The Best Shirts to Wear on Casual Friday

Aren’t Fridays the best day of the week? Fridays bring one last shift before the weekend, plus the chance to dress down if “casual Friday” is an institution at your office. While you may welcome the chance to ditch the full suit in anticipation of the weekend, it may not always be obvious what you should wear on casual Fridays, especially if you pride yourself on your sense of style throughout the rest of the week, or are worried about dressing down in case you need to take a surprise meeting or deal with an unexpected visit from your boss’s boss.

But keeping things appropriate for a last-minute meeting doesn’t rule out having a little bit of fun with your Friday ensembles. The best way to participate in casual Friday without throwing out your sartorial standards is actually pretty simple: just swap out your usual shirt for something a little bit more fun. It’s a strategy that works whether you wear a full suit and tie, or a pair of chinos with a sweater. Here are some pointers that will help you find the best shirts for casual Friday, plus a little wisdom on how you can look sharp but still have a little fun.

Choose a new pattern or texture

W.R.K. nepped oxford shirt


The most important thing to keep in mind when standing in front of your closet on Friday morning is what your office’s policy is. This varies a lot from workplace to workplace, and the standards will be very different at a casual office versus a formal one versus a creative one. (If you’re in doubt about what you can get away with — in terms of color and pattern — just look at what your boss is wearing.) If he mostly sticks to solids and stripes, then you know those are safe choices. Are you regularly sighting gingham or other small patterns, or even multi-color patterns? Then you can have a little bit more fun.

You have lots of choices of patterned shirting, even if you need to stick strictly to dress shirts, rather than branching out to sport shirts and their more casual fabrics. Consider a mini gingham, such as the one featured by this slim-fit shirt by John Varvatos, or a larger check like the one seen on this shirt by Thomas Pink. Alternately, consider a dot print like the one on Burberry’s slim-fit dress shirt, or a bolder plaid like the one chosen for this dress shirt by Todd Snyder. Or, especially in a creative workplace, consider going less traditional with a maple leaf print from Club Monaco or a burgundy floral from J. Crew. If none of those patterns are your style, opt for some extra texture instead of a geometric pattern by going with a shirt like W.R.K.’s nepped-yarn oxford shirt.

Experiment with a wider range of colors

Ralph Lauren slim-fit cotton shirt


Even if your boss is all about patterns on Fridays, you may not feel comfortable in them, and that’s OK. Your casual Friday ensembles should be about having fun with color. Especially if you normally shy away from color during the first four days of the week, consider experimenting. Think of the colors you like to wear when you aren’t held to the strict standards of your manager’s dress code. Your casual Friday ensembles should still be appropriate for your office, but should display a little bit more of your personal style than you’d show on other days of the week.

If you default to a light blue shirt most of the week, consider a darker, classic navy for Fridays, like Ralph Lauren’s slim cotton shirt. A light chambray, like this year-round classic from J. Crew, is a good way to branch out from your usual dress shirts, since it’s so easy to pair with other office staples, from dark suits to tan chinos to classic sweaters. A dark green shirt from NN. 07 or a tan button-down from Gant Rugger are excellent choices for guys who want to try more unusual colors in familiar styles. Or, if you’re really a minimalist when it comes to incorporating color into your wardrobe, opt for a subtle style like this unique grey shirt from Club Monaco.

Stick with neat, comfortable fabrics

Ralph Lauren slim cotton oxford shirt


Especially when you’re dressed down more than you’d usually be, it’s important to make sure that your clothes are high-quality, fit well, and are both clean and wrinkle-free. Keeping your shirt neat is as easy as paying attention to what fabric it’s made of. It’s always a good idea to choose one made of cotton for the easiest maintenance. You may be tempted to go with whatever says “wrinkle-free” or “non-iron,” but those aren’t always the most comfortable shirts. In fact, one of our favorites is plain oxford cloth, which is easy to keep looking smooth thanks to its thicker hand, tendency to come out of the dryer without major wrinkles, and the button-down collar often found on shirts made of the fabric.

The oxford shirt is, at least traditionally, a sport shirt and not a dress shirt, which makes it a great candidate for a casual Friday shirt, especially in more formal offices. An excellent place to start when shopping for an oxford shirt is none other than American classic Ralph Lauren, where you can find oxfords not only in light solid colors, but also in brighter solids, classic stripes, and darker solids that are perfect for fall and winter. Just bear in mind that even though an oxford shirt is less prone to wrinkles than other types, it’s still a good idea to steam your shirts, iron at minimum the collar, placket, and cuffs, or at least remove them from the dryer promptly.

Find a shirt that offers the right fit

Brooks Brothers tartan sport shirt


An important part of looking sharp while you’re dressed down is making sure that your clothes, including your shirt, fit impeccably. And that’s where it works to your advantage that many retailers offer the same clothes in a number of different cuts, which help guys of all shapes and sizes achieve a trim, tailored fit.

Consider, for instance, a basic oxford shirt from Brooks Brothers. The versatile cotton oxford is offered in three different fits: the extra-slim Milano, the slim Regent, and the classic Madison. Choosing the one you want is as simple as selecting a color when adding a shirt to your cart (though we’d recommend stopping by the store if you’re unfamiliar with the cuts or need a refresher on which is the most flattering on you). Oxfords are good any day of the week, but if you’re looking for something  a little bolder for casual Friday, consider a tartan sport shirt to wear with a sweater or tweedy jacket, available in the same three fits.

More from Gear & Style Cheat Sheet: