One Shirt Four Ways: 4 Full Outfits Using One OCBD

Oxford cloth button down shirts

One of the essential skills for building a versatile wardrobe affordably is learning how to use any single clothing item in a variety of ways. This magic allows you to utilize a single shirt into several outfits that range across the style spectrum from rugged casual to business casual. Today we will look at how to use a basic gray oxford cloth button-down shirt in 4 very different outfits.

Any oxford cloth button-down shirt is really versatile and these are a great addition to any wardrobe, but they are especially helpful when you are just building your wardrobe precisely because you can wear them with almost anything and they always look great.

The oxford cloth button-down shirt is known colloquially as an “OCBD” and referred to that way across style blogs and forums. They differ from a “dress shirt” due to their thicker and rougher fabric. They have tiny buttons on the collar which is where the “button-down” part comes from, not from the fact that they have buttons on the front.

If you are just beginning to build a wardrobe, the OCBD is a perfect shirt to add. They come in a wide range of colors and fits and you can find them at every price point. For me, affordability is a really important consideration, so I love that I can often find OCBDs for sale for less than $20. Blue and white are probably the most common colors, but today we will consider the versatile light gray color. We’ll see that this one shirt looks great with everything from jeans to dress slacks and a tie.

Rugged Casual Style Outfit
~Rugged Casual~

Invicta Dive Watch ($88). Uniqlo Oxford Shirt ($29). Goodfellow & Co. Lyndale V-Neck T-Shirt ($5). Cole Haan Feathercraft Grand Boot ($90). DSLTD Slim Jeans ($75). Timberland Casual Belt ($21). Pendleton Crew Socks ($14).

Starting at the most casual end of the spectrum, we layer our gray OCBD over a plain t-shirt, with dark jeans, and boots. I always wear my shirts tucked in, but this would be a great look with an untucked shirt. Many guys just beginning to improve their style think any shirt with buttons on the front is “dressy”, but this look smashes that myth for several reasons. Rolling your sleeves immediately pulls the outfit into a more casual mode. Boots always look slightly rugged and casual, especially when they are suede like this pair. And leaving the shirt half-buttoned with our plain t-shirt peaking out literally keeps things from looking too “buttoned-up”. (#dadjoke)

Casual never has to mean sloppy.

Casual butch style outfit collage with watch, classic sneakers and aviator sunglasses.

Timex Weekender Chronograph ($52). J.Crew Slub T-Shirt ($34). Amazon Essentials Oxford Shirt ($18). PUMA Suede Classic Sneakers ($65). Goodfellow & Co. Hennepin Chinos ($23). MXNX Aviator Sunglasses ($15). Falari Woven Belt ($8).

Moving along the style spectrum, this outfit hits all the right notes for a great put together casual outfit. This is no more stuffy than a “jeans and t-shirt” casual outfit. But it IS a lot more intentional and arguably a bit more mature looking. Here we layer our OCBD over a light t-shirt again. The stripes on the t-shirt make the combo really casual. The chinos are also very casual due to their loose fit and the olive green color. As always, a belt pulls together an outfit. To keep this from looking “dressed up”, we use a woven belt in a natural color. The classic sneakers make the final statement that this is an intentionally casual outfit. Casual never has to mean sloppy. We can choose items with a slightly looser fit and colors that convey our intentions to look casual, but still well-dressed.

Smart casual outfit collage with boots, khakis, Timex watch and sweater.
~Smart Casual~

Lands End Tailored Fit OCBD ($19). IZOD Mock Neck Sweater ($63). Field Notes Brand National Parks Memo Notebook ($13 for a 3-pack). Memento Mori Medallion ($26). Dockers All Season Tech Pants ($37). Prospero Belt ($22). Nunn Bush Odell Wingtip Boot ($75). Pair of Thieves Socks ($15 for a 3-pack). Timex Waterbury Watch ($85).

Now we will take things up one notch to “smart casual”.  To me, smart casual is mixing elements many people consider to be “business casual” such as chinos with items that are definitely casual like a jean jacket.  Primer Magazine (one of my 7 favorite menswear blogs) did a fantastic post on smart casual here so check that out to get your head around the term. The key here is intentionally mixing elements from the full range of the style spectrum.  

From top to bottom:  We start with our gray OCBD as the base, of course.  Layering a thick henley sweater adds elements of both casual (layering) and dressy (the sweater is dressier than a sweatshirt).  The chinos in this outfit are a slimmer cut and slightly more structured material. The outfit is grounded and defined by the wingtip boots.  Wingtips are seen today as a kind of dress shoe though they got their start long ago as hunting gear. As boots, they are inherently a bit more casual than oxfords or dress shoes, but as wingtips, they are dressier than work boots or sneakers.  

Business casual with oxford cloth button down, Orient Watch, patterned tie and dress shoes.
~Business Casual~

Warby Parker Hawthorne Glasses ($195). Orient Capital Version 2 Watch ($68). Haggar Slim Dress Pants ($33). Stafford OCBD Dress Shirt ($22). The Tie Bar Floral Span Navy Tie ($25). Cole Haan Lenox Hill Split-Toe Oxford Shoes ($73). Marino Avenue Dress Belt ($15). Gold Toe Milan Dress Socks ($10).

Lastly, we look at the gray OCBD in a business casual outfit. The shirt material is a little rough to be dressy, so we dial up the other elements of the outfit to bring everything up a notch to business casual. A tie always establishes that you’re trying to look fancy. I love this subdued floral pattern. Sometimes using a very spare touch of color like the rosy dots on this tie is more effective than using a really splashy accessory. All of the other individual items here are dressy: the split toe oxford dress shoes, the dressy black watch, the slim belt, and even the plain dress socks. We build an outfit based on intention and the use of dressier elements works perfectly with our trusty OCBD. When you walk through the halls of your office wearing this outfit, every heel click on the hard floor will announce that you feel like a boss.

We build an outfit based on intention.

Now we’ve seen how to use one shirt across the range of the style spectrum from rugged casual all the way to business casual. When we start stocking our closets with choices that are truly versatile, we really expand our ability to create a wide range of outfits that are appropriate for a variety of situations. This gives us a greater ability to be creative with our clothing without spending money on things that only work in one circumstance or occasion. I hope this is a helpful demonstration of how versatile items can be worn thoughtfully and intentionally to get the most out of every piece of clothing we own.