The line between being overdressed and underdressed is a tricky one to follow.

Wear the wrong item, and you might stick out like a sore thumb; underestimate the situation, and stand out in a negative way.

There are few items that bridge the gap between the two areas, but there are certainly solutions to the problem. As far as classic style staples go, men have been wearing white shirts for centuries.

And as far as items that bridge that “overdressed or underdressed” gap, a white Oxford cloth button down, or OCBD, fits the bill nicely.

Sure, there are other, more colorful OCBDs and shirts, but for starting out, a white option is most versatile.

Sounds boring and antiquated, right? Wrong.

There are a lot of ways to freshen up the typical ensemble, by amping up color and nailing the fit and proportions. The ideal white shirt should fit slim, but not tight, with high armholes and sleeves that skim your arms, shoulders and chest.

Trying on multiple varieties of shirts can be very helpful; one store’s version of a shirt might not fit the same as another store’s version, even in the same size.

Finding a style that works to accentuate your body type goes a long way in making an inexpensive shirt look great.

Keep that in mind as you shop, and don’t be afraid to size down. If it means taking your measurements, all the better.

“What about fabric?”

white_ocbdFabric types on a white OCBD are a bit of a conundrum for some folks. There’s a debate about soft-wash versus other types of OCBD’s; the pre-wash gives it a more lived-in feel and texture, whereas shirts without that type of wash allow you to do some of the breaking-in yourself.

Soft-wash types of shirts are also slightly less dressy and would probably work best under a sweater or blazer because of the textural differences between an OCBD without a soft-wash (like these Old Navy options), but both are relatively interchangeable.

Either type would work well with any of the combinations below. Like most things in fashion and style, it’s all a matter of personal preference.

“How should I care for my OCBD?”

Some OCBD shirts are marketed based on wash or as a non-iron shirt, but ideally, every shirt should go through some sort of ironing or hang-drying after washing.

With higher-quality fabric, like a custom shirt or a number from J. Crew, there’s less chance of the fabric being damaged or worn out with multiple washes; however, some more inexpensive options might deteriorate more quickly with extra washes.

It’s best to judge when it’s time to wash a shirt like this based on look and feel; stains should be treated as soon as possible, and washed with whites, not other colors (even if washing the entire load on a cold setting).

Utilizing a shirt rotation helps too; if you love white OCBD’s, it could also be best to stock up on a handful at the right price — that way, you have one when you want it! But first, let’s figure out what to wear with this shirt.

1. Polished Business Casual


This look could be one of the more versatile, office-ready get-ups in your arsenal. That solid white color of the shirt in a slim fit like the Old Navy option pairs with any color you can think of in terms of pants and tie. A tailored pant like the Alpha Khakis helps keep everything in proportion with a slim top.

Some are against wearing just a shirt and tie, but rolling up those shirt sleeves the right way, and pairing that look with a knit tie (more casual to begin with), avoids the “lost-jacket” look.

Now, the key with your pants and tie revolves around complementing those colors; with a blue or red pant, a grey knit tie, while safe, would be a nice match in terms of neutrality, but getting into a small pattern in your tie might not be a bad choice either.

(Ed. note: The cap toe shoes pictured here would work, while a wing tip would be a more casual alternative.) And in keeping with the casual theme of the outfit, a wing tip shoe with its perforations, is polished and remains less dressy without being too loud.

2. Going Tie-less


Using that same Oxford cloth shirt can take you a lot of different places. Like any great outfit, this one is as versatile as it is polished.

Taking that white OCBD and pairing it with a well-fitted blazer is another business casual option that would also work for, say, dressed-up drinks or a nice date. Using an OCBD with a collar that doesn’t flop can be a tricky test, but higher-quality shirts seem to avoid that problem.

That blazer might need tailoring, but sizing down (or up?) could help out some guys, too. Jeans in a slightly different shade (maybe with a slight amount of distressing), will help break up some of the blue-on-blue look, and an unstructured blazer means the outfit leans slightly more casual.

