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.

The Oxford Button Down Dress Shirt

This article is part of my Men’s Wardrobe Essentials series.

One of the best collared shirts to own and what I recommend for all my clients, regardless of age or body type, is the Oxford Button Down Shirt. It’s versatile, comfortable and one of the more durable items you’ll have in your closet.

What is an Oxford Shirt?

Oxford Shirt vs. Dress Shirt – What’s the difference?

In my best Jerry Seinfeld voice: “So what’s with all these dress shirts?”

A dress shirt is any type of collared shirt with a stiff collar and long sleeves that may be worn with a suit or blazer. An Oxford Shirt is usually considered a type of dress shirt, but the Oxford shirt is different from a regular dress shirt in two ways:

  1. They usually have a button down-style collar which eliminates that problem of collars flopping around and/or laying flat and disappearing underneath a jacket’s collar.
  2. The Oxford Shirt is named after the specific weave of the fabric called, you guessed it, Oxford cloth. It has a basketweave structure and a lustrous aspect making it a popular fabric for a dress shirt.

While you can wear Oxford shirts with suits, I don’t dress my clients this way. The buttoned-down collar lends a more casual vibe to the shirt and takes attention away from the formality of a suit. Unless you’re going without a tie when wearing a suit, it’s just not my preference, but it’s acceptable. I normally pair them with a Gray Notch Lapel Suit (no tie), Blazer, Harrington Jacket, sweater, or by itself with the sleeves rolled up.

Why Should I Own Oxford Dress Shirts?

Well, because they’re awesome. But most importantly, because of these 3 points:

  1. Looks Good, Is Versatile
    They look great on every body type and they pairs easily with the rest of your essential wardrobe. They can also be worn in casual and professional settings and feel equally appropriate. Roll up the sleeves and leave it untucked over a pair of dark wash jeans and you’ve got a casual outfit. Button the cuffs, throw on a tie (or not) and wear under a suit or blazer and you’ve got a dress shirt. It’s one of the most versatile shirts in a man’s closet.
  2. Comfort
    The oxford material is typically woven in a basketweave pattern which allows it to be soft and comfortable and less prone to wrinkling than typical dress shirts made of silk or silk blends.
  3. Durability
    Due to the heavier fabric and weave the shirts are very resilient and durable, as opposed to non-weaved fabrics like silk or silk blends. I’ve got clients who’ve been wearing their Oxford shirts for over 5 years and they look good as new.

How should an Oxford Dress Shirt fit?

An Oxford Shirt should fit just like any other dress shirt you own.

The Best Oxford Button Down Shirts For Men

Since they’re all generally made of the same fabric and weave, the color is what matters most.

For my clients, I only recommend two colors to start because they look good on every skin tone, can be paired easily with the rest of your essential wardrobe and will cover any situation where a collared shirt is appropriate.

The colors are:

  • Light Blue
  • White

Designer Options

Brooks Brother Milano Fit Button-Down Collar Dress Shirt

Rag & Bone Thom Browne Oxford Shirt

Budget-Friendly Options

Club Monaco Classic Fit Oxford Shirt   

Uniqlo Mens Easy Care Long Sleeve Shirt

3 Ways to Wear Oxford Button Down Dress Shirts

Brooks Brothers Milano Fit Button-Down Collar Dress Shirt

Levi’s 511 Slim Fit Stretch Jeans 

Daniel Wellington Classic Sheffield 36mm

Allen Edmonds Newland Ave Casual Belt

Converse Jack Purcell Signature Leather

Brooks Brothers Red Fleece Merino Wool V-Neck Sweater

Brooks Brothers Milano Fit Button-Down Collar Dress Shirt

Brooks Brothers Milano Fit Plain Front Trousers

Daniel Wellington Classic Sheffield 36mm

Allen Edmonds Poplar Dress Belt

Allen Edmonds Carlyle Plain-toe Oxfords

Brooks Brothers Red Fleece Micro Check Suit Jacket

Brooks Brothers Milano Fit Button-Down Collar Dress Shirt 

Levi’s 511 Slim Fit Stretch Jeans

The Tie Bar Solid Pocket Square with Black Border 

Allen Edmonds Poplar Dress Belt 

Allen Edmonds Carlyle Plain-toe Oxfords

Outfit Inspiration

Chambray Shirt, Sport Coat, Chinos, and Dress Shoes

The casualness of a chambray combined with the sharpness of a sport coat is a guaranteed to turn heads in the office or at any wedding. Wear an indigo button-down chambray shirt, a grey wool sportcoat, blue chinos, and black oxford dress shoes. Spice things up with a lively pocket square and a simple plaque buckle belt.

 

Designer Options

Budget-Friendly Options