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
oman121
oman1215d ago
I mean I would maybe say a pair of loafers
kyn
kyn5d ago
loafers or derbies probably yeah boots also work
oman121
oman1215d ago
and trying on depends where you are, if you are near a major city its a good chance you can try some on
kyn
kyn5d ago
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
oman121
oman1215d ago
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
hellosir4906
hellosir49065d ago
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?
kyn
kyn5d ago
the style is fine but id go for something else over Thursday if you find something else in your price range you like
oman121
oman1215d ago
I agree with kyn there is better option in that price range
kyn
kyn5d ago
Meermin maybe
oman121
oman1215d ago
my first thought was grant stone but it would have to be on sale or B grades
oman121
oman1215d ago
the edward is one i find do be a nice dress-ish boot
No description
oman121
oman1215d ago
or something in that style
hellosir4906
hellosir49065d ago
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
kyn
kyn5d ago
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
hellosir4906
hellosir49065d ago
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.
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