To further break up some of the blue-on-blue combo, a a stand-out pocket square could do the job. Anchoring the look with a solid, no-nonsense suede desert boot is a safe bet.

It provides the perfect outlet to play up your sock game a bit, and a rich brown suede adds more visual depth to the outfit; make sure there’s not too much clash going on between the pocket square and the socks, too.

3. Day Out


So, if you feel like throwing on a shirt with a collar to head out for the day, but don’t want to go full-on suit and tie, this outfit could act as a nice in-between.

That Harrington-style jacket is a touch on the pricey side, but scouring eBay or Amazon might lead to a better deal, and if you do feel like paying top price, they’re more than worth it (an item from the personal collection still sees heavy rotation even after hard wear). A Harrington-style jacket is about as classic as it gets; it’s versatile and functional in the weather, too.

Dark denim is nice go-to for anchoring any outfit, and here, there’s some good color contrast with the grey jacket. The braided leather belt, while not immediately visible, adds some good texture to the top half of the ensemble, too.

The chambray sneakers might be too close in color palette to the jacket, in which a pair of white plimsolls might work instead. Again, topping the outfit off with some wild, patterned socks throws in a much-needed pop of color without overdoing it.

Could also be a good time to experiment with a different-colored watch strap, too.

4. Warm Weather Casual


With this outfit, there are some key choices that can take it up a notch or two.

Since the outfit is meant to be worn casually, you might want to leave that shirt untucked. It should hit the right spot, though (if the shirt is past your crotch, it’s too long to be worn untucked).

The right shirt falls below the belt, yet has a tail that’s not too long. If you’d like to tuck the shirt in, a textured belt similar to the outfit featured above would work nicely, as would a belt with a stripe of color.

On your feet, keeping your shoes low-profile and neutral definitely makes sense, particularly if you have some different pieces of color working up top.

Again, pay careful attention to your wrist watch — going with colorful shorts? Dial back the strap appropriately; (if you have a Timex Weekender, here’s an opportunity to use a slip-thru strap in a neutral palette, like this.

5. Cold-Weather Casual


This is another combination that’s pretty simple and straightforward. The pieces in this outfit could easily be swapped out for a different shade of boot or a different colored sweater, and that blazer from the second option could feasibly be thrown on over this combination, too.

It’s sort of a hybrid when thrown together with some beat-up boots (business casual on top, workwear stylings on the bottom), which isn’t for everyone. The white shirt’s neutral shade lends itself well to pairing with a more dynamically-colored sweater, even in winter or colder weather.

Again, dark denim acts as a visual, almost neutral anchor for the piece. The boots add just enough interest when it comes to texture. If you have a nice rotation of sweaters and dark jeans, and a pair of sturdy boots, this could be the ideal outfit for trooping around in the winter when you’re off-duty.

Wearing a solid white shirt like this effectively comes down to your willingness to experiment with colors and textures.

Using subtle variations of items you may already have in your wardrobe (like trading a silk tie for a knit tie, or a plain leather belt for a braided one), helps add visual contrast to an outfit, which can perfectly complement a crisp, white shirt.

As always, care and fit are key, too.

What are your favorite things to wear with an OCBD?

Let’s hear it in the comments. If you have any other suggestions on additional outfits, would love to hear those as well.


Beau is a senior editor at The State News, Michigan State’s student newspaper. A #menswear enthusiast, Beau can be found on Twitter (@BoKnowsClothes). He also writes about men’s style at Siblings With Style.

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PUBLISHED September 12, 2013

A Michigan State University alumnus, Beau works in the fashion division at New York City's Coyne PR. In addition to writing for Effortless Gent, Beau's menswear writing has appeared on Dappered, VOUCH Mag, and GearHungry. He also runs his own blog, The Style Guide.

  • arguson

    I love throwing a colored henley instead of a standard sweater over a white ocbd paired with some neutral chinos and brown brogues.

