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Chicago Winter Packing Guide + Outfit Ideas 2025
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items Planning a winter trip to Chicago in 2025? Here's exactly what I wore to stay warm, stylish, and comfortable in the Windy City. From cozy coats to casual dinner looks, this list includes every outfit I packed. Perfect for city strolls, chilly nights,...
Sections
5
Accessories
Tops
Bottoms
Bodysuits
Shoes
Accessories
SHEIN Stackable Star Necklaces | Love the fact that they are not connected so I can mix and match with my other accessories. However, very cheaply made so unfortunatley most of them have already broken.
ROMWE Goth 3pcs Star Charm Necklace for Women - Fashion Zinc Alloy Jewelry
SHEIN Stackable Heart Necklaces | Love the fact that they are not connected so I can mix and match with my other accessories. However, very cheaply made so unfortunatley most of them have already broken.
4pcs Vintage Heart Pendant Necklace Set for Women - SHEIN USA
SHEIN Stud Heart Earrings | Very cute stud like earrings
Heart Design Stud Earrings - SHEIN USA
Tops
SHEIN Jersey T-Shirt | I like it but I didn't like the oversized look on me. Still a nice shirt! Size 12 (XL)
Coolane Women's Oversized Graphic Long Sleeve Jersey T-Shirt - White Sportswear
Bottoms
SHEIN Pleated Skirt | My fave pleated skirt so far! I ordered a size 12 (0XL) and it was a tad bit big so maybe size down.
SHEIN EZwear Plus Size Summer Sexy Solid Color Pleated Mini Skirt
SHEIN Black Jeans | Very stretchy but because there's no top button, the zipper can come down if your bloated or if they're too tight for you so make sure you get your correct size. I got a size 14 (XL)
SHEIN ICON Plus Size Distressed Slim Fit Flare Leg Jeans - Shop Now
Shein Warm Leggings | VERY warm and stretchy with added tummy control. Size 12 (0XL)
2-Piece Plus Size Thermal High-Waisted Leggings for Winter Workouts
SHEIN Mesh Pants | 100% see through so if you're not comfortable with the your backside being exposed, either wear shorts under or don't purchase. LOVE these so much and they're stretchy. Very sexy for a club night out! Size 14 (XL)
SHEIN Slayr Plus Size Women's Velvet Sheer Tights - Shop Now
Bodysuits
SHEIN Bodysuit | I absolutely LOVED this jumpsuit. It snatched me up and really accentuated my curves. HOWEVER, only after wearing it 2-3 times, the zipper broke. Size 12 (XL)
Zip Up Unitard Jumpsuit - SHEIN USA
Shoes
SHEIN Knee High Boots For Plus Size | Perfect Prada boot dupe and BIG CALF FRIENDLY! Size US 9.5
Women's Comfortable Platform Knee High Boots - Classic Style Fashion Footwear
SHEIN Plus Size Heel Boots | Perfect Shark Boot dupes and BIG CALF FRIENDLY (however you might need help getting these off. Also they do slip a bit if your calves are bigger so you may walk on the back of the folded over piece) Size US 9
SHUZIA Women's Beige Suede High-Heeled Boots - Everyday Casual Comfort