How to Style Men's Overall Shorts in 2025

Once a staple of workwear and 90s fashion, overall shorts are making a major comeback in men's style. Far from their utilitarian roots, today's designs are more tailored, stylish, and incredibly versatile. Whether you're hitting a summer festival, enjoying a casual weekend, or just want to switch up your everyday look, overall shorts offer a unique and comfortable option. This guide will walk you through how to wear them without looking like you've stepped out of a time machine.

The Modern Appeal of Overall Shorts

The resurgence of this trend is all about modern interpretation. Forget the baggy, shapeless styles of the past. The 2025 version is about a better fit and smarter styling. Brands are offering overall shorts in a variety of materials, from classic denim to lightweight linen and durable canvas. The key is finding a pair that fits well—not too tight, but not overly loose. A streamlined silhouette is crucial for pulling off this look successfully and making it feel contemporary.

Finding Your Perfect Fit

When shopping for overall shorts, pay close attention to the cut. The bib should sit comfortably on your chest, and the straps should be adjustable for a custom fit. The shorts portion should hit just above the knee for a modern look, similar to how you'd choose a standard pair of shorts. A slim or straight-leg cut is generally more flattering than a wide or baggy one. Trying on a few different styles will help you find the one that best suits your body type and personal style.

Styling Overall Shorts for Any Occasion

The beauty of overall shorts lies in their versatility. What you wear underneath completely changes the vibe. You can easily dress them up or down depending on the occasion. For an effortless, laid-back look, a simple t-shirt or tank top is a perfect choice. This classic combination is ideal for warm weather and casual outings. Sticking to neutral colors like white, black, or grey for your base layer allows the overalls to be the statement piece.

Casual and Cool

For a classic summer outfit, pair your denim overall shorts with a crisp white t-shirt and your favorite sneakers. This look is timeless, comfortable, and effortlessly cool. You can leave one strap undone for a more relaxed, devil-may-care attitude. Accessorize with a baseball cap and sunglasses to complete the ensemble. According to style experts at GQ, keeping the base layers simple is key to mastering this trend.

Elevated Streetwear

To give your overall shorts a streetwear edge, try layering them over a graphic tee or a lightweight hoodie. A bold print or logo can add a pop of personality to your outfit. Pair this with chunky sneakers and a beanie or bucket hat for a look that’s right on trend. This approach allows for more creativity and personal expression, turning a simple garment into a fashion-forward statement. Finding the perfect pair of men's overall shorts is the first step to building these stylish outfits.

Budgeting for Your New Wardrobe

Updating your wardrobe with trendy pieces can be exciting, but it's also important to manage your spending. Creating a budget for fashion helps you prioritize purchases and avoid overspending. Start by setting aside a specific amount each month for clothing. This allows you to invest in key pieces without feeling guilty. Financial planning tools and resources, like those offered by the Consumer Financial Protection Bureau, can provide valuable insights into managing your money effectively.

Sometimes, an unexpected expense can throw your budget off track right when you want to refresh your style. If you find yourself a little short before your next paycheck but don't want to miss out on a great find, exploring modern financial tools can be helpful. For instance, the Gerald Cash Advance app offers a way to get a small advance without the fees, interest, or credit checks associated with traditional options. This can help you bridge the gap and stay on top of your style game without compromising your financial wellness.