  • Tristan

    Love wearing white shirts, but after a few worn, my armpits become yellow, even while wearing an undershirt. Any tips on that? I’m kinda trapped in the fact that I want to pay for quality while knowing that in a few weeks, it we be completly burn.

    • Martin
    • second @martin’s suggestion!

    • Jackson

      The aluminum in your antiperspirant is what’s discoloring your clothes. Consider using just a deodorant. Seems counter intuitive, I know, but after making the switch I’ve found that I don’t sweat any more without antiperspirant. In fact, I think the antiperspirant actually made me sweat more. My armpits aren’t irritated anymore and my shirts don’t stain. Try it for a day or two, see how it feels.

  • Funny timing, since I also got this in my email this morning:

    Love these pairings, EG!

    • h/t to Beau for coming up with all of them!

  • Excellent tips, but please have my thanks particularly for the technical words for each of those garments.

  • Michael

    I love these “5 Ways to Wear One” posts. Please keep them coming in relation to mens essential clothing item list.

  • Excellent post indeed, as someone who’s looking forward to renew almost the entire closet, OBDS is certainly a big part of its new content and these pairing options are highly helpful 🙂

    • Glad it’s helpful, David!

  • Tim

    Nice post! I’m sure someone has already mentioned this to you, but the shoes shown in #1 aren’t wingtips. I agree, however, that brown wingtips would look better with that outfit.

    • Good catch; that was my fault. I switched the wing tips out for these cap toes last minute, forgetting to acknowledge that in the article. Adjusted above. Thanks!

  • victor

    hey barron, what do you think of those loud shirts out there with all the wild colors.. ? .. I prefer simple shirts in white and navy and using accessories ..etc,…bright socks, bright and colorful watch to give it an edge..always felt uncomfortable wearing those shirts in the past and looking to tone it down..

    • Are you referring to the Robert Graham style shirts (, for example? If so, I feel the same as you. I like pretty basic main garments, but accenting with more interesting, “louder” accessories.

      • victor

        exactly…I remember when these shirts were ” in style ” a few years ago, but just felt strange wearing them with many people staring at me .. not even comfortable with ocbd in loud colours , like orange and bright green, but to each his own I gues…

  • james

    First, thanks for these posts. Posts like these with lots of visuals and links really help!

    Now for a question: when we talk about OCBD, does that specifically refer to regular oxford or can it include pinpoint oxford as well? I understand pinpoint is a little finer yarn and results in a smoother more dressier shirt than regular oxford. I like option 1, the polished business casual with the OCBD and chinos look and was just wondering if it matters if the OCBD is regular or pinpoint or if I should be looking for one over the other or can they both work for this look? Thanks for the help! Really appreciate these posts!

  • Dj Mindtricks

    As a teenager, I usually pair an OCBD with a simple zipup hoodie or rain jacket (I usually wear my Superdry Windcheater). I also like to go without a tie and wear a cardigan and parka over it for colder weather. I’ve learned from thrifting and several embarrassing underdressed/overdressed moments during high school that simplicity certainly goes a long way, and an OCBD is an absolute essential to any wardrobe.

    This post was genuinely helpful and is just a beginner’s guide to a plethora of style options. Thumbs up!

  • OSanz

    Can you wear an oxford shirt during winter? Or is it more of a summer shirt?
    Thank you.

    • I wear mine year-round!

  • ds87

    I bought a nice Jcrew White OCBD, but I find that I don’t feel confident enough to pull it off. I feel like I stand out so brightly and it seems to “dressy” even with jeans. I am fine with wearing ANY other color and style except this shirt. Any Suggestions?

  • Marc

    I know I’m late to the party, but it’s at least a seasonally appropriate response. I like wearing a wool sweater (preferably Shetland wool) or shawl collar cardigan over an OCBD with chinos, cords, or jeans and chukkas or bucks.