It’s Dresses with Boots Season: The Best of the Bunch

While many retailers are whipping out spring clothing, most of us are the most bundled up they will be this winter. For me, it's dresses with boots season. Skirts that go below the knee but won't spill into slush, that work with durable tall boots, and under those boots may be leggings, fleece or wool tights, thick socks, long underwear, or a combination no one else knows because they're distracted by the pretty dress.

Boots right now are on sale and a good item to purchase if you don't already have some. They won't be going out of fashion any time soon, and if you buy either really interesting and fun or really basic and classic but always of quality materials, you'll get years and years of wear from them. These are my picks for stylish wide calf boots. Take them to a cobbler at the end of boot season to be reheeled, resoled, and repaired so they're ready come next fall.

Made from machine washable viscose, winterize this dress with a lightweight turtleneck, thick socks, and boots. Come spring, pair it with shorter boots or even sneakers. Real buttons all the way down the front, you can customize your silhouette. Sizes XS-4X with petite and tall.

Machine washable 58% cotton, 39% modal, and 3% elastane, this is a versatile dress that can go from desk to drinks, work to weekend, fall to winter to early spring. Sizes 1X-3X; the dress is available at this link in sizes XXS-XXL and this link in petite XS-L.

Dress up while staying warm with this machine washable chiffon overlay dress. Style with tall boots, tights, and an insulating base layer for elegance with comfort. Sizes 2-18.

This printed and ribbed sweater knit dress just brings a smile to my face. Made from 65% viscose/35% polyamide, wear over a crisp white shirt, a tissue-weight turtleneck, under a denim jacket or a belted jardigan, with boots and tights, or come spring with flats or sneakers. I love putting these slip dresses under dresses like this for invisible warmth. Sizes XS-XL; in case it sells out it's also available same price and size range at this link.

Another dress you can layer for warmth yet wear into late spring and early summer with a change of footwear. This denim utility dress would look great over a fitted turtleneck or long-sleeved crew, stylish with tall boots or ankle booties, and get springy with wood heel sandals and a raffia tote. Sizes 2-14.

The belted wrap design makes this sweater dress stand out from the crowd and create a unique detail that transcends trends but adds chic style. Made from 55% extra-fine merino wool and 45% organic cotton it needs to be babied a bit more than the dresses above, but you may find the work worth it for the cool design. Sizes XXS-XXL and petite.

Battle the winter grays with a bold floral. This floral shirtdress has a full button placket, pockets, is machine washable viscose, and has a stylish bow tie you can play with for different looks. This would look great over a fitted turtleneck or open the neckline to show a striped fitted crew. This is totally a three-season dress and I love how it was styled with colorful boots, though black would also be chic. Sizes 12/14 – 32/34.

Have fun with winter fashion and embrace the polka-dot trend with this satin sheath. Layer it with a blazer, wrap sweater, or cropped sweater, style with boots, and then dress it up another time with satin ballet flats and a sparkly necklace. Try it with an obi belt, or tie a scarf on the diagonal around the waist. Dickies are back; this would look great with a frilly white collar. Made from 98% Viscose and 2% Spandex, this dress is machine washable, the fabric is three season, and you'll be surprised how many different ways you can style what at first glance looks like a one-off piece. Sizes 00-18 and petite.