Pairs my go to of a comfy top with skinny jeans, but with details I don't yet own...a comfy plaid top is awesome in theory, don't have one yet, and the detail on the skinny jeans is pretty neat! Boots are also awesome, I have a similar gray pair.
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I would wear this for my date night because I would be showing off my beautiful short tan legs, lol, but they would look longer in those cute wedges! & I love the combination with the wallet/purse with the necklace & black dress.