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And don't even get us started on your date's attire

Even the most stylish people can fall into a fashion rut during winter because it's tempting to throw on the coziest possible outfiteven if you wore it days ago

Advertisement - Continue Reading Below 7 Startraks Proving there was never such thing as too much pleather, Jessica Simpson really went for it in a head-to-toe red hot look

Almost everyone who grew up in that era can remember the types of sneakers their dad wore: big, chunky sneakers in either highly neutral or oddly colorful palettes, oftentimes leather, mesh, or some hybrid of both usually from New Balance or a similar brand

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Chunky and embellished sneakers took center stage, featuring thicker soles and a bulkier aesthetic rarely seen in contemporary styles