For today's Get Dressed With Merrick I'm going to walk you through a few looks and tips to wearing a dress with boots. 1. For a more casual look, try a Chelsea boot with your dresses. I love Chelsea boots so much, and they're a great option for fall and winter with dresses. They're more casual, don't have a heel, and keep your feet warm.. Keep it subtle with just the thighs on display. Instagram. If you don't want the stockings to be your outfit's main focus, pairing them with boots is your best bet. The taller the boot, the better. Knee-high and thigh-high boots leave just a sliver of your upper legs revealed where your tights will shine through.

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Best Dress to Wear With Chelsea Boots: Steve Madden Crissy Long Sleeve Dress. Frankly, you can pair this Steve Madden Crissy Long Sleeve Dress ($47, originally $79) with really any style of boot.. BTFBM Women's Square Neck Smocked Dress. This floral blue option from Amazon will pair well with tights and a low boot for a stylish fall look. Yes, even Amazon has worthy dresses to wear with tights. The BTFBM Square Neck Smocked Dress, which is sold in women's sizes S to XXL, features a tiered skirt, smocked bodice, and balloon sleeves, all.