Your fit looks good here.

The color saturation of the seersucker is really low and it reads as nearly white. So you’ve got a lot of leeway when picking colors. I would just steer away from near matching colors and patterns.

To me, colors that almost but don’t quite match are the worst. A real pet peeve that drives me nuts.

I like it. It looks composed and thoughtful. It’s still got some flashy style like the other one you posted, but more intentional.

They might be what’s called “commuter” gear. It’s performance gear that you can wear off the bike. The combination of hi-vis accents, zippered pocket, and chino cut makes it sound like it could be.

Short answer is yes, it’s too Jokerish.

Longer answer is still yes, but how to fix it depends on how Joker adjacent you want to be. Feel free to dress however you want. You can pull off a lot of looks by being confident and comfortable in your outfit. But since you’re asking I’ll share a couple of thoughts about what I would do. Feel free to mix and match based on what you prefer.

Change the black shirt for something else. Something lighter, maybe a lavender if you want to have a purple theme. Your shirt should be the lightest part of your outfit and it shouldn’t match your pants this close. If you really want to keep a dark shirt look, check out pictures of Regis Philbin when he was hosting Who Wants to be a Millionaire. It’s not a look I personally like, but he pulled it off pretty well.

Add a blazer or sport coat, and lose the vest. Vests are hard to do in anything other than a very formal setting. If you want to keep the vest, at least move the pocket square to the blazer.

Change the pants to something like a charcoal grey. Dark grey is much easier to wear than straight black and I promise it’ll look way better with your shoes.

Change the tie or pocket square, they shouldn’t match this much. One of the hard parts of dressing in monochrome is that it makes the color you do use really stand out. For the square, look for something that has purple (or whatever colors you’re focusing on) in it. For the tie, maybe try a black tie. If you want to have solid color (that’s not black) tie, think about trying out a knit tie. I’ve got a black grenadine tie that is really easy to wear with a lot of different outfits.

Lose at least one piece of jewelry accessories. There’s too much going on in too little space. You can still wear some other pieces elsewhere, like a bracelet(s) or ring(s) but don’t go nuts with it.

I wear Gustin’s, but I get your problem with the low rise. If you’ve still got them check if they’re slim, skinny, or straight fit. The straight fit is still kind of low, but the slim is really low (I have not tried on their skinny fit). They also vary a bit on each model. I’ve sent back a couple that had the same measurements but simply didn’t fit right.

If we count specialized shoes, then I think it’s about a 15 pairs. That does include a pair of waterproof felt-soled fly fishing boots, waterproof and insulated muck boots, safety-toed boots, Olympic weightlifting shoes, motorcycle boots, and slippers.

For regular wear I’ve just got two pairs of brown leather dress shoes, one black pair, one pair of chukkas, and two pairs of sneakers. Then I’ve got a handful of other shoes that I thought I’d like more than I did. Some day I’ll eBay all that stuff.

There’s stuff out there, but it is harder to find. It’s going to be especially hard to find right now. If you want more colorful clothes look again when the Spring and Summer looks come out. The Winter styles are going to be more muted and less colorful.

I like Bonobos and Todd Snyder for when I want something more interesting. Although Todd Snyder is definitely caught in the muted colors for winter thing.

I’m not real familiar with the style, but you might have some luck searching around for “techwear” and “technical workwear”. Those pants remind me of stuff I’ve seen in that realm.

A quick search turns up the company Truewerk and they have some that look similar and have the extra pockets and similar details.

Clark chukkas are one of my go to nice, and casual shoes (boots). The Clark’s are great value for the money too. I like their Wallabees too, but those tend to be pricier and are a less universal style.

A clean pair of Adidas Stan Smiths can look good too. Really any of the simple sneakers will look good with most outfits, like these, the Nike Cortez, or whatever. I don’t like sneakers that look too technical or chunky, but that’s just me.

Johnston and Murphy has a mixed reputation and are expensive, but I’ve liked the two pairs I’ve had from them. They’ve been worth their price too, the last pair I had from them lasted about 8 years.

It’s not wrong, but I don’t know how helpful it is. I think it could be helpful for identifying complimentary colors, but it’s missing some context about which articles of clothing are which colors.

For example, it lists pink as a matching color for light blue. IMO, light blue pants with a pink shirt works fine, but a light blue shirt wouldn’t work so well with pink pants. In general you’d want your pants a darker color or cooler tone than your shirt.

Mostly settled. I make the occasional purchase to replace something that’s worn out or to fill in a seasonal gap, and when I do I try to be a little experimental.

I wear classic jacket and tie stuff for work and American workwear when I’m home.

I was unaware of this community until this post, I joined shortly after.

I feel like it’s always kind of a niche topic. Too many people see one style or another as something to be derided for being exclusive and/or unnecessary. Whether its calling suits classist or streetwear drops wasteful. Not too many people are interested in fashion in general, especially men’s fashion.