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.


At the Airport

The glory days and romance of airports and train stations are long gone. Today, travel is about long lines, crying children, mediocre food and the occasional inglorious sprint to one’s gate. Still, we persevere and try to look good doing it. Really it comes down to this: Versatility and Comfort.

Today’s post is about the first portion of the trip, the airport or train station. The latter is much less of a hassle, but either way, the rules are this: comfortable shoes, dark clothes, a good blazer, and a good bag.

Shoes. No monkstraps. Yes, they look great but they are a hassle to take on and off. Surviving the airport is about efficiency and monkstraps are anything but. If traveling for work and it is a short trip, then I usually only bring one pair of shoes and they are nearly always black dress shoes as the suits I will be wearing for meetings are nearly always dark.

Fun tip: Switch out the laces to something colorful while traveling and switch back to dark laces for the work meetings.

Dark Clothes. Travel in darks. Three reasons: They are easy to match and it isn’t the end of the world if you spill something on yourself. Plus, it’s tough not to look good in black. I like a good pair of dark jeans or chinos–they are comfortable, they don’t wrinkle easily, and I can wear them with most anything. I match that either with a button-down shirt or a polo.

Travel Garb

The pocket square and laces add the pop to an otherwise conservative outfit

The Blazer/Sweater. I love wearing blazers while traveling as it classes everything up and you can use a brightly-colored pocket square to show some personality. However, once you are on the plane, unless you are in first class, there is the question of what to do with the blazer–fold it and hold on to it? Wear it and wrinkle it up? Fold it and stuff it into the overhead? If it’s too much of a hassle, there is the simple and clean v-neck sweater as an alternative.

Elevator Selfie

The Bag. For trips under three days, I tend to go with the mantra of “What Would James Bond Do?” and let me tell you something: He wouldn’t own a rolling suitcase. A weekender bag looks good, it’s distinctive, it easily fits in the overhead, and it forces you to pack light. Finally, it’s a god damn conversation piece. Look at that bag. It’s gorgeous.

Jack Spade's waxwear weekenders.

Jack Spade’s waxwear weekenders do wonders.

Loud Whispers

September’s warmth in DC belies the onset of autumn, but it helps us ache in anticipation for leaves changing colors, cool autumn breezes, and layers. Autumn is my favorite season for many reasons, but from a sartorial perspective, I like it because of the layers and how it maximizes my ability to play with color, textures, and styles. The seasons are slowly changing here and autumn’s possibilities and opportunities are so close.

I came across one of my favorite quotes years ago while reading the Sartorialist. It goes like this: Elegance is something that must be whispered and not shouted.

That is the balance I am looking for in my own personal style. On a not-unlimited budget and working in a corporate environment, how do I set myself as distinctive but also comfortable? How do I show off bits of my personality in my work-wear to my clients and coworkers, but not distract from the work side of things? The same thing applies when out of the office: Fashion is not everything for me, but it presents a great opportunity to show splashes of one’s personality and to whisper–sometimes more loudly than others–about one’s elegance and style.

Work Wear

That is what I want to examine here on 12minds. A balance between affordability, distinctiveness, and the occasional splurge. I want to figure out what fits, what works, and why it works.