What type of footwear for a date?
Background: late 30s male living in Canada. Budget: $300-400 CAD (max).
I'm looking for some footwear that I could wear on a date to a restaurant, or an art gallery or museum, or something that is a little bit more formal than just a walk in the park. Something that could be paired with chinos and a tucked in shirt, with MAYBE a blazer on top of it (but probably not). I'm not talking about dress shoes that would go with a tie as I'm not aiming for that level of formality - I just want "the next step up" from sneakers so I don't look too casual. Would also like to be able to wear this footwear when out and about and trying to be a bit more classy than sneakers too.
I'd REALLY like to be able to "try before I buy" or at least have free (or very affordable return) returns: I prioritize comfort in whatever I wear as I know if it feels uncomfortable I'll be looking for reasons to avoid it.
I looked at the guides for footwear but was overwhelmed with the options.
41 Replies
I mean I would maybe say a pair of loafers
loafers or derbies probably yeah
boots also work
and trying on depends where you are, if you are near a major city its a good chance you can try some on
because fashion is fluid we’re at a point where “more formal than sneakers but not so formal you’d not wear them with a tie” doesn’t really exist outside of maybe driving loafers and those aren’t great
there are threads in here for all types of stores or just ask people know where near you could be good to try stuff on
Thanks! I was looking at "Captain" boots from Thursday Boot Company - I'm aware they're not the highest quality, but they're in my price range. Would those be fine, or are they too "workboot" style?
the style is fine but id go for something else over Thursday if you find something else in your price range you like
I agree with kyn there is better option in that price range
Meermin maybe
my first thought was grant stone but it would have to be on sale or B grades
the edward is one i find do be a nice dress-ish boot
or something in that style
I saw Grant Stone and a few other options but they don't do free returns in Canada
Thursday has free returns via Amazon which is convenient which is why I started there
if it matters to you, the people who founded/run Thursday are pro-Trump/anti-abortion so I personally won’t recommend them
If you can find a pair you like in your budget, red wing is a good option, grant stone/solovair/meermin are also good tho higher variance depending on what you buy
It's really the return cost that is stopping me from trying those brands. The boots would be at the top/beyond my price range so they'd need to be a perfect fit and I probably can't do that without at least one return, which would be too costly.
I will say grant stone sizing is crazy well documented, If you go to a shoe store and get a bannock mesurment they are going to fit as good as they can without a custom last.
but i do get the fear
are you sure no where near you stocks brands like GS or redwing?
GS is online only
Yeah there’s a wealth of information for sizing for these brands out there
S&S has it but they might be special
What is S&S?
standard and strange
Hmm do they have a lot in stock?
I might be doing a roadtrip to Boston-NYC area soon and could potentially stop in for an hour or two somewhere
the odds that you cannot find find an article of clothing nyc is effectively zero with a little planning
looks like they dont right now, but they know thier stuff with sizing im sure they would be able to help get you a good size online.
but i think theres somewhere else in nyc that has them
if that roadtrip happens to be like october 8th then bootcamp is happening so your for sure set lol
What is bootcamp?!
its a heritage boot/ leather footwear... event
idk what to call it but lots of makers and people into boots
ah i found it: https://www.stitchdownbootcamp.com/
Stitchdown's Boot Camp: Oct 12-13, NYC
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yeah
oh i got the date a tad wrong
Hmm I wonder if I could make it work
That weekend is Canadian Thanksgiving 😭
Alright thanks guys, I'm going to see what I can do. Looks like a pair of dress-ish boots or the equivalent in shoes are the answer here.
yeah for sure! good luck my only other tip is try and get your feet mesured with one of these then most boots tend to be half a size down from that.
will save a lot of headache on returns if you go off sneaker size
Thanks. I'm an 11D on it.
Left foot 10.5D right foot 11D :letsfuckinggo:
so probably go with a 10.5 D to start in most boots
I bought pairs of Thursday captain boots in size 10/10.5/11 (D) before making this post, so it'll be a good reference
free returns
oh sorry I have one more related question
Is buying leather boots/shoes used a good idea? Or is the foot wear pattern in the sole from the first owner going to mess it all up?
I’ve never had an issue with used footware myself but you can always get the sole replaced (like if they’re good boots that you wanna keep you’ll do this anyways
As for new - if you can go to a red wings store their boots are COMFY
Iron Ranger | RedWing
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I’m very big on comfortable footwear, if your feet are unhappy you’re unhappy.
I wear their work boots casually just because they’re comfy AF
Thanks
I need comfort as well (non-negotiable), but I'm looking for something on the dressier side, trying to stay away from workwear styles
You could try Canada West Boots, they have some styles in this category (particularly the WM Moorby stuff). Their website has a pretty comprehensive list of retailers.
If it were me though I’d try to find a pair of derbies.
You could try browsing what you see on larger retailers with free returns (like SSENSE) and post examples of what you like here, or in a new thread and we can try to give advice based on that
https://www.ssense.com/en-ca/men/sale/lace-ups-oxfords?sort=price-asc
I love buying used footwear. Especially quality brands like Alden. If you know your size it’s a great way to get good shoes for much cheaper than retail.
I have had no issue with used boots, and price falls off pretty heavy on them so you can get some great deals