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The modern guayabera by Y.A.Bera is having a moment - especially among younger men who want something sharp, cultural, and comfortable for summer. It’s the perfect balance of tradition and modern menswear, and when paired with shorts, it becomes a go-to look for beach trips, summer brunches, date nights, resort vacations, and outdoor weekends.
If you’ve ever wondered how to style a guayabera with shorts without looking messy or dated, this guide breaks down five modern outfit ideas that work for men in their 20s and 30s who care about fit, quality, and looking good without trying too hard.
Before talking outfits, there’s one rule that changes everything:
Fit matters more than anything else.
For shorts:
Look for a 7–9 inch inseam.
They should sit above the knee - not baggy, not oversized.
For your guayabera:
The shirt is designed to be worn untucked.
The hem should never fall lower than mid-zipper.
If it covers most of the shorts, it’s too long.
A well-fitted guayabera has the sharpness of a dress shirt with the ease of a camp collar shirt, giving you a clean, confident, and put-together look instantly.
This is your elevated summer style - the look that says I’m on vacation, but I know how to dress.
How to wear it:
Guayabera: Light color - white, sky blue, light grey, or sand beige.
Shorts: Charcoal, navy, or merlot red shorts.
Shoes: Leather loafers, driving moccasins, or espadrilles.
This outfit works for rooftop bars, resort dinners, cigars at a lounge, or anywhere you want to make an impression without wearing long pants in the heat. It embraces the luxury side of the guayabera while staying relaxed.
When you want something stylish but not too formal, try a bold color or modern embroidered detail.
How to style it:
Guayabera: Merlot red, charcoal grey, navy.
Shorts: Khaki, charcoal, or grey shorts.
Shoes: Clean white sneakers.
This look works great for casual Fridays, summer office environments, backyard parties, or a laid-back date night. It’s young, modern, and polished without looking like you tried too hard.
Denim shorts can look sharp - if done the right way. No distressing, no frayed hems, and no overly faded washes.
Wear it like this:
Shorts: Dark or mid-wash denim.
Shoes: Suede derbies or refined sneakers.
It’s an understated look perfect for brunch with friends, farmer’s markets, or exploring a new city. The guayabera elevates the denim so you look sharp without giving up comfort.
This is a huge trend with younger generations and an easy way to look sophisticated without complex styling.
How to style it:
Guayabera and shorts in the same color family:
Light gray shirt, charcoal shorts
Sand shirt, khaki shorts
Royal blue shirt, navy blue shorts
Shoes: Minimalist sandals, boat shoes, or slip-ons.
Since the colors blend, focus on texture contrast - linen against cotton, open weave against smooth twill. The simplicity makes the look modern and fashion-forward.
This is your carefree summer outfit - easy, relaxed, and perfect for maximum sun.
Wear it like this:
Guayabera: Short-sleeved version in a bright color or classic white.
Shorts: Seersucker, linen blend, or cotton blend.
Shoes: Quality flip-flops, woven sandals, or leather slides.
From the pool deck to the boardwalk, you stay cool, breathable, and effortlessly stylish - way more elevated than a tank top or T-shirt.
Do:
Choose tailored shorts with a clean leg line.
Roll the sleeves for a relaxed but intentional look.
Experiment with textures and minimal jewelry (leather bracelet, thin chain, etc.).
Stick with clean, premium footwear - your shoes elevate the whole outfit.
Don’t:
Wear cargo shorts (ever).
Let the guayabera run too long.
Go oversized for the sake of “retro” style - it never looks intentional.
Mix gym shorts with a guayabera.
The modern guayabera is a perfect warm-weather wardrobe essential for the younger generation—breathable, sharp, rooted in history, and ready for weekends, vacations, dates, and everything in between. When you get the fit right and pair it with the right shorts, it becomes a summer style superpower.
