I think wearing a dress with boots is adorable. It reminds me of Lorelai Gilmore, and it's a perfect mix of feminine and rugged/boyish/comfortable/whatever you want to call it -- which is exactly what I'd like my college style to be. I guess for regular dress-wearers unlike me, this must be quite a common look in the fall, but for me it's something of a novelty and anyway I've found some really nice dress-and-boots ensembles that I just need to show to the world.
The J Crew fall lineup is full of gorgeousness. This is one of the best looks. I really rarely wear dresses, but if I'm going to invest a dress anytime soon it'll definitely be a shirt-dress in a beautiful deep colour like this one. And I'm loving the cute cap!
Yeah I do love the J Crew fall looks very much. Which is why I'm going to pretend that this is a dress. Which it isn't, but it is a skirt-with-boots outfit and the skirt's the same shade as the incredibly pretty antique blouse so let's just pretend it's a dress okay? In fact you could take an off-white or cream dress in a similar shape, loosely fasten a dark-coloured leather belt around the waist and you'd have a very similar look. It's so cute and young-looking with the messenger bag and the boots and the way the skirt's slightly rumpled, which is how our skirts are going to look when we're busy being college girls, right?
This dress is very femininely drapey and flowy but the boots which are almost the same brown/grey shade just give it a fantastic shot of attitude.
This is called "Classic Grunge" in shopbop's fall trends. Heavily layered, it edges dangerously close to Mary-Kate Olsen bag lady territory but just manages to stay chic, and does offer some interesting ideas to continue working the dress-and-boots look when the weather gets even colder. I'd probably go with slightly brighter, bolder or deeper colours in order to look less muddy, though. I covet those laced-up Kors boots.
I just really like this picture from the anthropologie fall catalog. I wish I could see the rest of the dress, it looks really cute with the patterned tights. Beware of patterned tights though, they're generally avoidable if your legs are even a hint thicker than models' regulation stick-figure legs. Still, they're fun.