21 Oversized Transitional Styles That Are Secretly Super Slimming

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When it comes to fashion, many people assume that all oversized designs drown out your shape. But that’s simply not the case! Just because a silhouette is slouchy doesn’t mean it’s not slimming. Relaxed-fit styles can actually flatter your figure more than form-fitting ‘fits! Looser looks not only provide tummy control, but they’re also extra comfy and stylish.

As we prep for the new season, we’re shopping for flattering staples we can take from summer into fall. Here are 21 oversized transitional pieces we think you’ll love!


1. This short-sleeve maxi dress is extremely comfy and surprisingly flattering! Plus, it comes with pockets (always a perk) — originally $53, now just $37!

2. No one will believe you scored this gorgeous geometric maxi dress from Amazon! “This has quickly become one of my favorite go-to dresses!” one shopper gushed. “Can easily be dressed up or dressed down and I always get compliments” — just $40!

3. Part beach cover-up and part tunic, this V-neck dress with 3/4-length sleeves is boho-chic! “This is a perfect lightweight loose dress that’s perfect for hot days or layered during early fall,” one customer declared — just $20!

4. This striped button-down maxi dress is channeling Jenna Lyons from The Real Housewives of New York City — just $27!

5. Confession: this isn’t the first time we’ve recommended this asymmetric tiered maxi dress. But we couldn’t help but spotlight the beachy beauty again — originally $60, now just $45!

6. This brand-new sweater dress just dropped on Amazon, and we’re already obsessed! “Really good Free People [lookalike]!” one reviewer raved. “Quality is great and price is so cheap” — just $33!


7. Lightweight yet warm, this ribbed knit long-sleeve V-neck shirt feels like something you’d find at Free People — originally $43, now just $35!

8. This oversized off-the-shoulder white T-shirt drapes like a dream! Team this top with your favorite blue jeans — just $20!

9. Business babe! This striped button-down shirt has a boyfriend fit with feminine smocked cuffs — just $27!

10. This flowy button-down top with 3/4-length sleeves is silky-smooth for late summer and early fall — originally $27, now just $20!

11. California dreamin’! This Los Angeles oversized graphic tee looks like it’s by an expensive designer brand. Style this shirt with biker shorts and sneakers with tube socks for an off-duty outfit — just $17!


12. Cozy and warm without being bulky or heavy, this quarter-zip pullover is totally trending for fall! “This is super soft and flattering with leggings or jeans,” one shopper said — originally $56, now just $37!

13. This viral striped crewneck looks like a Free People find! According to one review “This sweater is SO soft, flattering, and perfect for dressing up or down!” — originally $48, now just $41!

14. Hopped off the plane at LAX with my dream and my cardigan! And this oversized cardigan is lovely for layering in transitional weather — originally $36, now just $33!

15. Long enough to wear with leggings, this slouchy sweater is heavenly soft — originally $64, now just $37!

16. This oversized V-neck pullover is screaming fall fashion — just $43!


17. Thanks to the high-waisted fit, these baggy jeans are still super flattering (not to mention fashion-forward) — originally $80, now just $42!

18. Cargo pants are one of the top trends for fall 2023, so stay in style with this relaxed-fit look — just $38!

19. These satin wide-leg pants feel like pajamas but look far more luxe — just $21!

20. With over 43,000 reviews on Amazon, these high-waisted palazzo pants are wildly popular with shoppers — originally $30, now just $20!

21. Made from linen-blend material, these white loose pants are perfection for end-of-summer — originally $33, now just $27!

Not done shopping? See more of our favorite products below:

This post is brought to you by Crumpe’s Shop With Us team. The Shop With Us team aims to highlight products and services our readers might find interesting and useful, such as wedding-guest outfits, purses, plus-size swimsuits, women’s sneakers, bridal shapewear, and perfect gift ideas for everyone in your life. Product and service selection, however, is in no way intended to constitute an endorsement by either Crumpe or of any celebrity mentioned in the post.

The Shop With Us team may receive products free of charge from manufacturers to test. In addition, Crumpe receives compensation from the manufacturer of the products we write about when you click on a link and then purchase the product featured in an article. This does not drive our decision as to whether or not a product or service is featured or recommended. Shop With Us operates independently from the advertising sales team. We welcome your feedback at ShopWithUs@Crumpe.com. Happy shopping!

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