Outfit Of The Week 5/4/25 – 5/10/25

Man! The past week has been really weird, weather-wise. It’s been raining torrentially for like five straight days.

Why is it that whenever it rains someone ALWAYS says, “Well, we needed it.”?

I live in the Northeast. It rains regularly. It’s not like I live in the desert or in a place prone to wildfires. And the ground is already saturated from the melted snow. So, did we really need the rain?

Anyway.

This week’s edition of “OOTW” is a casual left-turn from last week’s conservative formality.

The highlight of the outfit is the leather biker jacket.

Readers of this site will remember that I wore this jacket much more frequently this past autumn than I had in years prior. It’s such a cool piece and only feels more and more comfortable the more I wear it that I wanted to give it as much use as I could before the fall weather turned too cold.

Today’s outfit marks the jacket’s first appearance this spring.

Interestingly, I usually wear this jacket more as the weather trends from warm to cold rather than the other way around. I am not sure why. I think it may be that it feels like an affectation if I’m wearing a leather jacket if the day turns unexpectedly warm.

Since the jacket is eye-catching, I always try to make sure I’m wearing it in weather-appropriate situations. Like I’ve said before, authenticity is important in what we choose to wear and wearing a biker jacket, even with all its coolness, isn’t terribly authentic if it’s hot out (considering I don’t actually ride a motorcycle).

Even though this jacket is very casual, I still need to be particular about how I style it. A leather jacket calls for boots, obviously, and I chose to wear my Carolina loggers. I also wore jeans and flannel shirt, which always look good alongside leather.

I decided to tuck in my shirt mostly because the jacket is waist-length. If a shirt is untucked, sometimes the bit of fabric that falls below the bottom of the jacket can look unsightly and draw attention to the hip area (which is NOT ideal). If your shirt, pants, and jacket are all dark colored, then the effect isn’t too profound. However, I still think it looks better to have a tucked-in shirt when wearing a waist-length jacket.

Whenever an outfit consists of multiple leather items like a jacket, belt, and boots, there is always the question of whether one should “match leathers”.

Personally, when an outfit is casual, I don’t stick to that “rule”. There’s nothing wrong with matching your leathers, as in making sure you wear a black belt and black boots with your black leather jacket, but sometimes that can feel a little too fussy to me.

And a casual outfit should be anything but fussy.

Now, would this outfit have looked better if my belt and boots were black? Maybe. But my black boots aren’t nearly as comfortable (or practical) as the ones I wore here, so I didn’t want to sacrifice comfort/utility for fashion.

When it comes to headwear, I find my options are a bit limited when wearing this jacket. If I am wearing my Barbour or my Harrington, for instance, I can wear a newsboy cap, or a baseball cap, or a wide-brimmed Stetson. Anything, really.

With this jacket, I find that the hats that work the best are a wool watch hat (beanie) and the sleek, charcoal grey, wool cap you see here.

My regular, brown, newsboy cap is a little too “country”, in my opinion, to look good with the more urban-leaning feel of the biker jacket. Same goes for the Stetson.

I’m really loving how the jacket is conforming to my body. When I first got it a few years ago, it was quite stiff when I raised my arms out in front of me, partially due to the lack of gussets on the back of the shoulders (often seen in “action-back” jackets), which allow more freedom of movement (like when extending the arms to grip motorcycle handlebars).

After a few years, and especially after wearing it so much last year, the leather is stretching out in all the right places.

From a practical perspective, I love all the zippered pockets (which are perfect for stashing the kids’ toys or extra snacks). Also, the tall collar keeps out all the elements, which was especially helpful on this particular day.

A lot of men refrain from wearing cool stuff like this jacket because they think they could never “pull it off”. They’re worried they would look or feel silly or that wearing the jacket would garner comments from the peanut gallery.

All of that might be true. But I always say that I would rather be the bold dad in the leather jacket than the timid dad in the hoodie. I would rather be noticed for my kickass jacket than not be remembered at all.

Whenever you wear something cool like this, people look at you and secretly wish they could do the same. So, wear the cool stuff. Be someone else’s source of confidence.

Have a wonderful weekend!