We have come to August, the time of summer when I start truly thinking about fall style. Of course, it doesn’t hurt that I have some new goodies in my closet that are waiting for cooler weather.

I’m thinking about hemming these Paige jeans to wear with my lowest heel booties and also with sneakers. I’m interested in exploring the rather trendy bootcut + sneakers look because both items appeal to me and suit my lifestyle well.

However, I am treading with caution because bootcuts with sneakers were a default for me in the early 00’s and not in a fashion-forward way. I want to make sure it looks intentional and cool, not frumpy. Sneakers are not exactly an elongating, flattering way for the eye to end when traveling down an outfit, so I think I can accept a certain level of JFE, considering that bootcuts are usually inherently flattering on me.

Here I am in the Paige jeans, and here is my current sneaker collection (not counting my actual workout shoes). Most of these are quite flat and low-profile, and it seems the current trend is for a bit more substantial or platform sole on the sneaker.

Pic 2 l-r Superga navy blue metallic, silver Cole Haan, rose gold Dolce Vita

Pic 3 l-r Steve Madden metallic mixed media sneaker (open on sides so limited wearing season), Nike black and white patterned (not super comfortable, fit has always been a little off, so maybe due for replacement), random grey/black sneakers (also could be talked into letting these go if they look kind of dated - they were cheap).

Pic 4 - Converse black leather high tops.

I like these NAS sneakers in the Fonds but of course I waited too long and they are no longer on sale.

Does anyone have any good recommendations for a trendy update in a sneaker to wear with bootcuts for fall/mild winter? I would consider white but would prefer not solid white — maybe white with a black or grey side stripe? I don’t think the super thick dad sneaker is for me. I’m more drawn to the more streamlined look of the Vans or something like that, but with a substantial sole.

Does this sound like a good strategy? Up to date enough? I welcome specific visuals or finds if you care to share.