Oxford Cloth shirts in a Pink University Stripe with a Button Down Collar. Let's break that down.

Oxford Cloth is crunchy and soft. If you're moving on from cheap, papery poplin in your casual shirts, even the cheaper oxford cloth will feel like a revalation. Nicer oxfords, especially, can really be downright pleasant on your skin, even if you're coming from tee shirts.

And a good button down collar—especially one with a good collar roll—can bring enough interest to the table to make an otherwise unremarkable shirt speak volumes. It can look great without a tie—and, despite what some like to say, it can look great with a tie as well.

So far, we have an OCBD. Already an absolute classic. The first piece you recommend to somebody who wants more casual button ups. More versatile than flannels, and distinctly mature, while still being easy to dress down, OCBDs can stay casual or play up into casual tailoring.

Solid white and blue are versatile, but what if you want something a little more interesting? University stripes are the next twist, and while you might start with blue, there's a whole rainbow of them worth exploring. Now, we're starting to explore ivy style—if you're not into it, on any level, you might want to look away.

While I certainly have respect for blues, reds, purples, oranges... even greens and yellows, I'm going to focus this album on one color in particular: pink.

There's soemthing about a pink shirt. Pink and purple are two colors, particularly in pastel tones and white-based patterns—that can help you expand past the oh-too-easy blues... while still being really easy to wear. They're not neon shades, they're not that bright orange shirt you winced away from—pink is the most subtle of the warmer colors, and really lends itself to a perfect balance of standing out and blending in. After blue and white, pink and purple are the first two button ups I'd recommend to any man.

To be clear: not every shirt in this article will be pink—there will be some reds, some darkish reds and purples. Red and white in particular often come out looking pink to me, so they absolutely count. Some might not be button downs, some might not be oxford cloth, but they're all here to help me make my thesis. Whether you're just dipping your toe into casual shirting or knee-deep in ivy / prep / trad or casual tailoring, a pink university stripe oxford cloth button down is an amazing step with which to branch out.

On their own

Menswear enthusiasts love layering, so these photos were hard to find, but I think they do the job. These shirts are absolute bangers.

This is a great place to start, but won't serve as the meat of the inspo album. You don't need help pairing a shirt with itself. For interesting inspo, we need to start looking at casual layers.

Casual Jackets

They look good with casual jackets in any color. I'm not sure there's a jacket in your closet that won't pair nicely with a pink OCBD. You know what? Try it. I'm going to issue the #ocbdchallenge, try to find a bad pairing, I'll wait.

Okay, that's a bit of a joke, there are definitely jackets so bad that not even the glorious pink stripe will save them. And probably even some good jackets that don't pair well—probably. Like, I guess track jacekts won't work right. But everything from navy safari jackets to olive military jackets to the camelhair lazyman work. Suede. Probably most leather jackets, although a grungy double rider is probably pushing it. And... How's my overcoat below?

My shirt here is from Spier and Mackay, made from their Lightweight Oxford in "red" university stripe. I initially got pink, but it was way lighter than I actually wanted. Factor in not only the white stripes at a distance, but the white threads present in the oxford weave. Particularly on Spier's lightweight oxford, a good amount of that white shows through, so you have to get very close to say—"oh, I see the red now." In practice, it's just a pink stripe.

Credit to Immanuel Sodipe for recommending that exact fabric—you see him in the cover and you'll see him again below.

With a Crewneck Knit

I'll mention knits again below, but right here... I know you can barely see the shirts, but Ethan's fit here did something for me, and I'm really happy with my own execution.

A crew neck, specifically, covers the collar. I miss the collar roll, but the resulting effect—the shirt just poking out in the way it does... There's something to it. In my fit, it feels like a strawberry on top of a nice soft cake. (Yes, Strawberry Shortcake is an inevitable sequel in my good humor series, but this article is more focused than that). Cream and pastel, call it palewave, but whatever you call it, wear it.

The grey crew on the right pairs with a paler pink for a more subdued vibe. Just a little more interest than the bare minimum grey sweater.

In Ethan's fit, the shirt kind of tones the sweater down. It's not just a statement colored knit, it's a layering piece in a mature, complex combination.

Below, Drake's pairs a big coat, crew neck sweatshirt, and even a tie. The sweatshirt is a clear statement about casual ivy.

Casual Tailoring

I think most of the fits here are pretty casual, but I'm dividing the tailoring sections primarily about whether or not there's a tie involved.

