How Can I Go From Punk To Pinup? 

A few ideas for translating your signature style to the warmer months and adding some new outfits into the mix . . .

Asking for fashion advice can feel daunting, even shaming—unless you're a white, cis, blonde size 2, it can often feel like an entire industry has banished you to the land of Frumpdom. Well sucks to that, we say! Fashion is for everyone—fat girls, feminist girls, girls who get cold really easily, and girls who just don't feel "girly" alike.

To help us create an inclusive platform for fashion knowledge, we've asked our resident aesthetic ace Winona Rose to answer our questions—and yours!—about how to look our best, even if the fashion industry has dealt us the worst of hands.

Dear Winona,

I really like shirt dresses. I have Modcloth's soda fountain and hepcat dresses in every available color. My every day look involves a shirt dress, a sweater, thigh-highs, and boots. I'd describe my style as "Professorial Punk Femme." With the warmer months coming, I want to embolden my vintage style, veering toward "pinup wannabe." With that in mind:

1) How would you "dress up" and accessorize a shirt dress for the warmer months?

2) What's a sensible heel to wear with the dresses in these pictures?

3) Can you help show me a different dress style that's similar enough to "collared shirt dress" but will let me transcend into other styles and get me out of this rut?

Disrespectfully Yours, Because I'm Not A Part Of Your System,

Dear Jetta,

First off, your style is fabulous and I love how you’ve carved out your own aesthetic to the point where it’s almost become a uniform. That being said, even the most on-point uniforms need a little freshening up sometimes (like when my painfully attractive mail carrier switches from long pants to shorts in mid-March), so I salute you for searching for some warm-weather updates and alternative looks that still feel like YOU. Here are a few ideas for translating your signature style to the warmer months and adding some new outfits into the mix . . .

Warm Weather Updates Wicker satchel

Check out vintage boutiques and Etsy shops for accessories that match your favorite fashion era but bring a lighter, summer-y vibe. In your case, think “Marilyn Monroe At The Beach” (MMATB for quick recall). You’re on the hunt for wicker satchels (with a bandana tied around the handle, natch), wide brimmed hats, and silk scarves, to name a few key accessories.

You can even keep your boots and thigh-highs in rotation as long as you don’t get overheated—just try lighter colors and materials (tan and cream instead of black and dark brown) than your go-to winter options.

Of course, a ridiculously huge pair of cat eye sunglasses is an absolute necessity. No question.

The Sensible Heel Dilemma

Finding a heel that’s cute, comfortable, and aligned with your style can be a challenge, but for you I think the answer is clear. Kitten heels are your new best friend. They’re comfortable enough to wear all day and embody the pin-up sex appeal you’re going for.

Curvy tweed shoesA mary jane style in bright leather or a curvy tweed version both check all the “professorial punk femme” boxes. For warmer months, try a peep toe kitten heel like these.

Branching Out

Alright, my suggestion for a different dress style isn’t technically a dress—but I hope you’ll still hear me out!

Your new spring outfit formula is—drumroll, please!—pencil skirt + tie-front blouse. It’s a sexy, retro combination that will look great on your body type and allow you to easily experiment with different prints and proportions. It’s also fun, flirty, and summer-y, which are the exact three adjectives you need to pull you out of a style rut.

Go for a pencil skirt that hits around your knee (either slightly above or below) with a high waist. For even more of a va-va-voom effect, opt for a skirt with a slight flare at the bottom. You can either look for a blouse that’s designed to be worn tied at the waist, like this one, or you can just leave the bottom couple buttons of your favorite collared blouse unbuttoned and tie the loose ends in a knot.

I love the look of a solid pencil skirt paired with a blouse with a fun print (think polka dots, florals, plaid . . . or all of the above?!).

Tie your blouse right at the waistline of your skirt to create an hourglass shape, but don’t be afraid to experiment with other looks too. There are so many options when it comes to blouse/skirt combinations and proportions—tie your blouse lower on your hips or higher up on your waist, or choose a lower skirt/shorter blouse and show a bit of midriff if you’re feeling daring and/or overheated. But seriously, try it out and have fun with it! You’ve got all the tools you need to go from “pin-up wannabe” to “legit pin-up” in no time.

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