Outfit Of The Week 9/17/23-9/23/23

Here at FS, I am going to start highlighting some of the outfits I wear. I feel it’s helpful for the reader to see the advice on this page in action.

This week I made an appearance in the office. My office dress code is business-casual, as I suspect is the case for many of you. As we all know, that designation has very little meaning beyond “Don’t Dress Like A Slob”.

And, honestly, for all the hand-wringing done by internet weirdos like me about the death of classic menswear and the howls of “No one gets dressed up anymore!”, I hardly ever see anyone dressed totally inappropriately.

The operative word in that last sentence is “hardly”. In the communal space in my office building I saw one guy from another company in a tank-top and shorts. I saw a girl in a midriff top with the straps of her thong pulled up out of the waistband of her pants.

Classy!

Unfortunately, I feel like those individuals are going to look back on their early years in the corporate world and kick themselves for the time they wasted by dressing in a wildly inappropriate manner. No matter how good their work is, no one is going to promote Tank-Top Guy. No one is going to think that Thong Girl can handle important client meetings. These people are putting hand-brakes on their lives without even realizing it.

Ok, enough about them and on to me!

Since my office is business-casual, I opt not to wear a tie. Even though I like wearing ties, it would be a little out of place given that some of my coworkers (and bosses) are in jeans most days. This is not an example of timidly following the herd, though. This is an example of reading the room and dressing in a way that fits the occasion. It’s important to know the difference.

Some time ago, I wrote an article on the perfect business-casual uniform, and I stuck to a similar formula here.

The centerpiece of the outfit is a navy blazer from Brooks Brothers. I got this jacket three years ago (on sale!) and only had the chance to get it tailored last year. Honestly, I might have my tailor let it out a bit, as it pulls slightly around my lats and causes the lapels to wrinkle a bit when buttoned. I also have wonky shoulders from a jiu-jitsu injury a long time ago and that sometimes makes my jackets look off.

Regardless, I still enjoy wearing this jacket, as I feel like it looks much better in person than it does in pictures. I like the fact that this style of jacket is so classic that I will be able to use it forever. I also don’t really mind the imperfections too much. I always write about making sure you aren’t being fastidious with your clothes and to just relax and enjoy them. As you can see, I am walking the walk when it comes to this jacket.

I know that there are some people who don’t like gold buttons on blazers, but I say embrace them! When else can you wear something with ornate, jangly, gold buttons? It adds a sense of whimsy and fun to getting dressed.

In the breast pocket of my jacket, I wore an orange and blue silk pocket square from Men’s Wearhouse. Please excuse the funky lighting in the men’s room of my office.

My shirt was a wide-stripe, blue and white, oxford-cloth-button-down from Brooks Brothers. The collar-roll on this shirt is pretty good. Much better than my Lands’ End oxford shirts, even though I prefer the Lands’ End oxfords overall. Also, the blue/white awning stripes looked a bit summery paired with the orange/blue pocket square and I felt like I should take advantage of the waning days of summer.

Pants were Lands’ End non-iron chinos. These are real workhorse pants. I hardly ever wash them. I simply hang them up at the end of the day and they look perfect for next time. They look a bit rumpled here but this picture was taken hastily at the end of the day before anyone else came into the men’s room and thought I was a screw-ball for taking bathroom selfies.

The chinos are also an excellent middle-of-the-road thickness where I feel like I can wear them in both summer and winter.

Belt was a mid-brown, leather belt from Men’s Wearhouse. I know some people like to get the color of their belt to exactly match their shoes, but that’s a rule you don’t have to follow too closely (I wrote about that one a while back).

Shoes were burgundy Bass Weejuns. Socks were tan to somewhat match the pants.

My watch was a 42mm Bulova on a black leather strap. Don’t bother matching your watch strap to your belt or shoes.

To literally top it all off, I wore a charcoal grey, plaid, wool/cashmere, six-panel, Stetson cap on my commute.

This time of year, the biggest thing I had to consider when deciding what to wear was the temperature fluctuation. The morning was in the 50s, but it got up to mid-70s by the afternoon. What do I wear that will keep me comfortably warm on the train platform at 7:00am, but not so warm that I’m sweating at lunchtime?

The solution was the navy blazer, which is one of my lighter-weight odd jackets, and my cap, which, while thick enough to keep me warm on a cold and rainy day, isn’t so thick that it looks out of place when it’s still technically summer.

Since I work in the city but live in the country, I get the opportunity to authentically dress in ways that span a pretty large spectrum. I will showcase those outfits in the coming weeks.

Have a wonderful weekend!

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