Casual Friday

Casual Friday and Jeans Day is a bit of a strange concept for me. After all, in the office we present professionalism and adherence to the rules—the very conceit of the suit and traditional white-shoe firms is uniformity, rigidity, and conservatism. The Corporate world still holds that in high esteem.

And yet, we have Jeans Days and Casual Fridays. We now blend the line between formal and informal, ubiquity and uniqueness, and what we would wear in the workplace with what we would wear on the weekend. While some push back against the concept entirely and mourn the end of the well-dressed, I take a less intense approach: It is possible to dress casually and dress well. It is possible to wear jeans from time to time and not look like you’re desperately holding on to the glory days of college.

My general rule is that so long as jeans are worn a) sparingly and b) wisely, then jeans can have a place at the office.


This cannot be stressed enough: You are still at the office and you need to project professionalism. On the off-chance a client shows up or you have to present yourself as the face of your office, then you should look the damn part. If there is going to be any repeating theme in this blog, it is this: Context Matters.

Absolutely this not the time or place for your favorite worn jeans that you’ve had for ten years, your college sweatshirt, or your sneakers. If you are a Creative you have more flexibility than a Corporate. But still, if elegance is something to be whispered, then casual days at the office require the same concepts as formal days: Good fit, balanced, deliberate, and use of specific articles to show off your personality.

A favorite look for Casual Friday: Dark and slim profile with a single (and wonderful) pop of color. Emulate this.

A favorite look for Casual Friday: Dark and slim profile with a single (and wonderful) pop of color. Emulate this.

If you are going to wear jeans, keep them dark and without any tears. Otherwise I am a proponent of chinos–more modern than khakis and classier than jeans. Plus, you can play with colors. Check out the options on Bonobos or Banana Republic. They are affordable, they last forever, and you can use them for weekends with friends and weekdays at the office. For the top: a button down shirt, a bright tie, a v-neck sweater, and a blazer.

A casual blazer and a colorful v-neck makes all the difference.

A casual blazer and a colorful v-neck makes all the difference.

The key to the outfit is to make the pants and top clean and slim; this allows you to present a clear profile but also allows you to throw on personality in other ways: Watches, ties, socks, shoes, and the belt. Wear chukkas to a white-shoe firm, drop the brown/black belt and try out cloth belts, deviate from your standard grown-up and fancy watches to play with color. Watches deserve their own post, but I will say this: the Timex Weekender is probably one of my favorite things that I own. The watch itself costs under $50 and the straps are no more than $30. Buy multiple straps and play with all the different colors and patterns. It’s wonderful.

Seriously, go buy the watch and two or three watch bands immediately.

Seriously, go buy the watch and two or three watch bands immediately.


Here’s the thing: Just because jeans are allowed it does not follow that you need to wear them every Friday. Wear a suit, drop the tie, unbutton an extra button at the top, and wear colorful socks or funky-patterned pocket squares. Instead of oxford shoes, throw on loafers. Wear chinos and try out an extra colorful tie or blazer. The point is, rather than thinking of this as jeans day, consider it an opportunity to take chances at the office and to be decisive. Play with colors and fabrics; set yourself apart; own it.

Of Comfortable Boldness

Cardigans are one of those things that I cannot wear without immediately looking a) ten years older and b) thirty pounds heavier. It’s a dark magic and I cannot break the curse, but I do at least appreciate its consistency so I know to steer clear.

The man makes it work

If you’re going to try to pull this off, make sure the button-down shirt is fitted to the same length as the cardigan. Otherwise it will look slovenly instead of intentionally and carefully careless.

This relates back to style tips as follows: What works for some does not work for all; further, it is important to know what works for you. One of the points I will touch on a lot on this site is this: Style is about knowing yourself–what works for you, what fits well, and what makes you feel simultaneously bold but comfortable. Style is about articulating who you are and pushing the envelope enough to emphasize parts of your personality. That articulation requires the confidence to try new things, but also the confidence to buck trends. It’s a fine line and, as much as I like how it fits the guy in the picture above, it’s why I won’t be wearing any cardigans.