The shirts here run from a pleated tuxedo shirt for black tie to a plain white tee with a baseball cap, and the occasion decides which one you reach for: formal events, the office, a casual date or a hot day each point to a different shirt.
Match the shirt’s formality to everything else you wear, and the choice usually makes itself. A burgundy dress shirt tucked into black trousers is one example of how far a single color can carry an outfit.
1. Dress Shirt
A slim-fit dress shirt in a deep color like burgundy, tucked into black trousers with a belt, is a quieter choice than the usual white or light blue.
It still reads as formal, so it works for business days and events.
Keep the tuck clean and the belt matched to your shoes. Dark trousers let the shirt carry the color, so I’d skip a loud tie and let it stand alone.
2. Overshirt
Somewhere between a shirt and a jacket sits the overshirt, and a heavy fabric with a buttoned chest pocket is what makes it work as a layer. Wear it open over a plain tee instead of tucking it in.
I lean toward light, neutral shades like beige or grey because they sit easily over a white tee and nearly any pants. It saves you from reaching for a full jacket on a mild day.
3. Flannel Shirt
Plaid flannel in green and beige is the easiest version to wear, since both colors are muted and sit well with black pants. Flannel is a warm, thick shirt, so it belongs to colder weather.
Wear it buttoned as a shirt, or open over a tee when you want a looser look. Skip it in summer; the thickness that makes it useful in the cold makes it a chore in heat.
4. Cuban Collar Shirt
Open at the neck with no collar stand, a short-sleeve Cuban collar shirt sits flat and relaxed. A solid dark shade like burgundy keeps it from looking like a costume.
Pair it with black pants and sneakers, and leave it untucked.
That combination is easy, and the shirt does the work. Solids are my pick over loud patterns for everyday wear.
5. Printed Shirt
A printed shirt turns one graphic into the whole outfit, so everything else should stay plain. A cream long-sleeve button-down with a vintage car graphic and a small word on the pocket needs nothing more than black trousers.
Keep the print as the only loud thing: no patterned pants, no busy shoes. A shirt like this makes sense for casual dates and weekends, less so for the office.
6. Sleeveless T-shirts
Sleeveless tees, better known as tank tops, are for workouts and hot-weather days. A grey one with matching shorts looks put together because the tones agree.
Choose a solid color, and match it to your shorts if you want the set look.
Add sunglasses and you’re done. I’d keep them for the gym, beach and casual summer outings, not anywhere that expects a sleeve.
7. Tuxedo Shirt
A tuxedo shirt is built for black tie, and the pleated front is what separates it from an ordinary dress shirt. White with black studs and black trousers is the classic version, and it needs nothing added.
Keep the trousers plain and dark so the pleats stay the focus. I’d save this one for formal events; it looks out of place anywhere less dressed up.
8. Henley Shirt
Cream looks softer than white on a Henley, and the button placket gives a collarless shirt just enough structure to stand on its own. Dark pinstriped trousers and white sneakers make it a smart-casual outfit for a normal day.
Leave it untucked or half-tucked, and keep the top buttons undone for an easy look. If you want a shirt that sits between a tee and a button-up, this is my pick.
9. Casual Button-Down Shirt
Rust is an easy color to wear with blue jeans, since the warm shirt and cool denim balance each other. A long-sleeved button-down with a chest pocket looks best worn untucked.
Choose light blue or mid-wash jeans so the shirt stays the louder piece.
Roll the sleeves once or twice if the day is warm. It works for casual dates, weekends and relaxed offices, and I’d reach for it before a tee when I want to look a bit sharper.
10. Classic White T-Shirt
A plain white crewneck tee does more than almost any other shirt you can own, and it costs little to get right. Pair it with blue jeans and a baseball cap, and the outfit is done.
Pick a white that is thick enough not to show through, with a collar that lies flat.
Keep the cap simple, in a solid color with a small logo. Replace the tee when it yellows, because a dingy white looks worse than any other color.
Choosing the Right Fit
Shoulder seams decide whether a shirt fits. They should land at the edge of your shoulder bone; if they droop toward the arm or pinch up toward the neck, no amount of tailoring at the waist fixes it.
Check the collar too.
Hem length depends on how you wear the shirt. A longer hem is meant to be tucked, and a shorter one looks neater left out.
Buy for the way you will actually wear it, and have a tailor take in the sides if the body runs boxy for your frame.
Fabric Considerations
Cotton breathes, holds a crisp collar and is easy to care for.
Linen is the better call once the weather turns hot or humid. It is light and airy, and it looks best cut a little loose rather than slim.
If you wear linen to a summer wedding, make sure the suit is relaxed enough to match, since a stiff suit makes a linen shirt look out of place.
Styling Tips
Start with the occasion, then match the shirt’s formality to everything else you wear. For work or formal settings, stick with classic whites and blues, small checks and stripes, worn with dress trousers.
For casual days, earthy tones, bolder colors and wider stripes sit well with chinos or jeans.
A crew neck tee with jeans and sneakers is the easy, laid-back version. Layer the same tee under a blazer and it moves up to smart casual, with nothing else changed.
Frequently Asked Questions
What are different types of shirts called?
Men’s shirts go by names like dress shirt, overshirt, flannel, Cuban collar shirt, printed shirt, tank top, tuxedo shirt, Henley, casual button-down and white crewneck tee.
They split roughly by formality: dress and tuxedo shirts at the top, button-downs and Henleys in the middle, tees and tanks at the casual end. Pick by the occasion first, then by the fabric and fit.
What is a Henley shirt?
A Henley is a collarless shirt with a buttoned placket below the neckline.
The placket gives it more structure than a tee, so it sits between a tee and a button-up. Cream looks softer than white, and it works untucked or half-tucked with the top buttons open.
What type of shirt is best for hot weather?
Linen is the best call for hot or humid days because it is light and airy.
It looks better cut slightly loose than slim. Sleeveless tees suit the gym, beach and casual summer outings, while thick flannel belongs to cold weather only.
What is a tuxedo shirt?
A tuxedo shirt is made for black tie, and its pleated front is what separates it from an ordinary dress shirt.
The classic version is white with black studs, worn with plain dark trousers so the pleats stay the focus. Save it for formal events, since it looks out of place elsewhere.
What shirt should I wear to a casual date or the office?
For casual dates, a long-sleeved button-down worn untucked is a safe pick, in a color like rust over light blue or mid-wash jeans.
A Henley or a printed shirt also works on dates, though a print is less suited to the office. For work, stick with classic whites and blues or small checks and stripes, worn with dress trousers.
How should a men’s shirt fit?
Shoulder seams decide the fit, and they should land at the edge of your shoulder bone.
If they droop toward the arm or pinch toward the neck, tailoring at the waist will not fix it. Hem length depends on use: a longer hem is meant to be tucked, a shorter one looks neater left out.
