Wearing boots with shorts
Hi everyone,
What are some of the things you think about when styling boots with shorts? I feel like often when I try it, it doesn’t seem quite right. I suspect the issue is that my boots/shorts are a little dressy/not enough of a military influence for the look, but I was wondering what your opinion is. Here’s a pic of me trying. Feel free to critique what I’m wearing but I’m also hoping for a more general discussion for people trying the look in the future.

19 Replies
(I did do a search for “boots shorts” in QnA, so apologies if y’all have already had this discussion.)
I think you've nailed it pretty much here with the boots in the example being a little too formal/dressy for the outfit
I think it can work with hikers if you lean in, I agree those boots in your pic are a bit too dressy for shorts

If I'm looking for outfits with boots and shorts I'm usually looking at some heckle outfits


Yeah, boots with shorts work pretty well in a hiking context imo
Got it, so less formal boots would work better. Do you think the opposite is also true: that a more formal rest of the outfit would also integrate them? Or do only less formal boots work for you?
and actually I'm noticing an immediate difference in the examples above and yours is the type of sock as well
Oh yes I was also wondering about that
the above examples are using a chunkier more sports/hiking sock which I think adds to it looking more casual
propably no tbh. Its less of a formality thing than a vibes thing imo.
personally for me I'm not sure about a more formal outfit because it's not something I wear so don't really feel like I have the experience for that
Yeah totally agree about the hikers
Like formal shorts? Maybe if you're tryna be Thom Browne but that's high skill territory
Maybe if you were to heavily lean into more avant-garde stuff I guess
lol ill wait a bit to work up to that
sal my boot w short goat




imo ur fit needs some edge or some crunch to it for this to work really well
Totally, first person to come to mind for me as well
Different socks but it’s possible… I almost wore boots and shorts today but it’s not as easy