Pinup Essential: Cultivating a Pinup wardrobe

When you are new to a style, it can be overwhelming to get started.  Where do you start?  How do you know what to get first and how do you start building a new wardrobe without breaking the bank?

If you have come this far, chances are you are drawn to and considering adopting the pinup style.  Congratulations on your first steps toward this fabulous, classy, and timeless style and possibly the lifestyle!  I am a bit biased, but I happen to believe that the pinup, retro, rockabilly, or whatever you want to call it is the greatest and most flattering style for all women.  The style revolves around femininity and embracing YOUR womanly shape, regardless of size.  By taking a quick browse around the vintage reproduction websites, you can see that women of all shapes and sizes look fabulous and feel fabulous when rocking these dresses.  I like that I can walk the line of being totally sexy, yet demure and classy at the same time.  That is something that’s almost impossible to pull off while wearing modern fashion, things that are either too tight, too low, too short, or often a combination of the three.  I am a college student, so I see girls walking around campus with everything hanging out, I can’t imagine they are very comfortable!  It’s amazing how in a sea of bare skin, I am the one who turns heads wearing a wool pencil skirt and a twinset!  It’s either that or they look very sloppy like they just rolled out of bed.

The best place to start when building your new wardrobe is to shop your closet and find things that already work.  Chances are you have been collecting things for some time that are retro inspired or are classic enough to incorporate into the “new you”.  Lets start with the basics, your wardrobe foundation.

You will need:

a pencil skirt

this one from JC Penny is $25 and available in a bunch of basic colors.  They are a little bit short for my taste and for true 50s style, I would prefer right under the knee for a more classic length.

This one is almost the same, but more expensive.  It is a little tighter, a little more sexy.  It all depends on your budget and how many places you are wanting to wear it.  For example, the office might not appreciate the extra tightness.  Pick your favorite neutral color, a color that goes with everything else in your already existing wardrobe.  Probably black or gray to start with, then add fun colors later.

I get most of my pencil skirts from thrift stores, they are true vintage and are very affordable.

an a-line or circle skirt or dress

This one is from Vivien of Holloway, here is the link

This is the Doris skirt by Pinup Girl Clothing. I have my eye in this one in black and I already have it in the atomic turquoise print.  I love the fit of this one and the fullness, it is really stiff so it holds its shape even without a crinoline underneath.

Unlike most of the items in this list, circle skirts and dresses are not super readily available at most stores.  This will be an item that you will have to splurge a bit on or spend a lot of time scouring eBay and thrift stores.  Its a good idea to become well acquainted with thrift stores, both in person and online, they will become your best friend for the pinup look.

a cardigan

This is such a basic wardrobe staple that chances are you already have at least one.  Most of mine are thrifted and solid colors.  But there are some really cute, rockabilly ones out there if you want to add some extra personality.  The cardigan is great to keep the cold away, to cover up your arms for more modesty/professionalism, and it gives you that “sweater girl” look that was so popular in the 50s.

t-shirts, tank tops, blouses, etc.

these can be literally whatever you want: band tees, plain t-shirts, tank tops, wife beaters, pretty much any top that you want to wear.  I would never buy plain shirts from the vintage reproduction sites, I don’t think its worth it.  I get a lot of basic t-shirts from Target.  I did recently purchase some Vamp tops from Pinup Girl Clothing and they are fabulous, I got the mint, purple, and peach ones (reviews and pictures to come shortly).  But they are a bit pricey so they can be something to work up to, once you are commited to wearing vintage/pinup all the time.

ballet flats

These are a vintage gals best friends! Ballet flats have a very retro look without having to walk around in high heels all day.  I found a pair of black patent leather ones at Payless last year for $15, I’ve been meaning to go back and get some more (if they still have them) but I haven’t gotten around to it.  Your best bet is to find some in a neutral color, black shoes go with almost everything, and try on a few so you can find ones that are comfortable.  It defeats the purpose to wear flat shoes if they pinch or rub your feet raw, so much for comfort!  Spring is the perfect time to stock up on ballet flats and espadrilles, they will be all over stores right now.

These are the ones I have:

They have them in a few other colors, and for $17 you really can’t go wrong.

wedges or espadrilles

Wedges are great, they are more comfortable than stilletos and are very true to the 50s.  They are widely available this time of year and can be found in closed or open-toe styles.  there are some really cute pinupy ones at payless right now like these:

killer heels

These are the most fun, but also the most frivolous.  They can be anything that you adore, let your personality shine!

