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Buying 2 of These 3 Sports Jackets - Which Would You Suggest?

Al Shosty

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Hi everyone,

I'd written a very long message, but I've deleted it and created a TL;DR. Thank you in advance for your opinions.

Young (early/mid 20s) white man with an olive complexion and (very) dark brown hair looking to buy 2 out of 3 sports jackets to go with navy wool trousers (could very, very occasionally pair with jeans) from around October-May'ish. Living in London. Choices are olive, gray herringbone and gray check. Would either wear them at fun (probably 75% of the time) or semi-formal (i.e. networking, meeting connections 1-on-1) events (probably 25%).

Grey herringbone: https://www.jcrew.com/uk/p/mens_category/sportcoatsandvests/wool/ludlow-classicfit-tweed-patch-and-flappocket-blazer/J3455?color_name=classic-grey-herringbone

Grey check: https://eu.suitsupply.com/en_GB/jackets/havana-grey-check-jacket/C1254.html?cgid=Jackets&prefn1=colorID&prefv1=grey

Olive: https://eu.suitsupply.com/en_GB/jackets/havana-green-jacket/C1258.html?cgid=Jackets&prefn1=colorID&prefv1=green

(a) 2 Greys.
Positives: Good mix of 'formal' & fun, can wear burgundy shoes + black turtleneck (these are other items of interest which I would appreciate being able to wear with these jackets) often.
Negatives: Monochromatic/A bit boring. Gray herringbone might also make gray check redundant, as it is also ok for more fun events, but not sure about this. Would like your opinion.

(b) Herringbone & Olive:
Not enough fun/'pop'. More importantly, I'm not sure what olive is really for in terms of formality/event types, but it looks good on me (+ would open up the possibility of wearing brown shoes), so I'd like to find out (this is probably the main sub-question I have).

(c) Olive & Check:
Nothing formal to go with navy woollen trousers. Could wear check, but very flashy & don't want to come off as a peacock at more serious events (feel free to disagree). And again, don't know when olive would be appropriate/desirable.

Any alternatives would obviously be appreciated.
 

papado

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Green is fine--I would caution away from grey unless you already have a lot of other color sport coats. The grey will work with navy pants, but not much else. Normally I would suggest a blue jacket but as you plan on pairing with navy pants that throws those out of the question--perhaps try something in the brown spectrum? Else I would say you should get some mid gray trousers and get a navy sport coat. Else you could get some olive trousers and wear brown/camel/navy jackets.
 

Al Shosty

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Green is fine--I would caution away from grey unless you already have a lot of other color sport coats. The grey will work with navy pants, but not much else. Normally I would suggest a blue jacket but as you plan on pairing with navy pants that throws those out of the question--perhaps try something in the brown spectrum? Else I would say you should get some mid gray trousers and get a navy sport coat. Else you could get some olive trousers and wear brown/camel/navy jackets.
Hey papado, thanks for the reply! I'm thinking that I need at least 1 gray sports coat to go with navy slacks, and I think the herringbone is more versatile than the check for all kinds of occasions. The question now is: what should my second choice be? I think brown would be an ok choice, but I think that with my complexion it kind of washes me out. I also don't really like the look of it with more formal trousers. I think olive would be a better 'earth-tone' alternative. I've written a separate comment about my thoughts on which jacket should/could come next.It looks like you're really averse to gray sports coats, so I know what your answer is going to be!
 

Al Shosty

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Hey everyone,

After thinking about it a little longer, I think a gray herringbone is definitely in the top 2. The question is: what should come next?

The grey check would definitely work better with navy slacks, look good/make a statement on a night out etc, and would generally just pop out in a way that would look pretty cool. The negative is that by the time I get to this, I'll have already purchased a double-breasted navy blazer to go with my mid-gray and charcoal slacks, which would already be a very daring statement. I like the symmetry of having 1 serious & 1 formal blazer for each trouser 'family' (grey & blue), but I'm just concerned that I won't want to be making that many statements that often, and that ultimately I would just look really monochromatic and predictable for the majority of the year whenever I want to dress up.

The olive would definitely add a new dimension to my wardrobe, but I'm not really sure what that dimension would be. I have this pair of navy chinos that I usually only wear in the spring/early fall, but I could wear it with them + brown shoes for a more relaxed look. I guess I could also wear it with jeans, though I don't know how sold I am on that look. I just don't know what I would wear it to .... a lunch date? going to the movies? A walk in the park?! On the other hand, it would definitely break up the grey/navy/burgundy/black monotony that I've got going on right now. It's kinda feeling like a (fun) prison, and this would definitely add a splash of colour to it.

