-Shirt Strategy

For many, the oversized tee is the cornerstone of the Stüssy look.

• Go Up One Size: If you are seeking a distinctively oversized and slouchy fit—where the shoulder seam drops significantly, and the body drapes loosely—you should size up once from your TTS. For example, if you normally wear a Medium, choose a Large.

• Consider Your Build: If you have a wider build, sizing up might only achieve the standard relaxed fit. To get the slouchy effect, you may need to go up two sizes, but be cautious of the length becoming too long and turning into a dress.

• Post-Wash Shrinkage: Some older Stüssy items, especially 100% cotton tees, have been known to shrink slightly in the wash. If you plan on machine-drying and are between sizes, sizing up once is a safe bet to accommodate shrinkage while still landing a relaxed-to-oversized fit.

2. The Boxy Hoodie & Sweatshirt Maximisation

Boxy cuts are naturally wider and shorter, giving a great structure, especially when made from heavy cotton.

• One Size Up for Boxy & Slouchy: Taking one size up (e.g., L instead of M) will not only give you more room for layering but will exaggerate the inherent boxy-ness, increasing the width and drop of the shoulder for a super-relaxed, enveloping feel.

• Focus on the Shoulders and Chest: Stüssy's hoodies often have a generous chest width. Sizing up here will further emphasize a dropped shoulder look, which is key to the streetwear aesthetic. The high-quality fabrics help prevent the garment from looking shapeless.

3. Achieving the Boxy Jacket Fit

For a truly boxy and layered jacket look (think bomber, workwear, or chore jackets), sizing is essential for function and form.

• Layering Focus: If you plan to wear a thick hoodie or heavy sweater underneath your Stüssy jacket, size up once to maintain comfort and the boxy silhouette. Your TTS jacket will fit fine over a T-shirt, but adding a layer will tighten the fit and compromise the desired loose drape.

• The Box Factor: A boxy fit is about width and a defined, straight-cut torso. Sizing up enhances this width, turning the jacket into a statement outer shell.

? The Golden Rule: Always Check Garment Measurements

While the "size up once" rule is a solid secret for achieving the desired oversized aesthetic, it's not a universal law. Product page measurements are your most reliable tool.

1. Measure a Favourite Piece: Take a T-shirt, hoodie, or jacket that you already own and love the fit of. Lay it flat and measure the chest width (pit-to-pit), the front length (top of the shoulder to the hem), and the sleeve length.

2. Compare to Stüssy's Chart: Compare these measurements to the size chart on the specific Stüssy product page.

3. Prioritise Width: For an oversized/boxy look, the chest width is your most important number. Choose a Stüssy size whose chest width is a few inches wider than your ideal fitted piece.

4. Watch the Length: The main danger of sizing up too much is the garment becoming too long, especially on tees and hoodies. If the chest width for the oversized look is perfect, but the length is too long, you might be better off sticking to a different piece or managing the length by tucking it in.

? Bottoms: Loose Fit vs. Baggy Fit

The relaxed aesthetic extends to trousers and shorts, but here, the sizing strategy is different, as the fit is already loose by design.⁹

• Sticking TTS: For the brand's classic relaxed or loose-fit trousers (like workgear or chore pants), taking your true waist size (e.g., 32) is almost always recommended. They are already cut with a generous width and a looser leg. Sizing up in the waist will make them too big and difficult to cinch.

• The Baggy Exception: If you want a genuinely extra baggy, ultra-low-rise look, you might size up one waist size, but you will definitely need a belt or drawstring to hold them up. This is a preference for an exaggerated look, not for standard wear.

? Summary of the Stüssy Sizing Secret

Mastering the Stüssy fit is about honouring the brand’s history of effortless cool. By understanding that their regular fit is already relaxed and that sizing up once is the key to unlocking the true, modern oversized silhouette, you can confidently build a wardrobe that perfectly captures the spirit of the iconic label. Always measure, buy with intent, and let the clothes drape.