Let’s Try The Wrong Shoe Theory: Trousers + Dad Sneakers


I had been trying to wear trousers for years, but something always felt a bit off every time I would go to pull a pair on. The trousers just never felt like me in the way I wanted them to (“so long” to all those trouser Pinterest outfits I wanted to re-create!).

But I recently figured it out: it’s the pleated detailing that adorns most styles of these work-ready pants that I don’t love (like, at all).

I had mostly written off trousers as something I would be able to rock in my personal wardrobe following this realization…that is, until I found these wide-leg trousers from GapSANS PLEATS.

* Gap’s currently offering this lovely perk: Take an extra 20% Off your purchase with code ADDON (valid 10/16-10/22) *

We're testing out the Wrong Shoe Theory to help style these wide-leg trousers from Gap. Will dad sneaks do the trick?

trousers (8 Tall) | similar tee | shoes | similar jacket | similar bag

Gap’s High-Rise Wide-Leg Trousers: How I’m Wearing Them For Fall

Gap’s trousers are lightweight, comfy, and come in both regular, tall, and petite sizing. I grabbed the tall inseam, one I truly didn’t need at 5’9”, but they were just the extra-long length I was specifically looking for.

As I played around with styling them up in my own wardrobe, there was one consistent look I was falling in love with — trousers + dad sneakers. 

Chunky dad shoes are the “wrong shoes,” if you will, when pairing with classic trousers. 

Which is exactly the reason I love them. 

Since I don’t work in an office, I am drawn to the idea of styling trousers in a casual, street-wear ready outfit, and casual, comfort sneakers are just the ticket. To top off the whole look, I love an easy, sporty tee and a wool bomber jacket. The entire outfit screams FALL in the coolest of ways.

Check out the video below to watch me style the whole outfit, and listen as I go a bit more into detail about why this entire outfit will be repeated all fall and winter long! Xx

Outfit Links & Similar Finds:
Trousers– Comfortable, true to size, and tempting enough to buy in multiple colors.
Similar tee– Nike always has the coolest graphic tees, but you usually have to act quick before they sell out (like mine did!).
Sneakers– I’ve owned these for many years and their comfort has gone unmatched.
Similar sneakers– My dad sneakers in this video can be tricky to find in stock, but this new pair from NB is very similar in shape and incredibly comfortable.
Similar jacket– Wool bomber jackets are having a moment, and while mine is old, this one is extremely similar (and check out this wool bomber with the cutest pearl pin on the front, swoon).
Similar bag– My puffy black purse is from AllSaints a few years back, but they’re always putting out similar versions each winter that are equally as good (and the quality is 10/10).


Let’s be friends on Instagram! Sharing life from a California beach town, daily style & beauty faves, and never ending Gilmore Girl binge-athons – all with a good dose of adorable toddler content, too.