Shorts + Boots

I've always loved the shorts + boots look, as long as it's done right.  It could be tricky...I don't think I would wear heeled boots with shorts, except for booties (duh).  I find that I often like the look better when it is more of a casual look.  See below outfit from Sunday, and excuse the background.  Oh, and I actually added the socks and belt, but now looking at the pictures, I like the look better without the socks and belt:

See the details of the shirt, love the pattern.

And the dorky glasses for good measure:

silk shirt: thrifted ($4)

gray cardigan: F21 ($16)

green shorts: H&M ($6- sale)

steve madden boots: ($40- gift card + coupon, originally $80)

socks: Ross ($2)

belt: thrifted ($2)

But isn't wearing shorts and boots almost the same as a skirt and boots?
I guess it depends on how you put it together, but I just don't think tall heeled boots with shorts are very cute -again, unless its booties or a little higher than ankle boots.  But, maybe I am wrong and someone out there can pull it off nicely.  I guess dress shorts with tights and heeled boots might work depending on how you really pull it off, and they aren't tall boots.  But I think this is cuter:

 Imagine those are khaki trouser shorts like these:

 With riding boots like these $35 distressed F21 boots:

Or these zigi soho Meena boots for $50 at dsw:

Jean shorts are the easiest boot + short look to pull off, and can be done in many ways.  My Edit (my favorite fashion blog) cutie wore an oversized sweater:

In fact, if you google "shorts and boots," you will find mostly jean shorts paired with the slouch styled boot from above.  You can find these boots anywhere these days, and cheap.  Definitely check out places like TJ Maxx, Ross, Marshalls and Target before spending $$ on boots.  True story: went to DSW and then Ross, the same boots that were $50 at DSW were $20 at Ross.  So glad I decided to check it out.  I got the perfect booties and the riding boots below.  Oh!  And high socks and a pack of tights for cheap.  They had a lot of Betsey Johnson socks and tights too.  See my $32 Kensiegirl riding boots with red zipper (originally $99- as most riding boots are around this price) for $32 from Ross:

Anyway, for more inspiration on boots and shorts, do a google image search, or lookbook search.  Give it a shot before it gets too cold!  And promise me you won't do this:

(sorry brit brit) image found on google.