Retro inspiration | Sailor-style trousers

A few years ago, I did a collage of me and my maternal grandmother, the side of my family that I most resemble, and that post remains one of my very favorite posts. (And y’all recently enjoyed a collage of me and my mom for Mother’s Day!).

Back when I did the post of my grandmother, I mentioned that I had a few different candid photos of her with the idea that I would do more posts of me wearing outfits inspired by her. I didn’t immediately follow up on that idea (sorry!), but I’ve never forgotten that idea. So when I was recently going back over those old photos of my grandmother, I realized that I now had another piece in my wardrobe, a pair of sailor-style pants I picked up this past fall, that I could wear for another retro- and family-inspired look.

Librarian for Life + Style | Retro inspiration, sailor-style trousers

Librarian for Life + Style | Retro inspirations

I basically recreated my grandma’s look with modern versions, starting with my wide-legged, sailor-style trousers. I then thought of my black wedge sandals, which looked a little similar to the bit of her black shoes visible in her photograph. I echoed her polka-dotted button-front blouse with my own diamond-print button-front blouse (the print looks like tiny polka dots from afar). And my new black tote bag is structured enough to play off the hard case she’s carrying in the photo.

I then carried my black rain coat when we took photos, to more closely mimic the inspiration photograph.

Librarian for Life + Style | Retro inspiration, sailor-style trousers

Librarian for Life + Style | Retro inspiration, sailor-style trousers

Librarian for Life + Style | Retro inspiration closeup

And y’all know me and details! I filled in my eyebrows a little more heavily and went red on the lips for a more ’40s makeup look. (The matte finish on my laps is due to just using red lip liner on my lips, instead of red lipstick.)

I think one of the main reasons I didn’t immediately do more of these retro inspiration looks of my grandma’s is because I cut my hair all off later that year into a ’20s-inspired bob. Since my grandmother’s look in these photographs is so clearly from the ’40s, I didn’t feel I could really channel her in the same way that I had in that first post.

I still have short hair, so what made this time different? First, I no longer have the blunt, ’20s-style bangs I used to have, and my bangs are long enough now to play with. My recent hair experiments with the Kenra hairsprays have also given me more confidence in playing with my short hair! Therefore, I decided that I could do a slight nod to the ’40s hairstyles with a little pin curl of my bangs. So I rolled my bangs over and into a slight curl at the end, and then pinned and sprayed the bangs. It’s subtle, but it was enough for me. 🙂

Librarian for Life + Style | Retro inspiration, sailor-style trousers

Librarian for Life + Style | Retro inspiration, sailor-style trousers

Librarian for Life + Style | Retro inspiration, sailor-style trousers

Weather:  Cooler but dry

Where:  Work day that included meetings


Shop my outfit:

very similar polka dot button-front shirt  //  similar wide-leg black trousers  //  very similar black strappy wedges  //  exact black tote bag

Librarian for Life + Style | Print button-front and wide-leg trousers outfit collage

Did you enjoy this post and another outfit inspired by my grandmother? Do you have a favorite era for retro style inspiration? Please leave a comment and share!

Linkups:  Hello MondayVisible Monday, #iwillwearwhatilikeShoe and TellConfident TwosdaysTurning Heads, Style With a SmileWho’s Wearing What WednesdaysTrendy Wednesday, What I Wore Wednesday, I Feel Pretty Wednesdays, Weekly Wednesday Fashion Linkup,  Whatcha Wearing WednesdayTop of the WorldThursdays Fashion Files, Thursday ModaCelebrating StyleFashion FridayPassion for Fashion, Fun Fashion FridayFabulous FridayFriday Favorites, Fancy Friday, Flashback Fashion FridayFine-Whatever LinkupWeekend Wear Link Up#SaturdayShareLinkUp


16 thoughts on “Retro inspiration | Sailor-style trousers

  1. Brenda N

    Love the 40’s inspired look, Jen. Your hair works really well with it. You & your grandmother look like sisters! I have a little black & white photo album of my mom’s fashions from the 40’s, one day we went through it together & she told me the colors of all the clothes, that was so fun & I treasure those photos. 🙂

  2. Phyllis

    Dear Jennifer,
    Thank you for doing that pose of Mom to imitate. This is the first time that I noticed the overnight bag that she is carrying. We used it for years while going on trips. I guess I thought that it had been bought after my parents married. However, I always wondered why the overnight bag never matched the other luggage pieces! Now I know. Thanks!
    Love, Mom

  3. Jennie

    Love his look, Jen, with its retro vibe. The photo of your grandmother is fantastic. She has wonderful style and looks so confident!

  4. Pingback: 25+ Times People Recreated Their Grandparents Photos, And The Result Was Amazing - Just Girly Things

  5. Pingback: 33 рази, коли онуки зробили фото точнісінько, як у бабусі і дідуся | ОТОЖ

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