Basic Bastard First Brown Leather Footwear Advice
I am looking to buy my first brown leather footwear.
The guide (https://malefashionadvice.substack.com/p/building-a-basic-wardrobe-v70) suggests Clarks Desert Boots / Chukka, Derbies/Bluchers (possible preference for round toed suede in 2023), Chelsea Boots, Blucher Mocs, or Service boots.
The updated 2023 guide (https://imgur.com/Xvv3AO4) suggests lace up/service boots.
I already have stan smiths and some older black oxfords - my ideal setup is the stan smiths for generally going out / parties, black oxfords for formal, and the brown leather I will be buying is for MAINLY business casual / dates, but I would like them to ideally be as versatile as possible without sacrificing on the business casual.
I have done hours worth of reading and I have come to the conclusion that there isn't really a consensus.
My main confusion is on whether to get a single pair of nicer more expensive service boots, (Allen Edmonds Higigns Mill Brown Chromexcel Leather, or Grant Stone Diesel Crimson CXL or Earth Waxed commander).
OR
To have 2 cheaper more specialized boots/shoes for the same total price, such as one Chukka (Clarks Desert Boot Beeswax) and/or one Chelsea (Canada West Romeo 14337, Blundstone, or a different dressier one), and/or one service (Canada West WM. Moorby 2801, Iron Ranger Blacksmith) and/or one derby shoe or blucher moc (I have no idea what to choose for shoes).
Again, my main concern is having something nicer than sneakers to wear for dates, business casual, stage presentations, etc.
I live in Canada and so I am leaning more towards boots, but I am not sure what is ideal for my situation. I am in my mid 20s if that changes anything.
My budget depends on how much use I can get out of it. For something I will wear at least twice a weak and will last years, I could spend up to around 500 USD.
32 Replies
Honestly I think you're just thinking way too hard about this. at some point ya gotta make a choice and send it. if it were me, I probably would not buy two different variants of the same kind of shoe (1 chelsea and 1 chukka as an example, both boots, can fill similar purposes in an outfit). but even that's just me, I'm not that boot obsessed. and the decision of whether to buy like 1 boot and 1 loafer/moc/etc or 1 much nicer boot, for sure there's no objectively correct path there. all of what you have listed will work just fine in the contexts you're aiming for.
if you're struggling with the decision, look for inspo with the types of shoes you're eyeing and see if that inspires any choices. if you truly cannot make any commitment, roll a die.
i have been in the same place as u eletheheroic, and i spent a lot of time thinking about the boots i wanted only to buy them and wear them for a week and hate them
that all said, I'd suggest on just buying the 1 brown boot you like and going with it
There is also the question of is this solely for events/dressier occasions or will this also have to fulfill a lifestyle use as well. But in general I would start with only one pair of whatever and see if you even like wearing them. Also sizing is psychotic for everything so don’t be surprised if it takes some work to find a shoe/boot that fits and is the right size
Any first purchase is tough cause once you have something in your rotation, you’re gonna discover what you like and don’t like, and you’ll have to iterate.
And that’s personal, not something a guide can tell you
I’m not gonna lie, if it’s your first time wearing nicer shoes, I’d go with a cheaper brand in a color you like because you might end up not enjoying the style you think you’d like. Then in the future, you can upgrade to a higher quality version because you’ll have a better understanding of your taste
If possible try stuff on in person to
I’ve bought so many brown leather shoes that I never wear because it doesn’t work with my personal style that I wish I tried them out with cheaper brands first
Do you want brown boots because you like them or because the basic bastard guide says so?
It will ideally be lifestyle / events, something I can wear to the office AND dates, and not feel bad about taking them out if need be. I am personally leaning towards service boots but I have been told most of them are a bit too work boot like, hence the mill brown / diesel - but I don't know if a cheap chelsea is better for dates / office anyways.
that's also a good question raisin
any shoe is a date shoe, so don't think about that 1 so much
That's a fair question. I think my main concern is that I genuinely don't have any business casual footwear at the moment, and I am stuck between my formal oxfords and my sneakers (though I do get sneakers can be worn for dates). I like the look of brown leather, and boots seem more general purpose especially for the winter.
Boots in winter can be an iffy thing unless you maintain upkeep on them. I’m assuming since your in canada land they do something to maintain roads and that shit can wreck leather if you don’t maintain it
I think it is also the case that the cheaper service boots are less dressy, so I'm thinking if I buy a cheaper service boot it will kind of just be a waste
if there's a lot of ice and snow where you're at in winter then vibram soles would be nice
If the roads/sidewalks are clear I wouldn't worry about winter specifically
I have a separate pair of winter boots, light snow and some wetness is what I would need for the leather
Depends on the vibram tbh, lug soles you want the special fire and ice ones, wedge soles is whatever
Yeah I wouldn't be too concerned then
agreed
I wear my docs in that kind of weather and they are absolutely not winter boots lol
thirded
Dress boots and service boots are at different ends of the spectrum, service is military/work while dress is dress. If you want a dress boot nothing wrong with that but you’re going to have to look more towards those styles
I don't think dress boots even need to be in the convo given op's descriptions so far lol
I don't need it to be too dressy but I would like it to feel in place in business casual and professional setting.
that'll include most any kind of boot that isn't super directional
I think it would be helpful to simplify the discussion and not introduce more variables and more confusion
My question is more like, if there was any one (or 2) brown leather footwear I should get that fits between my white sneakers and my black oxfords, which should it be? Stage/conference presentations and dates and business casual. Chelseas and chukkas are I guess more fashionable and chelseas more formal, service boots are more general use, and I guess I thought that a more expensive service boot like the diesels would be the best of both (and some reddit threads suggested they are better for business casual than a cheap chukka).
all of the boots you listed in the original post will work in the contexts you're aiming for, and probably even some that you aren't too. I think char's advice is particularly apt, start cheaper (2nd hand also a good option for this), try the shoe/boot style that appeals to you most out, see how it feels after a while of wearing it. you'll come away either real lucky with a shoe you love, or with some things you like and some you don't, and it'll inform your next pickup if you need one.
if we tell you which shoe to get, you will be buying someone else's favorite shoe, not yours
I think ur in the browsing stage
by that I mean, go on some of the big boot brands websites, look at some models you like, and come back for more info
Its hard to have this convo without pics or any idea of what you might want
Thanks for the advice all. I think part of it is I don't have that much sense of personal style yet, or what is more/less formal. My shortlist going into this was these 4 - the CW Romeo chelseas, the GS diesels, and the CDB, CW WM Moorbys. For pictures, which of these is the most formal/dressy?
most would prob say the GS are the most dressy
but outside of wearing with like, a suit, the other 3 would all work in similar contexts
That's perfect, my issue is that the other 3 are like half the price lol, but it does make my choice easier thank you
Personally I'd say get the desert boots and see if you actually get any use out of brown boots. Maybe you won't wear them much at all, or decide you'd prefer a derby or a loafer. You won't be out too much money with desert boots. If you wear them a lot and want something similar but different you might have more of an idea what that is by that point.