Finding my place on the sartorial spectrum

[malligator]

Well, for what it is worth, that is a good start. I like the jacket and it goes with both the jeans and the boots. Not knowing where you live, and what kind of climate you endure, it is hard to suggest what to look for.
For warmer weather I would suggest a linen jacket, perhaps like the one you have in style, but in linen. Or for colder weather a jacket in tweed, check, herringbone or whatever style you prefer. You can stay with jeans, unless it is very warm then chinos work better. As has been suggested elsewhere, add gradually and build up your wardrobe over time. Ebay is a good place to begin with until you really know what you like, selling on stuff that you are not happy with.
There now, a deck ornament has given advice to an inhabitant of the greasy grotto.

Thanks, Chouan. I live in Seattle. I'm not sure how warm it gets here yet. I've been assured that it does, indeed, get hot, but having moved here from Phoenix I'll have to wait and see. I went to Nordstrom this weekend (I really need to figure out other places to shop) looking for warm weather jackets. They had a lot of unlined jackets, but no linen, seersucker, or fresco jackets made specifically for warm weather.

I love tailored tuesdays. Mind if I borrow that for the hashtaggery prevalent on social media?

Absolutely. I'll start looking for it.

 

[Chouan]

Thanks, Chouan. I live in Seattle. I'm not sure how warm it gets here yet. I've been assured that it does, indeed, get hot, but having moved here from Phoenix I'll have to wait and see. I went to Nordstrom this weekend (I really need to figure out other places to shop) looking for warm weather jackets. They had a lot of unlined jackets, but no linen, seersucker, or fresco jackets made specifically for warm weather.



Absolutely. I'll start looking for it.

On-line might be a good place to look. As long as you know what your size is. I don't know much about US makes I'm afraid.
Seattle is, I would imagine, not as warm in summer as Phoenix, and will be a lot more humid as well, I would think. I've only been there in winter, when it was quite cold and very wet.

 

[rajesh06]

On-line might be a good place to look. As long as you know what your size is. I don't know much about US makes I'm afraid.
Seattle is, I would imagine, not as warm in summer as Phoenix, and will be a lot more humid as well, I would think. I've only been there is winter, when it was quite cold and very wet.

Seattle can get very warm - but not hot and is not humid. You should note that a significant percentage of homes in Seattle are not air-conditioned.

 

[rajesh06]

On-line might be a good place to look. As long as you know what your size is. I don't know much about US makes I'm afraid.
Seattle is, I would imagine, not as warm in summer as Phoenix, and will be a lot more humid as well, I would think. I've only been there is winter, when it was quite cold and very wet.

Have you thought about going to Mario's and hooking up with a stylist to help you through your journey?

These days, places like Mario's are a rarety. You are fortunate to have access to one locally. Skip the internet and take advantage of that.

 

[jaxenro]

Two men can wear an identical uniform one looks good in it the other not. Why?

Fit. Try making sure the items you wear fit you properly. Too long pants, baggy or too tight coats, can make the best most expensive suit look like a cheap suit

Look at pictures of a black tie event sometime why do some men look good in the tux better than others? Because it fits them and they have taken the time to make sure the details are cleaned pressed or polished as need be

It doesn’t need to be different and men actually look good in uniforms if the uniforms are fitted well

 

[Chouan]

Two men can wear an identical uniform one looks good in it the other not. Why?

Fit. Try making sure the items you wear fit you properly. Too long pants, baggy or too tight coats, can make the best most expensive suit look like a cheap suit

Look at pictures of a black tie event sometime why do some men look good in the tux better than others? Because it fits them and they have taken the time to make sure the details are cleaned pressed or polished as need be

It doesn’t need to be different and men actually look good in uniforms if the uniforms are fitted well

I always looked good in mine.....

 

[jaxenro]

My point being people often focus on everything but fit. A day glow orange dinner jacket can fit well and still look trashy but for the most part you can stand out in a crowd in a subtle manner if you wear the same sort of clothes as everyone else if they fit better the creases are pressed etc

 

[malligator]

Although I know I have holes in every aspect of my wardrobe I'm continuing to focus on footwear. Mainly because its my weakest area right now (wearing one pair of leather desert boots every day in Seattle rain is getting nasty), but also because I really like buying shoes. In addition to the longwings I mentioned in my OP I added a pair of dark brown dress boots with commando soles for rainy days. I also bought a pair of very nice wool dress socks.

Now I have two pairs of nice shoes to go with the outfit pictured in the OP. I'm now looking to add a pair of chinos as an alternate to the jeans. After that I'm leaning toward either a pair of gray trousers or a casual textured summer sport coat--I'm still trying to decide if the bright navy hopsack blazer goes with the outfit.

Edited to add:

Also, as I'm in agreement with @jaxenro I am looking for a good alterations tailor.