These are mine:


One pair of many! I should buy more practical shoes, but whats the fun in that!

I have been wanting these for awhile: they remind me of Mini Mouse 🙂 and all of these are fabulous:

a wiggle dress

This is usually the first step into pinup-hood.  A lady will purchase a wiggle dress and they are stunned by how fabulous they look, so they go deeper into the look and often never look back.  This is where the vintage reproduction lines are the best place to go.  Pick your favorite color, whatever makes you feel beautiful and sexy, and rock the hell out of it! I am a huge fan of Pinup Girl Clothing, the Vamp dress and the Erin dress are wonderful wiggle dresses.  They come in a wide range of colors that will tickle any fancy.

I have the tiger print Vamp and can’t wait for an occasion to wear it, I’m thinking car shows and I’m hoping to get called for a Pinup contest in June and this will be my secret weapon 😉

Bettie Page clothing has some great ones

Stop Staring is wonderful, but a little more pricey than the others.  Though the quality is great

I recommend searching eBay, there are always dresses from these brands on there, usually very lightly used (ie tried on and doesn’t fit or worn to a wedding and never again) and you can sometimes get a major bargain.

That’s really all you need for the basic beginners wardrobe, everything from here is built on this and expanded, you will find your favorite silhouette and collect more of that type.  For example, you may love the way pencil skirts look and find yourself with a collection of 20 pencil skirts.  That’s great!  The best part of this and any “alternative” style is that it can be whatever you want it to be, there are no rules!  Enjoy your road to fabulous!


6 thoughts on “Pinup Essential: Cultivating a Pinup wardrobe

  1. I have those same Iron Fist heels! Great tips! Although to be honest I started my wardrobe with a pencil skirt, black pumps, and a vintage top, and then added in two dresses from Hell Bunny and three from Pug. One thing I think would be great to add is that if you go for a more modern/toned down pinup look, you get stared at less which might be nice. One of my favorites is a black turtleneck/high waist black denim pants, which is classy/50’s/sexy/ and oh-so-wearable in modern day (plus Audrey Hepburn rocked the look so you can’t loose)
    You’re so right about the wedges, my favorite pair of shoes is a pair of Black oxfords with leopard wedges, super cute and very wearable.

  2. Yeah, I’d say these are some pretty good basic tips for beginners. Fun fact about me…my “first step into pinup-hood” (by the way, “pinup-hood”, cool term) was actually with accessories 🙂 A little something for your other readers to consider as well 😉

    I agree about Dixiefried’s skirts..THE BEST! 😀 Have three so far and working on getting more. Great sexy retro length. They’re SO comfortable in my opinion and I can wear them anywhere. I see you’ve mentioned a skirt I also have my eye on, the Pinup Couture Doris skirt in black. I have yet to add a swing skirt to my collection, so I’m hoping I can get this when it comes back into stock in my size.

    Shopping around in thrift stores can be a true money saver, although I usually opt to buy most of my pinup clothing new online, since it’s hard to find things I like in my size (XL/2X) that fit well.

    As for shoes, It’s usually heels or wedges for me 🙂 My wedges although they’re pretty comfortable are 4″- 4 1/2″. If I were going somewhere I’d be walking around ALL day, I’d pick up a wedge with a smaller stature like 2″-3″. Either that or go with my half modern half retro rockabilly look and wear some cute sneakers.

    The wiggle dress… another item I’d love to get at some point, although pairing fitted pencil skirts and tops work well for the desired silhouette 😉 I do usually go more for separates over dresses. More cost effective over all. Mixing and matching gos a long way 🙂

  3. These are all great tips! I’m a college student too on my campus it’s all the same – lots and lots of skin! I believe that less is more, which is why I love the pinup look so much. The pinup look accentuates curves without leaving too little to the imagination – and it’s flattering on all figures! I’m so glad that I found the pinup look when I did, there were too many years in my life spent crying over not looking “perfect” in skinny jeans (which are unforgiving on womanly figures!).

  4. Circle skirts are easy enough to make. When I found the price to be a deterrent to buying ready-made, I found a pattern for $5 and made a few in the course of a day. You only have to worry about it fitting at the waist, so it’s a good beginner project, and you can make them in any color or print you desire.

    • That’s a really good point Kathleen. I have noticed poodle skirt patterns on sale after Halloween for super cheap, which is the same basic shape. I would love to be able to sew well enough to make my own clothes, since it is all a bit pricey, circle skirts are a great place to start 🙂

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