Winona’s Style Challenge: Find Me Curve-Conscious Dresses For Under $150

Winona’s been craving a style makeover. She wants to change up her wardrobe and add some spiiiiice with some bombshell-style fitted dresses that really accentuate her va-va-voom curves. (Think “Mad Men”‘s Joan Holloway for reference.) The trick, of course, with this 1960s silhouette is looking cute without veering to close to costume-y. You’re not in the touring company of “Hairspray,” after all. If you’re craving some retro-fied curvy numbers, there’s a bevy of online options. Shops like Shabby Apple, Bettie Page Clothing, Daddy-O’s, Unique Vintage and Trashy Diva are all great resources if you’re looking for reproductions of styles from the ’40s, ’50s and ’60s, while sites like Modcloth offer more modern takes on those designs.

But getting back to Winona! I’ve chosen five curvy and cute dresses that she can wear day or night––for less than $150 each!

1. Modcloth American Glamstand Dress, $147.99
2. Coldwater Creek Hourglass Stripe Dress, $129./95
3. Trashy Diva Trixie Sarong Dress, $97
4. White House Black Market Faille Peplum Sheath Dress, $89.99
5. Unique Vintage First Rate, First Mate Olive Green Wiggle Dress, $136

Click through to see how we’ve styled ‘em!

winona style challenge daytime outfits

Trashy Diva Trixie Sarong Dress, $97
Arrow Cut Out Leather Cuff, $26
DV by Dolce Vita Faline Wedge Sandal, $55
Flat Head Stud Wrap Bracelet, $24.90
Coldwater Creek Hourglass Stripe Dress, $129./95
Sphinx Collar Necklace, $25
Kelsi Dagger Sandals, $99
Unique Vintage First Rate, First Mate Olive Green Wiggle Dress, $136

winona style challenge date night outfts

Modcloth American Glamstand Dress, $147.99
Modcloth Professional Prerequisite Heel, $34.99
Arrow Cut Out Leather Cuff, $26
Sphinx Collar Necklace, $25
White House Black Market Faille Peplum Sheath Dress, $89.99

Want me to take on your style challenge? I am sooooo up for it! Really, I love shopping for other people. That’s weird, right? Shoot me an email at julie@thefrisky.com and tell me what you’re looking for!

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