👔 12 Button Up Shirt Men Outfits

Button-ups aren’t just for meetings and awkward family dinners. They’re the Swiss Army knife of your closet. Dress them up, dress them down, flirt with pattern—then act like it was effortless. Let’s make your shirts do more than hang on a chair.

1. Crisp White Shirt with Dark Denim

Clean, classic, can’t miss. A slim white button-up with dark indigo jeans is your instant upgrade.

• Roll the sleeves to mid-forearm for casual confidence.
• Tuck or half-tuck depending on mood.
• Finish with white sneakers or brown loafers.

Pro tip: Go for an Oxford cloth if you want a bit more texture and structure.

It works because it’s timeless, flattering, and ridiculously easy to pull off.

2. Blue Oxford with Chinos

Prep, but make it modern. A light blue OCBD and khaki chinos balance polish and ease.

• Choose slim-straight chinos with no break.
• Add a brown leather belt to tie it together.
• Swap sneakers for desert boots when you want grown-up vibes.

Pro tip: Unbutton the second button and toss on a webbed belt for casual days.

Reliable and versatile, this combo earns compliments without trying.

3. Striped Button-Up with Tailored Shorts

Smart up top, vacation below. A vertical stripe shirt with 7–8 inch shorts keeps you sharp in heat.

• Stick to navy or olive shorts for easy pairing.
• Choose espadrilles or minimal sneakers.
• Roll the collar lightly for breezy structure.

Pro tip: Vertical stripes lengthen the torso—free height hack.

It works because it’s breezy, balanced, and still looks intentional.

4. Black Button-Up with Black Jeans

Monochrome = instant cool. A black shirt and black denim hits sleek without trying too hard.

• Pick matte fabrics to avoid nightclub glare.
• Add Chelsea boots or chunky derbies.
• Consider a silver watch for contrast.

Pro tip: Slightly looser shirt balances skinny or slim jeans.

It works because monochrome sharpens lines and simplifies style choices.

5. Plaid Flannel Over Tee with Jeans

Casual legend status. A soft plaid button-up layered over a clean tee is weekend gold.

• Keep the tee white, grey, or black.
• Go straight-leg jeans for a relaxed silhouette.
• Finish with work boots or retro runners.

Pro tip: Size the flannel slightly oversized for that effortless drape.

It works because it’s cozy, layered, and just the right amount of rugged.

6. Linen Button-Up with Linen Trousers

Light, airy, unbothered. A linen shirt with linen or linen-blend pants screams vacation mode.

• Stick to neutrals like sand, white, or sage.
• Go loafers or leather sandals depending on formality.
• Embrace the wrinkles—it’s the charm.

Pro tip: A camp collar keeps it breezy and modern.

It works because airflow meets polish, and you look cool under pressure.

7. Button-Up Under a Crewneck Sweater

Layer like you mean it. A crisp shirt peeking under a knit adds instant depth.

• Let the collar and hem show slightly.
• Pair with wool trousers or dark denim.
• Choose neutral sweaters for versatility.

Pro tip: A micro-check shirt adds subtle pattern without shouting.

It works because it layers texture and feels grown without feeling stuffy.

8. Button-Up with Suit Sans Tie

Boardroom-lite. A tailored suit with an open-collar shirt is business casual’s final form.

• Keep the shirt white or light blue.
• Go with sleek leather shoes to anchor the look.
• Fit is everything—tailor if needed.

Pro tip: A spread collar sits clean without a tie.

It works because it’s polished but relaxed, perfect for dinners and smart events.

9. Denim Shirt with Neutral Trousers

Workwear, refined. A chambray or denim shirt with beige or grey pants nails modern rugged.

• Pick a mid-wash for easier pairing.
• Try suede sneakers or brogues.
• Keep accessories minimal.

Pro tip: Cuff the sleeves to show a canvas or leather bracelet for texture.

It works because soft denim pairs effortlessly with tailored fabrics.

10. Patterned Button-Up with Dark Trousers

Let the shirt be the star. A microprint or floral with charcoal pants balances bold and clean.

• Keep patterns small-scale for sophistication.
• Neutral shoes keep the focus up top.
• Minimal jewelry, major impact.

Pro tip: Choose camp or cutaway collars to modernize prints.

It works because contrast directs attention where you want it.

11. Overshirt Button-Up with Tee and Cargo Pants

Utility, but chic. A thicker button-up as an overshirt with slim cargo pants gets things done.

• Neutral palette: olive, tan, stone.
• Pick rugged sneakers or hikers.
• Keep pockets streamlined to avoid bulk.

Pro tip: Choose twill or heavyweight cotton for structure.

It works because it’s practical and stylish—form meets function.

12. Button-Up with Knit Polo Layer

Unexpected, but slick. Wear a fine-knit polo under a relaxed button-up and leave it open.

• Go tone-on-tone like cream on beige or navy on blue.
• Pair with pleated trousers for extra finesse.
• Loafers or clean sneakers finish it right.

Pro tip: Choose a knit with a gentle collar so it lays nicely under the shirt.

It works because layered collars add dimension without bulk.

Conclusion

Button-ups aren’t boring—you just needed better plays. Mix fabrics, play with collars, dial fits, and you’ve got a week’s worth of looks from one hero piece. Keep it simple, keep it sharp, and let your shirt do the heavy lifting while you take the credit.