4 Ways to Wear Vintage-Inspired Dresses
I love dresses. I have recently developed a strong aversion to pants and now spend most of my time in dresses with tights or leggings. They are simultaneously super comfortable and very cute!
So I thought I would show you guys a few ways to wear some cute vintage-inspired dresses, with emphasis on how to wear them for fall! The secret to pulling off these dresses is to wear them with modern pieces and in most cases, just keep the look simple.
Outfit #1: 1970’s Chic

Product Information: Pumpkin Spice Latte Dress – ModCloth, Chocolate Ankle Legging – Miss Selfridge, Brown Cord Blazer – American Eagle Outfitters, Graduate Boots – American Eagle Outfitters, Hibiscus Bangle – ModCloth, Carnelian Drop Earrings – Refinery 29 Shops.
I love the orange color of this dress – it’s orange without being orange, you know? It’s the perfect color for a beautiful, crisp fall day where the weather is just a bit chilly. This dress reminds me of the 1970’s – the eyelet accents and the ties on the sleeves are very reminiscent of dresses from that era. At the same time, this dress is modernized with a shorter length and emphasis on the waist.
I paired this dress with shades of brown because neutral tones make the beautiful orange stand out. I added some pretty teal accents through the bracelet and earrings for an overall look that is super chic but still allows the dress to be the focus.
Outfit #2: Cute as a Button

Product Information: Sabrina Sweater Dress – Delias, Pink Long Sleeve Top – Peacocks, Eggplant Tights – American Eagle Outfitters, Black Patent Flats – Torrid, Purple Resin Bangles – Dorothy Perkins, Little Sparrow Necklace – Tilly Bloom.
This gray dress is adorable and reminds of something that a very prim, yet chic girl would have worn in the 1940’s or 50’s!
The buttons and uniquely shaped neckline set this dress apart from the rest. But that’s no reason not to make it yours with a few fun pieces.
As I was putting together this outfit, I decided to put a long-sleeved top under the dress because I love the contrast between the gray dress and the pink top. In addition, I wanted to show some options for girls who don’t like to show off that much of their chest. Of course, you could also nix the shirt and add a cute purple cardigan to keep warm! I think this would be a great look to wear out with friends for some shopping or to lunch – very casual, but still very fabulous!
Outfit #3: Sailor-inspired

Product Information: Sailor Mix Dress – Republic, Black Cardigan – Asda Direct, Red Flats – Wanted, Rose Ring – Forever 21, Heart Necklace – Butler and Wilson.
Can I just tell you guys how much I love this dress? It is so cute – sailor inspired, very retro 1940’s, and so cute! I love the bubble skirt (very 1980’s!), I love the red bow, and I love the very simple neckline. It’s just fabulous.
I paired this dress with very simple pieces: a black cardigan worn open, some cute jewelry, and red flats. I love the feminine quality of this dress – it is just so flirty! I think this would be a great look for going shopping with your friends, or you could add tights and high heels and wear this out on a date!
Outfit #4: Mod Squad

Product Information: Multicolor Sequin Dress – Republic, Faux Leather Jacket – Tilly’s, Opaque Tights – Oasis, Purple Pumps – H&M, Union Jack Sequin Clutch – Monsoon, Celebrity Style Earrings – Fantasy Jewelry Box.
This dress is very mod-inspired with a bit of added sparkle. The variations in color are great because they mean the dress can be paired with just about anything.
For this look, I styled the dress for a night look because I would definitely wear it on a date or out dancing. I love the combination of this bright dress with a few simple black pieces, colorful pumps, and a fabulous clutch. In regards to the bag, I chose a similarly colored, sequined clutch, but if that’s a little much for you, the dress would also look great with a more simple option.
What Do You Think?
What do you guys think about these dresses? Which is your favorite and how would you wear it? Let me know in the comments!
Posted on on October 11, 2009 / Filed Under: Fashion Tips / Tags: Dresses, Vintage, Vintage-Inspired Fashion
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Isabelle
I’m such a fan of the sailor-inspired outfit! Makes me want to take a boat to sea and enjoy my weekend!
Vivi
I LOVE the first outfit! More vintage inspired outfits please! Keep up the good work!
Brooke
I LOVE outfit number 2! Mostly because of that dress. It’s possible I have to have it. Do you know if the AE tights are warm?
Luinae
I am in love with these posts- you have such fantastic taste and I love vintage clothing!
Outfit 1- OMG, love! The only thing I would do is where it with tights and not leggings, but other then that is is perfect. Just perfect.
Outfit 2- Again, love!! It is beautiful and I love the dress. The one small change I would do to make it “me” is add a teal top instead of a pink one under the dress.
I like outfits 3 & 4 as well, but the first 2 are simply divine.
Great work!
Michelle - College of Idaho
Brooke – yes, AE tights are very warm! I bought two pairs of their tights last Saturday and they are the warmest, comfiest tights I own. :)
Milana
I think there are items that are nice but too messy in the outfit. Center the dress – don’t try to dress it up if it’s dressy enough like the Mod Squad.
I like your blog!
Sam
I love your posts! I love the first two outfits the best. You give me such fashion inspiration! Keep up the great work.
Sarah
The first outfit wins.
I’m also hating pants recently.
I like how the 4th outfit is too sparkly but in a good way.
Jessie
All very nice! Great taste!
Kat
Oh my god, we NEED to go shopping together. I love the outfits you picked out here, especially the first three. If I had to choose just one to take home, I’d probably pick #2. That gray dress is just so girly and cute. I want it!
Great work! I’d love more posts like this.
Cara
J’adore the grey dress! I hadn’t thought of layering it over just a tee, and I have tried it on before and the neckline wasn’t right on me without at least a cami. Now I can wear it at least two ways – tee AND cami – though, so back to Delia’s I go :) These outfits are all beautiful, and I agree; skirts are so much more comfortable and just make every day a little bit happier and better. Hurray femininity!
Maria
I’m absolutely in love with the sailor outfit! I also LOVE the grey dress, though I’m not seeing myself wearing it with a tee or cardi… the dress itself is just too funto hide! :) Great post! Please please please post more vintage-outfit-inspiration!
Lady In Evening Dress
I love the second outfit and i am in love with your post..
Tasha
Oh my… So many sequins… Red and white stripes remind me of candy-canes… Love the other two, though… :)
Alana @ The Comm Ave Strut
Love these looks! Great job :)
Leia
I love, love, love dresses, and would wear them every day if I had enough of them!
B.
So I think a lot of other people had the same idea as me in that they fell in love with dress #3 and went directly to republic to get it. Fortunately, it’s on sale! Unfortunately, there are only 2 sizes left (not mine) :(.
But I love love love it!!!!!!!
Paola
I love all of the outfits, especially the sailor inspired one. But i can’t seem to find the sailor inspired dress anywhere on the republic website. Do you know where else i could find something similar to it?
Michelle - College of Idaho
Paola – I know the dress was on sale when I first chose it and it was in very limited sizing! It probably got sold out which is a major bummer! I would keep your eyes peeled on sites like Forever21 and ModCloth because they get LOTS new merchandise everyday. If I find anything similar, I will definitely post it! :)