What to Wear with a Hawaiian Shirt: A Complete Guide
The Hawaiian shirt is a focal-point piece. Whatever you pair with it determines whether the outfit reads as intentional menswear or as costume-y vacation attire. Here's the breakdown.
The core principle
The Hawaiian shirt is the bold piece. Everything else stays neutral. One bold item per outfit.
What to wear with a Hawaiian shirt: pants
Best options
- Chinos in earth tones: tan, olive, navy, charcoal. Classic.
- Dark indigo jeans: dressy enough to anchor without competing.
- Linen pants: summer-appropriate, drape similar to the rayon shirt.
- Relaxed cargos in solid colors: streetwear move.
- Black jeans: for evening or dressed-up casual.
What to avoid
- Hawaiian shorts (matching set = uniform)
- Patterned shorts of any kind
- Bright colored pants
- Tactical or cargo pants with visible hardware
- Heavily distressed jeans
What to wear with a Hawaiian shirt: shorts
- Chino shorts in solid colors: tan, navy, olive. Default.
- Denim shorts in dark or medium wash: relaxed casual.
- Solid swim trunks for beach contexts: only on the beach.
Avoid: cargo shorts, athletic shorts, anything patterned.
What to wear with a Hawaiian shirt: shoes
| Style of outfit | Best shoes |
|---|---|
| Casual summer | Canvas sneakers (Vans, Converse) |
| Dressed up | Clean leather sneakers, loafers, boat shoes |
| Streetwear | Chunky sneakers, low-top New Balance |
| Beach context | Simple slides or sandals (no socks) |
| Long-sleeve fall version | Leather sneakers, low boots |
Layering with a Hawaiian shirt
Plain tee underneath (most common)
White, navy, or grey tee under the open Hawaiian shirt. Most flexible layering option.
Cardigan or denim jacket over (cooler weather)
Hawaiian shirt buttoned + denim jacket or cardigan layered over. Subtler look.
Tucked under a button-up (rare but works)
Hawaiian shirt tucked into chinos with a denim or chambray button-up open over it.
Accessories that work
- Simple watch: leather strap or steel link, modest face.
- Tortoiseshell sunglasses: warm-toned, complements most patterns.
- Plain dad hat: solid color, no graphic.
- Simple belt: brown or black leather.
Accessories to avoid
- Lei or tropical-themed costume jewelry
- Tropical-print hats or accessories
- Loud-color watches
- Sandals with socks
The Hawaiian shirt is the painting. The rest of the outfit is the wall it hangs on. Don't paint the wall.
Outfit formula examples
Casual summer afternoon
Hawaiian shirt + plain white tee underneath + chino shorts + canvas sneakers + tortoiseshell sunglasses.
Dressed-up dinner
Hawaiian shirt (subtler print) tucked + chinos + leather sneakers + simple watch.
Streetwear move
Hawaiian shirt fully open + plain graphic tee + relaxed jeans + chunky sneakers + plain dad hat.
Cool-weather fall version
Long-sleeve Hawaiian shirt + dark jeans + leather sneakers + denim jacket layered over.
Where this fits
For more, see How to Wear a Hawaiian Shirt. For other summer styling, How to Style Graphic Tees. Browse all Hawaiian shirts.
Frequently Asked Questions
What pants go with a Hawaiian shirt?
Chinos in earth tones (tan, olive, navy, charcoal), dark indigo jeans, linen pants, relaxed cargos in solid colors, or black jeans for dressed-up looks. Avoid Hawaiian shorts, patterned shorts, bright colors, and heavily distressed jeans.
What shoes go with a Hawaiian shirt?
Canvas sneakers for casual summer. Clean leather sneakers, loafers, or boat shoes for dressed-up. Chunky sneakers for streetwear. Simple slides for beach. Avoid sandals with socks.
Can you wear shorts with a Hawaiian shirt?
Yes, but stick to solid-color chino shorts or dark/medium wash denim shorts. Avoid cargo shorts, athletic shorts, and patterned shorts.
Should you wear a tee under a Hawaiian shirt?
Yes, especially for streetwear and casual contexts. A plain white, navy, or grey tee under an open or partially buttoned Hawaiian shirt is one of the most flexible looks.
What accessories go with a Hawaiian shirt?
Simple watch on leather or steel strap, tortoiseshell sunglasses, plain dad hat in a solid color, simple leather belt. Avoid tropical-themed jewelry and loud watches.
Can you wear a Hawaiian shirt to a wedding?
Beach or destination weddings, yes — pair a subtler-print Hawaiian shirt (tucked) with linen pants and leather sandals. Traditional weddings, no — too casual unless explicitly the dress code.
What's the best way to style a Hawaiian shirt for fall?
Long-sleeve Hawaiian shirt + dark jeans or chinos + clean leather sneakers + denim or chore jacket layered over. The long-sleeve version extends the style into 50-65°F weather.
Image credits:
Hero image: Photo by Karsten Würth on Unsplash