Outfit Of The Week 12/10/23 – 12/16/23

This week definitely brought some unexpected wintery weather! We definitely didn’t anticipate the snow. It sure is beautiful, though!

This week’s edition of “OOTW” highlights an outfit I wore to an event at my sons’ school. It was a community holiday event and I wanted to dress up a little without compromising my comfort in the cold and snowy weather.

The centerpiece of my outfit was my tried-and-true Harris Tweed, herringbone tweed jacket from Brooks Brothers.

What I love about this jacket (and tweed jackets in general) is that since they are jackets they are inherently dressier than NOT wearing one, but they are so casual and rugged looking that you don’t look out of place even at a very casual setting. In my opinion, tweed jackets achieve what all those other “casual sport coats” are trying to achieve: looking put-together but not stodgy.

The pocket square was a brown, green, blue, and yellow cotton plaid from Charles Tyrwhitt. I find this dark square provides some good contrast with the light grey of the jacket.

Under my jacket was my burgundy, cashmere, v-neck sweater from Lands’ End and a light blue, oxford-cloth button-down shirt from Charles Tyrwhitt. This OCBD isn’t one of my favorites. The cloth is a bit stiff and the collar points are way too short. It’s a good knock-around shirt, though, considering how inexpensive it was. CT is always doing crazy sales, so NEVER buy their shirts (or anything of theirs) at full price.

My watch was my 42mm, silver dial Bulova on a black leather strap.

My chinos were also from Lands’ End. The boots I chose were my L.L. Bean work boots.

Again, this was a casual event and there are a few inches of snow on the ground. I knew if I wore a nicer pair of proper shoes, there was a chance my ankles would get wet. In order to preserve my overall comfort, I needed to lean towards more utilitarian footwear.

For my outerwear, I could have donned a more formal overcoat and hat, but given the fact that this was a very casual event, I didn’t feel those were appropriate. Instead, I went with my L.L. Bean barn coat. I wasn’t trying to look all “super trad”, it’s just the only other winter coat I have, other than my overcoat, that fits over a tweed jacket.

To top things off, I wore my brown, herringbone, newsboy cap from J.J. Hat Center.

I think what I liked so much about this particular outfit was how versatile it was. It’s not super formal so it didn’t draw the dreaded “Why are you so dressed up?” comments, but it’s just formal enough to look put-together. Also, since the outfit consisted of a tweed jacket and machine-washable pants, I didn’t feel precious about wearing it around the house to play with the kids or cook dinner. Lastly, the layers meant I could strip down a little and roll my sleeves up to get some dishes done without feeling the need to change.

The real key to looking stylish is whether or not you feel comfortable in your clothes. The only way that’s going to happen is if you actually WEAR them. They might get dirty. They might get stained. That’s ok. I’d rather wear something and ruin it than have it hanging pristinely in my closet because I never wear it.

Have a wonderful weekend!

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