Here, we see pairings with browns, dark and liht grays, olive, cream, and navy. Again, really remarkable color versatility.

I usually don't see them with suits—it's not that they're too casual, but maybe that you want a little more visual interest when your shirt is so... agreeable. The suit pairings I have all come below with neckwear. That makes sense to me—one extra pieve of interest is enough.

Tailoring with a Knit Layer

All four of my photos here are Drake's. Shirt-Knit-Layer is like a cheat code. I associate the vibe with guys like Gerry Nelson, too, but it's part of the secret sauce that makes Drake's styling legendary.

Personally, I prefer the crew necks. Something about sharp lapels, a soft curved crew neck, and the oblong collar jutting out... the shapes contrast in a way I love. But the V-necks certainly have some charm too.

Of course, getting everything to fit right is the trick. If your jacket fits slim without a sweater, it probably won't fit well with a robust layer in there. Try to look for relaxed layering. Figure out how you like your shirt and weater necks to interact, how you want them to fit.

It's most likely easier to get the fit right with the knit cardigans / vests below, but it's also a vibe I consider a little stuffy, a little nerdy. Again, though, it's got its charm. This tends to work better with a tie—the cardigans are lower cut than most v-necks, making room that could definitely stand to be filled.

Tailoring with a Tie

You might think of oxford cloth as stricly casual, but that's a little silly. They were casual in a time when tee shirts were strictly underwear. When casual would often still include a repp tie and jacket. Since then, we've only explored new ways to make tailoring more casual; why force rules today that were never rules before?

Besides, it can look damn good. Proportion is a big factor, as Ethan demonstrates here, You have to know whether you're going for an ivy vibe—repp ties, navy, khaki, etc.—or something more modern, or even going for something actually dressy.

Ethan above and Mark Cho below wear navy suits, pink OCBDs, and solid ties. The armoury fit above, and again Mark Cho below, wear khaki suits with chest patches—okay, not too dressy, but still, they're suit-and-tie combos.

Immanuel, meanwhile, loves a dressed down ivy. The club tie and baseball cap on the left is a very fun combo.

These fits are similar. Brown textured jacket, navy ivy tie, shirt buttons unbuttoned. But I think they each display the shirt well, and say something interesting about casual tailoring. And there's a reason I went for this shade of pink, rather than a paler pink or a darker red/purple. Again, this is Spier and Mackay's lightweight red oxford, which I bought mtm thanks to his recommendation.

I love Will's grey check DB here. Idk, the proportions of grey, pink, and navy in both photos just felt right to me. The cream jacket outfit is perfectly good too, of course.

Below, we've got some close-ups on collars and ties, just to drive the point home: they do work well together.

Conclusion

Versatility may be overrated, but here we have something both versatile and interesting. I'm betting a pink shirt can lend variety to your wardrobe in terms of color, and a colorful university stripe OCBD could help you explore a few different styles.

If you just want a basic casual shirt, this is about as good an option as any blue or white. You can wear it alone or layer it with most of the layers you already have lying around.

If you're looking to explore casual tailoring, you need to play with colors, and a pink stripe is interesting enough to play with while pairing easily enough that you'll never run out of options.

But you know what? I spent some months building this album and weighing my options before picking who I wanted my shirt from, and exactly what details I wanted. I'm happy with the result, and although I think you would be too...

If you really want a shirt that will make you happy—consider the details for yourself. Collect your own inspo. Read people telling you what they like, and see if you agree. Maybe you want a green stripe. Maybe you want linen. Maybe you want a western rayon shirt with pearl snaps. Shoot, I want one of those too.

I hope I've either convinced you to get a pink university stripe oxford cloth shirt with a button down collar... or helped you recognize the details that enable you to pick your next piece well. Either way, let me know... But in case you want an OCBD:

Buying

• Spier and Mackay's Lightweight Red University Stripe Oxford, worn by Immanuel and myself above. Off the rack or MTM. Use my code, E4HPYF, for 20% off your first order. Oh, and they also have a "red bengal stripe linen" and some other alternatives.
• Brooks Brothers, though it ain't what it used to be.
• Proper Cloth
• Drake's
• J. Press... doesn't really have a pink. Their red actually reads as red. Still worth mentioning.
• Anglo-Italian is also a true red.

Further Reading

• The Soft Rolls of the OCBD & Button-Down Collar - A Little Bit of Rest
• How to Talk About Collared Shrits - Dress Code
• The OCBD Shirt Series, Part II: The “Golden Era” Oxfords