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Which Shade of Brown Chelsea Boots Should I Buy?

Al Shosty

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I'm about to buy my first pair of real dress boots. I've settled on brown chelsea boots, but the exact shade has been eluding me. After going back and forth in my head, I thought I'd ask here.

I have 2 options:
(1) Loake Blenheim: https://www.loake.co.uk/blenheim.html
(2) Meermin Dark Brown Calf: https://www.meermin.es/en/10149810170000ye-17-101498-dark-brown-calf-e-marron.html

I'll be wearing either of them in 3 distinct situations:

(1) With dark denim jeans and thick (often cable-knit) sweaters in navy and olive. This would be about 80% of the time, pretty much when I'm just walking around town minding my own business.

(2) With navy chinos and a (darker) olive sports jacket. This would be about 15% of the time. Nowhere near as often as (1), but I'd almost prioritize (2) over (1) given that this would be one of my go-to outfits for any 'smarter' events (wine bars/going out/musicals/plays etc).

(3) With beige chinos and a navy sports jacket. This would be the last 5%, though this would mainly be on rainy spring days, and I'm not sure how many of these there are going to be in my area.

On one hand, I think the loakes are definitely a more ... interesting colour, and would probably go better with (3). I think they're a tie when it comes to (1).However, I think the meermins are ultimately more versatile, and would match with (2) very well, whereas I think the loakes would bomb that.

I'm leaning towards the meermins. What do you guys think?
 

notdos

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Your overthinking it. Brown Chelsea’s in a medium or dark brown calf will work for each of those. Wear and enjoy.

Phillip :)
 

Al Shosty

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Your overthinking it. Brown Chelsea’s in a medium or dark brown calf will work for each of those. Wear and enjoy.

Phillip :)
I think this is exactly what I needed to hear. I overthink a lot of (style-related and otherwise) things in my life, and I definitely think that that's the case here too. Thanks for the reply!
 

Basquash

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I think a dark shade would work better in 1 and 2.
 

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