Tailored shorts are a versatile wardrobe staple that can elevate your style during the warmer months. Unlike casual, baggy shorts, tailored shorts have a more refined fit and offer a balance of comfort and elegance. Whether you’re heading to a weekend brunch, a summer wedding, or a casual day at the office, knowing how to style tailored shorts is key to a polished look. In this blog, we explore eight ways to style tailored shorts for men to help you look effortlessly stylish no matter the occasion.
1. Pair them with a crisp button-down shirt
A classic and easy way to style tailored shorts is to pair them with a crisp button-down shirt. This combination works well for events like brunch with friends or an afternoon gathering. Opt for a slim-fit or casual button-down shirt to achieve a balanced silhouette. A light-colored shirt, such as white, light blue or light gray, goes perfectly with shorts in neutral tones. For a casual touch, you can roll up the sleeves or let the shirt hang over the pants.
Tips:
Choose breathable fabrics like cotton or linen for a more relaxed look.
Pair with loafers or stylish sneakers for extra comfort.
2. Wear a light sweater or knit polo shirt
When temperatures drop slightly, wear a light sweater or knit polo shirt over your tailored shorts. A knit polo made from fabrics like cotton or merino wool adds a touch of elegance without looking too formal. On cooler days, a finely knitted sweater in neutral tones can keep you warm while maintaining a smart look. This combination works well for a smart casual look, whether you’re attending an outdoor event or enjoying dinner at a rooftop bar.
Tips:
Stick to colors like navy, beige or olive to keep it sophisticated.
A belt can help accentuate your waist and elevate the overall look.
3. Opt for a smart casual look with a blazer
For a more elevated look, pair your tailored shorts with a blazer. This smart casual look combination is perfect for occasions like garden parties or an afternoon wedding. A lightweight blazer, such as one made of linen or cotton, will complement the relaxed appeal of the shorts while keeping the look chic. Opt for a tailored blazer that sits well on the shoulders and chest and ensures that the overall outfit remains structured.
Tips:
A blazer in a neutral shade like navy or gray will go well with most shorts.
Pair it with loafers or leather sneakers to dress up the look.
4. Casual look with t-shirt and sneakers
For a relaxed day, there’s no better combination than tailored shorts and a classic t-shirt. A quality, fitted t-shirt creates a clean and casual look that’s great for weekends or casual outings. Stick to neutral tones like white, grey or black for a timeless style, or opt for a printed t-shirt to add a touch of personality. Pair your ensemble with white or black sneakers for a fresh and comfortable finish.
Tips:
Make sure the t-shirt fits well – neither too tight nor too loose.
Add accessories like a watch or sunglasses for some extra flair.
5. Sporty vibes with a bomber jacket
If you’re going for a sporty yet stylish look, a bomber jacket with tailored shorts is a great option. The bomber jacket adds a cool twist to the smart look of the shorts, making it perfect for casual events or a relaxed night out. Stick to neutral colors for the jacket, like black or olive, to avoid clashing with the shorts. Pair it with a simple t-shirt or polo shirt underneath for added comfort and style.
Tips:
Sneakers are your best footwear choice for this sporty vibe.
Don’t overdo it with accessories – keep it simple with a clean look.
6. Wear a casual button-down shirt over a t-shirt
For a casual yet polished look, you can wear a casual button-down shirt over a plain t-shirt. This combination allows you to keep the outfit casual while still showing a touch of effort. Roll up the sleeves of the button-down shirt for a more casual look and let the hem of the t-shirt peek out for an extra detail. This look is perfect for beach outings, casual dinners, or a day at the park.
Tips:
Choose a shirt made of a lightweight fabric like linen or cotton.
Pair it with sandals, boat shoes, or casual sneakers.
7. Pair it with stylish loafers for a dressy look
For occasions that call for something more dressy, consider pairing your tailored shorts with stylish loafers. This combination works well for summer parties, business casual occasions, or even a night out on the town. The loafers add a sophisticated touch, while the tailored shorts keep the overall look fresh and modern. Opt for loafers in classic colors like brown, navy, or black, depending on the color scheme of your outfit.
Tips:
Make sure your tailored shorts are hemmed to the right length—just above the knee—so proportions are optimal with loafers.
A stylish belt can help complete the look.
8. Stay relaxed with a Hawaiian shirt
For a more fun, tropical vibe, pair your tailored shorts with a Hawaiian shirt. This relaxed and colorful look is ideal for vacation or a day out on a warm summer afternoon. Hawaiian shirts come in a variety of prints, so you can choose one that suits your personal style. To add a little more elegance to the outfit, choose a fitted Hawaiian shirt and avoid cuts that are too baggy. The tailored shorts will balance out the loose-fitting top and add a chic contrast.
Tips:
Stick to a color palette that complements the shorts – avoid clashing prints.
Pair it with flip-flops or casual loafers for a beach-ready look.
Key Tips for Styling Tailored Shorts
Fit is important: When choosing tailored shorts, make sure they fit well around the waist and hips. They should neither be too tight nor too loose. For a flattering look, the length should end just above the knee.
Fabric Choice: Fabrics like cotton, linen or wool blends are excellent options for tailored shorts as they are breathable and comfortable, making them perfect for warmer weather.
Balanced Proportions: If your shorts are on the looser and looser side, balance the outfit with a more form-fitting top. On the other hand, if you’re wearing a loose shirt, opt for slimmer shorts for a balanced look.
Accessories: Don’t forget to wear accessories! A well-chosen watch, sunglasses or belt can take your outfit to the next level.
Footwear: Your choice of footwear can completely change the appeal of the look. Sneakers, loafers, boat shoes and even sandals pair well with tailored shorts depending on the occasion.
Conclusion
Tailored shorts are a versatile piece of clothing that is a must-have in any man’s summer wardrobe. With a few simple styling tricks, you can create looks that range from casual to smart-casual, so you’re ready for any occasion. Whether you’re heading to the beach, going to a dinner party or just running errands, tailored shorts offer comfort, style and elegance all at the same time. Experiment with different combinations and find what works best for your personal style – you’ll be amazed at how versatile this essential piece of clothing really is!