My head says check, but my heart says olive. What do you guys think?
 

papado

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Hey papado, thanks for the reply! I'm thinking that I need at least 1 gray sports coat to go with navy slacks, and I think the herringbone is more versatile than the check for all kinds of occasions. The question now is: what should my second choice be? I think brown would be an ok choice, but I think that with my complexion it kind of washes me out. I also don't really like the look of it with more formal trousers. I think olive would be a better 'earth-tone' alternative. I've written a separate comment about my thoughts on which jacket should/could come next.It looks like you're really averse to gray sports coats, so I know what your answer is going to be!
I own a grey check sport coat (more of a grey/blue/taupe combination check) so I have nothing against them per se but if you're asking generally I wouldn't say it's the most versatile color for dressier situations. My current collection is: grey check, brown and pink check, camel with navy windowpane, navy with shadow check, rose with blue overcheck (unlined for spring/summer only!).

As you can tell by my listed coats i have a thing for check/windowpane patterns :) so if I were you I would actually opt for the grey check and the olive so you have some choices; You don't need 2 gray jackets. Personally I like jackets with a pattern and keeping pants/shirt more basic and solid. If you prefer the solid jackets (which you're saying you do like the herringbone) then get the olive one next.
 

Al Shosty

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I own a grey check sport coat (more of a grey/blue/taupe combination check) so I have nothing against them per se but if you're asking generally I wouldn't say it's the most versatile color for dressier situations. My current collection is: grey check, brown and pink check, camel with navy windowpane, navy with shadow check, rose with blue overcheck (unlined for spring/summer only!).

As you can tell by my listed coats i have a thing for check/windowpane patterns :) so if I were you I would actually opt for the grey check and the olive so you have some choices; You don't need 2 gray jackets. Personally I like jackets with a pattern and keeping pants/shirt more basic and solid. If you prefer the solid jackets (which you're saying you do like the herringbone) then get the olive one next.
Thanks for the detailed response! I think you're right - what's the point of having two grey jackets? I likes the Herringbone, but when I tried it on I still got the sensation that I was wearing some kind of uniform. I think the grey check will definitely assuage those concerns.

I think I'll get the check now and the olive in late 2019. My 3 cold-weather SJs would then be:
(1) Navy - to wear to any kind of event at all, but especially to more formal ones
(2) Gray Check - Fun nighttime blazer with navy trousers/chinos AND fun daytime blazer with jeans
(3) Olive SJ - Strictly with jeans during more casual (esp daytime) events (movies, lunch date, going to a musical here in London).

As my fourth and final one (I don't know when this would be) I'm thinking of getting a DB navy blazer when I really want to make a statement. I'd probably be choosing between this and the Gray check on a night out. While the Gray check is more fun, i think that if you really have the cojones , you could wear this to slightly more formal events than you would the check.
 

Al Shosty

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Thanks for the detailed response! I think you're right - what's the point of having two grey jackets? I like the Herringbone, but when I tried it on I still got the sensation that I was wearing some kind of uniform. I think the grey check will definitely assuage those concerns.

I think I'll get the check now and the olive in late 2019. My 3 cold-weather SJs would then be:
(1) Navy - to wear to any kind of event at all, but especially to more formal ones
(2) Gray Check - Fun nighttime blazer with navy trousers/chinos AND fun daytime blazer with jeans
(3) Olive SJ - Strictly with jeans during more casual (esp daytime) events (movies, lunch date, going to a musical here in London).

As my fourth and final one (I don't know when this would be) I'm thinking of getting a DB navy blazer when I really want to make a statement. I'd probably be choosing between this and the Gray check on a night out. While the Gray check is more fun, i think that if you really have the cojones , you could wear this to slightly more formal events than you would the check.
 

Al Shosty

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I don’t like grey jackets cause they don’t pair with grey pants easily, but if you are really keen on getting one, this looks better:

View attachment 1091588

https://apac.suitsupply.com/en/jackets/havana-grey-check-jacket/C1261I.html?cgid=Jackets
Thank you for this alternative, I agree that it's probably a bit better. What would you say about this one though? I think this is the best of them all:

https://eu.suitsupply.com/en_GB/jackets/havana-grey-check-jacket/C1061.html?cgid=Jackets&prefn1=colorID&prefv1=grey

I think it could also work nicely with a black turtleneck underneath it too (with navy trousers or chinos and black chelsea boots), potentially giving me 2 different looks depending on the occasion (maybe /w a turtleneck for dinner vs without one for bars etc).

It's distinctive whilst retaining an almost menacing quality which I really like.
 

Al Shosty

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Honestly, I think these two jackets just represent different types of events - the gray check would be a statement on a night out/informal dinner/evening date, whereas the olive would mostly be worn during the day and/or in casual-yet-not-too-casual settings (lunch/movies/etc). I just have to decide which of those 2 types of events are going to be more common during the next year of my life, and decide accordingly.
 

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