Inspiration Boards: Cuffed Jeans with Brown Shoes

Inspiration Boards: Cuffed Jeans with Brown Shoes

Try it tomorrow
cuffed jeans, rolled jeans, rolling your jeans, cuffing your jeans

By Megan Collins | Last Updated: Jun 23 2022 | 2 min read

I went to a wedding in the city last weekend – the last on my jam-packed calendar o’ celebrations til September. The bride looked lovely, I may have cried a little at the “I now pronounce you…” part, and I ate cake with my fingers when the caterers ran out of utensils. All that to say, I thoroughly enjoyed myself.

I also felt like I’d stumbled onto the after party of a polo match, not the crowd at a mostly-Texan-transplants-in-NYC wedding. And I mean that in the best way possible. Preppy chic, nom nom.

The reception was held at the Grand Army Plaza on Prospect Park West in Brooklyn. With a surprisingly spacious backyard area, it felt refreshingly non-city-ish, quite a feat considering it was only a train ride away from home for me at the end of the night.

Finding myself overdressed in a cocktail dress and heels, I proceeded to not-so-surreptitiously take some candids for inspiration. With an adorable mason jar of lemonade in one hand and iPhone in the other, I managed to snap some pics for your viewing pleasure. Yes, they’re blurry; no, the lemonade wasn’t spiked. (*cough*someone get me a new camera please*cough)

With so many guys in denim, the overall effect could have veered towards a VA hall reception/wedding cake from Costco atmosphere, but instead it felt…comfortably elegant. Lots of bowties. Lots of chambray. Lots of summer plaid. A couple pairs of suspenders. it was awesome.

The biggest takeaway though? Dark jeans cuffed at the ankle, worn with brown dress shoes. Loved it.

I always thought a cuffed jean cuff on a guy was a more intermediate-level move; unlike the rolled chino I talked about earlier this week, it can get a little Fonzi if you’re not careful. But this weekend has me reversing my stance.

The look can be done by a guy who doesn’t consider himself super-fashion-y (the technical term) as long as the pants are slim enough (you don’t want to look like one of those dudes walking on the beach in a Viagra commercial), the shoes are shined (or artfully scuffed) and the socks are non-existent (or at least hidden well below the sight line).

Look at those pictures – two of them have dudes wearing cuffed jeans and brown shoes in the background of other cuffed jean and brown shoe-wearers!

Pair your own cuffed jeans and brown shoes combo with a tucked-in button down with the sleeves rolled up, or under a casual summer blazer. Top it all off with some stunna sunglasses – Wayfarers are always a solid choice – and that aforementioned lemonade in your hand. Though I might suggest spiking it with bourbon. Because that tastes delicious.

I started Style Girlfriend to help guys look, feel, and act their best.