I totally agree lyn67 - I definitely want the contrast and the deep, one fold look (which is what makes it trickier than rolling a boyfriend jean for example, where one has some room to play to get it right).

Everlane had my number today with both the jeans and a similar colour woven top, quite discounted from the prices shown here. Plus I had to try the Square Shirt (thanks LaPed!).

I have TWO pairs of those blue cuffed Everlane jeans and love them.

I’ve had this same photo on my phone for weeks now - quite obsessed with this look.

Regarding the jeans : I have had a few pair of these deep cuffed jeans over the past couple of years , and just recently bought a precuffed pair of high waisted Girlfriends in a medium wash from Gap . I did have a pair of dark rinse straights with the big cuff but they were pretty leg shortening on 5’5” me . These precuffed pair are great because they also sit better than had I cuffed them myself . I’m really curious about replicating this look for myself too , but am not convinced I can wear a shirt buttoned and tucked that way either . We’ll see .

I noticed the shoes and bag compliment each other well, although I am not sure what co.or the bag is, maybe silver, but it has a black shoulder strap. Nothing seems to draw the eye away from the model and her beautiful smile.. The whole outfit seems to feature her. No great contrasts or brights or jaunty prints to draw the eye; a sort of column of neutrals or earthy tones.

Hi Joy, I agree with the observation that the outfit is harmonious with the wearer. I think this is part of the appeal for me too. I also noticed the purse and my thought was that the thin strap makes it a feminine touch in the otherwise boyish outfit (they could have left off the bag entirely). I myself have a fairly boyish brown messenger bag which I think would take the outfit into more tomboy, even newsie territory. Or conversely, a couple of chain purses which would feel more feminine and styled, I think. Finally I do have a wallet-on-a-string in a similar shape but it’s in light grey and bush, which are in my spring/summer palette and wouldn’t be great with my loafers which are brown and black. However it does work with my sneakers.

Just want to add that I absolutely love this look. I have dark wash straights from CQY that I love and will use to replicate, but as Angie suggested they do fit more like skinnies (especially with COVID weight). I think the dark rinse is essential to the retro look here - very James Dean.

Ah ha viva, I absolutely have a fondness for both James Dean and classic rockabilly guy looks - influenced by my dad and in particular the time he took me to see Johnny Cash (touring with June at the time). I was about twelve years old and not really sure if this show was cool or more of a dad thing but then looked around and saw a bunch of good looking young guys dressed in retro looks! And now I'm of course eternally grateful I saw an absolute legend in concert.

Jules, that is an amazing story. You were a lucky girl! It's funny but I feel very close to my 12-year-old self when I think about fashion. I haven't veered all that much from how I grew up. It seems like you, too, have a strong sartorial connection to the past.

You've got a load of great advice and just adding that with these minimal looks the details are key; for example her shirt looks perfectly starched, etc

I think the sweater you posted with semi truck and crisp cuffed jeans would look great!

Love the look. What immediately jumps out at me is that she is casual (bare ankles, casual purse, denim and cotton washable fabrics, girlish hair style) but still very neat (cuffs precise, denim is clean dark wash, shirt is ironed and buttoned, colors are subdued). Casual but neat, girlish but pulled-together in a responsible adult way.

Hey everyone just wanted to update that my Everlane order was successful, thanks to everyone's tips here. Specifically the jeans RunCarla suggested which I nabbed once they came back in stock and at a great discount, Angie's fit tips that help me remember to wear them high rather than slouchy (I might get the waist taken in, but can wear a belt for now), and LaPed's square shirt suggestion, but as it is quite long and voluminous I decided to tie it in front as Gigi suggested. The overall effect of the tied up shirt and jeans is definitely a bit retro, as viva identified!
As it turns out I don't love the jeans with my loafers as much as I expected, and my favourite shoe pairing is actually my pink Birkenstock Buckleys, which is fun since they are more casual/less office and also my newest transitional shoes which were bought kind of wishfully last year for post Covid outings. There's definitely an argument to be made that my outfit has a different vibe than the original -softer, prettier, less tomboy - but I feel like with your help I made it work for me in a way that's more true to my actual style, which incorporates more feminine details in with the boyish stuff I love but my face and figure fight with a bit.

This looks great. Glad it worked out for you. The forum is a wonderful place to go for help, isn't it?