As the mercury rises and summer beckons, men’s wardrobes undergo a seasonal transformation. Shorts, once assigned to casual weekends and beach outings, have evolved into a versatile staple that can be styled for various occasions.
However, the art of pairing shorts goes beyond simply throwing on a t-shirt and calling it a day. With the right combinations, you can raise your warm-weather style to new heights, striking the perfect balance between comfort and fashion.
In this article, we’ll explore innovative and stylish ways to pair men’s shorts.
Whether you’re aiming for a polished look for a summer office, a laid-back ensemble for a beach day, or something in between, these pairings will help you navigate the season with confidence and flair. From classic combinations to unexpected twists, we’ll cover a range of styles to suit different tastes and occasions.
So, let’s dive into the world of men’s shorts and discover how to make the most of this summer essential.
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1. The Timeless Polo Perfection
Elevate your everyday look by pairing flat-front khaki shorts with a crisp, colorful polo shirt. Opt for a contrast – think navy shorts with a coral polo or khaki shorts with a deep green top.
Where to wear: Golf outings, casual Fridays, or weekend brunches.
Accessorize with: A braided leather belt, boat shoes, and a classic watch.
Pro tip: Roll the sleeves of your polo slightly for a more relaxed vibe.
2. Button-Down Brilliance
Take your shorts game up a notch by pairing tailored chino shorts with a light cotton button-down shirt. Roll up those sleeves and leave the shirt untucked for a relaxed yet refined look.
Where to wear: Outdoor dinner parties, art gallery openings, or upscale beach bars.
Accessorize with: Leather loafers (no socks!), a minimalist watch, and perhaps a pocket square for extra flair.
Pro tip: Experiment with patterns – a subtle gingham or stripe can add interest without overwhelming.
3. Linen Luxe
Embrace the full summer spirit with a matching linen shorts and shirt combo. Go for earthy tones like olive, sand, or soft blue for a sophisticated palette.
Where to wear: Beach weddings, resort dinners, or any event where you want to look put-together yet feel like you’re wrapped in a cloud.
Accessorize with: Woven leather sandals, a straw fedora, and some wooden beaded bracelets for a bohemian touch.
Pro tip: Don’t stress about the wrinkles – they’re part of linen’s charm!
4. Graphic Charm
For a youthful, edgy vibe, pair distressed denim shorts with a vintage-inspired graphic tee. Look for tees with retro band logos, classic movie posters, or quirky illustrations.
Where to wear: Music festivals, casual hangouts with friends, or a day of urban exploration.
Accessorize with: High-top sneakers, a leather cuff bracelet, and maybe a pair of round sunglasses for that John Lennon flair.
Pro tip: Keep the shorts a bit longer for this look – think just above the knee to balance the casual vibe of the tee.
5. Blazer and Shorts: The New Power Couple
Break the rules by pairing tailored Bermuda shorts with a crisp dress shirt and an unstructured blazer. Stick to a monochrome palette for a sleek, modern look.
Where to wear: Creative offices, summer networking events, or upscale rooftop bars.
Accessorize with: Suede loafers, a pocket square, and a sleek portfolio or tablet case.
Pro tip: Ensure your shorts are well-pressed and hit just above the knee for the right balance of professional and seasonal.
6. Beachwear Elevated
Upgrade your beach style by pairing patterned board shorts with a solid, slim-fit tank top or a breezy linen button-up worn open.
Where to wear: Beach days that turn into boardwalk strolls and seaside dinners.
Accessorize with: Waterproof watch, polarized sunglasses, and flip-flops that can easily be swapped for espadrilles.
Pro tip: Choose board shorts with a smaller, more subtle print to keep the look mature and versatile.
7. Henley Harmony
Pair textured cargo shorts with a fitted henley shirt for a rugged yet refined aesthetic. Opt for earth tones to enhance the outdoorsy vibe.
Where to wear: Weekend hikes that end at a microbrewery, farmers markets, or casual outdoor concerts.
Accessorize with: Leather boots, a canvas and leather backpack, and a rugged chronograph watch.
Pro tip: Roll the sleeves of your henley slightly for added texture and to show off your forearms.
8. Nautical but Nice
Channel your inner sailor by combining navy tailored shorts with a classic Breton striped top. The key is to keep the stripes thin and the fit snug.
Where to wear: Yacht clubs, seaside restaurants, or anywhere you want to feel like you’ve just stepped off a luxury liner.
Accessorize with: White canvas sneakers, a braided rope bracelet, and classic aviator sunglasses.
Pro tip: Add a pop of red – like a belt or watch strap – to really lean into the nautical theme.
9. Denim Dreams
Throw a light-wash denim jacket over a plain white tee and pair with burgundy or forest green shorts for a look that transitions seamlessly from day to night.
Where to wear: Outdoor movie screenings, bonfires on the beach, or casual dinner dates.
Accessorize with: Desert boots, a leather wrap bracelet, and a beanie for when the temperature drops.
Pro tip: Cuff your shorts once or twice for a more deliberate, styled look.
10. Retro Resort Wear
Channel 1950s Palm Springs with a Cuban collar shirt featuring a subtle print, paired with solid, high-waisted shorts.
Where to wear: Poolside parties, retro-themed events, or sipping cocktails at a tiki bar.
Accessorize with: Penny loafers, a vintage-inspired watch, and perhaps a pair of classic Wayfarers.
Pro tip: Tuck in the shirt and add a thin belt to really nail that mid-century silhouette.
11. Knitwear Know-How
For those cooler summer evenings, pair your shorts with a lightweight merino wool sweater or cardigan. The contrast of cozy top and bare legs is unexpectedly chic.
Where to wear: Sunset beach walks, outdoor cinema evenings, or al fresco dining when there’s a chill in the air.
Accessorize with: Suede chukka boots, a woven leather belt, and a simple pendant necklace.
Pro tip: Choose a sweater with some texture – like cable knit – to add visual interest to the outfit.
12. Athleisure Ace
Combine performance shorts in a solid, dark color with a technical fabric polo or a fitted, moisture-wicking tee for a look that goes from gym to street seamlessly.
Where to wear: Morning coffee runs, casual meetups, or any time you want to look put-together while staying ready for impromptu activity.
Accessorize with: High-end running shoes, a smart fitness watch, and a sleek water bottle.
Pro tip: Look for shorts with hidden pockets to maintain a streamlined look while keeping your essentials secure.
13. Print Mastery
Make a statement by pairing solid-colored shorts with a bold printed camp collar shirt. Think tropical florals, abstract geometrics, or even quirky conversational prints.
Where to wear: Summer parties, vacation sightseeing, or anywhere you want to stand out from the crowd.
Accessorize with: Simple leather sandals, a solid color baseball cap, and a few understated rings.
Pro tip: Keep the shorts and other accessories neutral to let the printed shirt take center stage.
Experiment with different combinations, find what works for your body type and personal style, and don’t be afraid to inject your own personality into each outfit. With these versatile pairings in your style arsenal, you’re ready to take on summer with panache, turning every outing into your personal runway.
So go ahead, show off those legs and let your summer style shine!