5 Shirts Every Man Should Own

Building a stylish, versatile wardrobe starts with a solid foundation, and with shirts, you want to find simple, versatile options that are timeless and go with everything. Don’t be afraid to buy multiple colors of the same shirt to take out over-thinking about wardrobe. These are the five essentials shirts that every man should own!

Don’t forget to check out our shirt Fit Guides for more info.

1. White dress shirt

Simple, timeless and will go with everything.  Every man should have a few crisp white dress shirts in his closet. Wear with everything from a suit to jeans.

2. Oxford

Another classic, make sure to get these in blue or white.  Oxfords are the ultimate casual staple for jeans or chinos and can be easily dressed up for business casual with a blazer.

3. Black T-shirt

I love the versatility of a black t-shirt.  It can be casual with jeans and sneakers or even dressed up with a blazer or suit.

4. Chambray shirt

This shirt has a cool, denim-like vibe and is perfect with chinos or as a more casual substitute for a dress shirt with a blazer and a tie.

5. Solid colored polos

Make sure you have a good rotation of solid-colored polos in basic colors like black, grey, navy, and white.

Bonus: Henley

A henley shirt is only recommended if you have a trim to medium build.  If you’re a bigger or athletic guy it’s not the right shirt for you.

Shirt Picks

White Dress Shirts:

Burberry

Brooks Brothers Milano Non-Iron

The Tie Bar

Uniqlo

Zara

Oxfords:

Norse Projects Oxford

Brooks Brothers Milano Fit Oxford

Club Monaco Oxford

JCrew Oxford

Uniqlo Oxford

Chambray:

Brunello Cucinelli

Saturdays NYC

JCrew

Banana Republic

Amazon Goodthreads

T-Shirts:

James Perse

Rag & Bone

American Apparel

Uniqlo

H&M

Polos:

Brooks Brothers

Lacoste

James Perse

H&M

Uniqlo

Henley:

Rag & Bone Classic Henley

Rag & Bone Giles Henley

John Varvatos

James Perse

J. Crew

H&M

How To Wear Patterned Shirts

Whether you want to level up your business casual and weekend wardrobe or complement dressy looks, the right patterned shirt can do wonders. No matter if I’m dressing my clients formally or casually, I rely on patterned dress shirts to add both style and visual interest to whatever they’re wearing, and I’m going to show you how to do it so you look great – every time.

First, a quick word on formality.  While it’s not a hard and fast rule, in a basic sense, the bigger or bolder the pattern, the less formal the shirt is. For most of you dressing casually or in business casual, you’re home free, most patterns will definitely work. But, for some of you guys that work in more formal office environments or if you’re dressing up for a fancy wedding or evening event, keep in mind that the more subtle patterns will be much more appropriate. So now that we’ve got that established, let’s get some patterns in your life.

Stripes

Stripes can come in all manner of widths, from wide (sometimes known as Bengal stripes), to medium (pencil stripe), to thin (pinstripes) and since they tend to lean a bit more conservative, they’re also an easy place to start if you’re new to the game.

How Best To Wear Striped Shirts

As a general rule, the wider the stripe, the bolder the statement, and just like matching colors, the bolder the choice, the more simply you should approach the rest of your look. For casual and business casual looks, a simple pair of chinos or dark denim is a great option.  I also like stripes when worn with solid-colored or textured suiting and under a solid v-neck sweater with dress pants, denim, or chinos.

Checks

The world of checks is a wide one, but there’s no better way to add some instant personality to your shirt arsenal than with a few carefully chosen checked shirts.  There are many different options available, but, in my opinion, the three with the most versatility and style are windowpane, tattersall, and gingham. Both windowpane and tattersall feature types of graph patterns that can range in size and thickness and gingham goes one step further with a bolder, thicker check pattern that often combines a base color like white and one other color.

How Best To Wear Checked Shirts

As with stripes, the level of statement can vary, but my go-to rule remains, keep the rest of your look simple.  Dark-colored denim, chinos, and dress pants are the ticket, and if you’re going to dress them up, I recommend solid-colored suits and solid or subtle ties. On the tie front, I think geometrically patterned ties can look a bit too matchy-matchy with checked shirts, so be wary. Protip: for a less formal tie option, try a knit tie in a solid, complementing color. The texture and slightly less formal nature of a knit tie work really well with blazers, chinos, and denim for a dressy hybrid that’s great for business casual or a dressed-down Friday.

Geometric and Floral Prints

Now more popular than ever, print shirts are a great way to add a cool, modern edge to your casual looks and even suiting and dress clothes. Small-scale geometric prints are a great place to start if you want to keep it subtle but, I definitely recommend trying a bolder floral print too, it’s an easy, fun way to add a bit of stylish personality to your vibe.

How Best To Wear Geometric and Floral Prints

The printed shirt is all about letting the shirt do the talking, so I highly recommend denim or dark chinos in navy, tan or gray, especially if you’re going with a floral print, and finish with sneakers or loafers (I like driving mocs). Don’t be afraid to dress up a printed shirt too, pair it with a slim dark suit and some penny loafers or dressy leather sneakers for formal-but-not-stuffy settings like a cocktail party, fun summer wedding or night out. For a black belt-level move, try rocking the air tie (top button buttoned, no tie).

Plaids

When you’re talking plaid shirts, usually the pattern involves multiple colors and lines/boxes and the more things happening with the pattern (color, width, etc) the better suited the plaid will be to casual dressing. Be warned, though, it’s a slippery slope to full lumberjack hipster, so chop firewood at your own risk!

How Best To Wear Plaids

Ultimately these patterns are busy, and I recommend keeping plaids casual and subtle, so try them with denim, chinos, and shorts in solid colors, and finish them with shoes like sneakers or chukka boots. You can always “turn down the volume” of a plaid by layering it under a solid-colored sweater, lightweight jacket or pairing it with a dark-colored blazer in dressier situations.

Now that you’ve got some know-how and a few tips in your pocket, have confidence and make these patterns work for you! Your shirt rotation (and your wardrobe in general) are about to get an upgrade.