secondhand styling adventures: sailor dresses
styling items from my treasure trove of online finds
Back in May, I spoke to
for her series Behind Closet Doors, focusing on personal style, shopping second-hand, and my current inspirations. When asked what was on my wishlist right now, I mentioned that I’d been on the hunt for a sailor dress but hadn’t found the one quite yet.I am very happy to say that I have finally found “the one” after many weeks of searching up and down my favorite secondhand apps. It’s bright red with a dropped waist, pleated skirt, navy and white striped piping on the collar + waist, and was only $18.
In the process of finding this one, I have gone through and saved many options of various colors, prints, and materials. Part of the fun and the frustration of this search came from the fact that there are so many styles underneath the umbrella term of “sailor dress”. I’ve styled three of my standout favorites in ways I would wear them had I picked them, hopefully providing you with a few ideas as well.
circus striped seafarer
The first look is built around this amazing navy and white striped dress with round pearlescent buttons down the front. I love the combination of red white and navy and believe that it can be worn without feeling too patriotic. If I had this dress, I’d wear it with my red camper mary janes and a pair of slightly scrunched red socks. I’ve worn this shoe-sock combination on a number of occasions, and I just really like the monochromatic look. With all of this collar space, I can’t help but want to add a pinback button. I’ve sourced ones with a bit of red in them in order to distribute the color throughout the outfit. I’ve been obsessed with a bunch of these 1940’s era buttons with cheeky sayings, they are all over etsy and eBay. The all red one instructing you to “FAKE IT!!” is 70’s era but just as intriguing. Fake what? I guess it’s up to you.
scout at sea
This second outfit is centered around the most sailor-y dress of the three. It looks grey in the images but according to the seller, it’s actually an army green which is quite unique for the style. Because of the white stripes along the collar and waist, I’d pair it with white shoes just to keep it going. A vintage Ferragamo pair I own (and I have seen available online) are pictured, but any low profile mary jane or flat would work. I’d mimic the monochromatic shoe-sock combo from the first look again here with a pair of white knee high socks. I quickly realized that this particular detail is reminiscent of the von Trapp children in the Sound of Music, but I’ve always loved their outfits so I consider it a plus.
Because there is already some sort of embellishment on the collar, I won’t be using any pins this time. However, I do have a heart shaped locket that I wear quite frequently and would probably wear with this so I included a few cute vintage options. Finally, I wanted to find a bag that kept the look from feeling too dressed up but was still cohesive. The color of the dress led me to think about Boy Scout backpacks and while searching for those, I came across these much less bulky canteen bags. I think they’re super cute and the perfect size to hold a little wallet and other miscellaneous items.
siren slugger
This final look is built around a lace option with a knotted collar. This particular dress has an attached lining so nothing underneath shows, but I have it styled as if it were sheer because that’s more fun. With a dress like this, I think a bodysuit/leotard situation would be the most comfortable option, but I also like the idea of just undies and committing with no bra. The undergarments pictured are from ARQ who aren’t selling currently, but still stock in a few smaller online boutiques. Further reversing the delicate vibes of the white lace, I would wear a heavier pair of boots on feet. My go-to’s are a pair of calf high Doc Marten 1b99’s I got on depop for a steal a few years back, but I could also see a campus boot or some biker boots working perfectly. Because I cannot wear an outfit without at least one accessory, I’ve included a few vintage wool caps to top everything off. Baseball caps are so ubiquitous that they don’t necessarily have to “go” in order to work, but these do complement the lace and the overall juxtaposed vibe nicely.
I hope that these little collages were fun and provided some inspiration. As always, thank you for reading! <3
happy to see your posts again on my feed and the outfit collages ! so well done and reminds me of my polyvore days back in 2015
The dress is SO good!! Glad you found the right one! ❤️