Outfit Of The Week 2/23/25 – 3/1/25

This week’s edition of “OOTW” features an outfit I wore for a number of days while we were visiting my in-laws.

I have always enjoyed the simplicity of getting dressed while away from the house. I only had what I packed for the week so I needed to wear the same things over and over again. Some people might hate that, but I find it fun. It forces me to wear a limited number of items in all scenarios in which I find myself. Because of that, I find I forge stronger connections with my clothes and develop positive associations with them.

The highlight of the outfit is a lovely burgundy sweater my wife bought me for Christmas (from Brooks Brothers). It fills a similar niche as my Travel Sweater, in that it’s thin (so it fits easily in a pack), handsome, and versatile.

But while my Travel Sweater is excellent for transitional weather like during spring, this sweater is a bit better for winter, as it’s slightly heavier. Because of that, it served me well during the week at my in-laws’ house as it was very chilly and windy pretty much every day.

For my shirt, I split my time between two light-blue oxfords. One was from Charles Tyrwhitt and the other was from Lands’ End.

My pants were a pair of navy chinos (also from Lands’ End) that my in-laws gifted me for my birthday last year, which I’ve been enjoying wearing as casually as I can.

My boots were my Carolina loggers.

I frequently popped on a wool overshirt from Filson, which has become my go-to “house shirt” and light jacket over the past few months.

I’ve been thinking a lot lately about the costs of things and how that affects our enjoyment of them.

Since the winter is coming to an end, I have been inundated with the usual promotions for new items from various retailers. Naturally, I take notice of the items that most similarly resemble items that I wear most often, like the OCBDs and chinos I mentioned earlier.

Often, those items are priced well over $100.

Now, maybe it’s just my well-honed frugality talking, but I am perfectly comfortable with my $30 oxfords and chinos. Not only am I comfortable with them, but I actually PREFER them to the idea of getting more expensive, and undoubtedly, higher quality versions.

I’ve written before about how the most important things in your wardrobe are the ones you’ll have for the rest of your life. Things like oxford shirts and chinos don’t make the cut.

I like being able to wear my inexpensive clothes around the house and not worry about them getting worn, soiled, or otherwise damaged. I have rambunctious children and an active lifestyle, but I still like looking good. I also have limited disposable income, like most of you. If I’m allocating funds to clothing, those funds are certainly not going to go to pricey versions of shirts and pants that I can get for much cheaper.

I don’t like feeling precious about my stuff. I don’t like feeling like I need to baby something. That detracts from my overall enjoyment of my clothes.

I enjoy my oxford shirts and chinos BECAUSE they’re inexpensive, not in spite of it.

Now, would I feel differently if I COULD comfortably afford much more expensive versions of these items? Maybe. I also might have a completely different attitude towards not feeling precious about my clothes if I was at a lower economic station. I wrote an article a few years ago wondering if being able to dress well is a product of privilege.

All I know for sure is that where I am in my life NOW means I’m not keen to shell out money for products that, to me, don’t improve all that much the higher up the price ladder you go. Is a $198 oxford shirt really 660% more enjoyable to wear than my $30 version? I bet not.

But I might be 660% more pissed if I spilled olive oil on it.

My point is that you shouldn’t feel like you are somehow less stylish or less style-savvy if you have a wardrobe full of pieces from low-cost retailers. It also doesn’t mean you can’t love your clothes as much.

I love menswear and I don’t own anything super expensive. Pretty much all my items were purchased on-sale and nothing cost more than a few hundred bucks, including my suits and sport coats. I have a stable, predictable style, which means I am easy to shop for, so I also have a bunch of things I received as gifts over the years (like shirts and sweaters), which I use frequently. I also don’t own any bespoke clothing.

The most expensive item I own is my Schott Perfecto leather jacket which was a birthday gift from my wife a number of years ago. It was just south of one-thousand dollars, but it’s an item I will have forever and will pass along to my kids. I’ve worn it so much over the years that I’ve definitely made the purchase worth it, even at this point. That jacket was a once-in-a-lifetime purchase.

So, go forth proudly in your inexpensive, mass-produced, imported clothes! I’ll be happily right there alongside you!

Have a wonderful weekend!