A Definitive Guide To Pairing Dresses With Boots and Bare Legs

- 1/29
Less than a month out from fall’s calendar-official start, the air’s settled into a glorious not-too-hot, not-too-cold place of sunny briskness — or as we like to call it, dress and boot temperature. Still bare leg-friendly conditions, but (finally!) cool enough to ditch those summer sandals you are so over, it presents a rare moment in the season when you can solely focus on fun ways to mix and match the two pieces without dealing with an extreme forecast’s limitations. There’s no fussing over how tights and puffer coats factor in; you needn’t limit yourself to light, ventilated fabrics.
The only thing you’ve got to worry about is finding fresh and interesting ways to spin the combination, like the five celeb-inspired ideas in the slides ahead. To make your AM routines easier in the next few golden weeks of 60 degree days, we’ve shopped each pairing out — along with every other piece needed to complete the look — and broken down exactly why it’s so great. Not that we’ve done all the work, of course: it’s still on you to place the order.
- 2015 Bauer-Griffin2/29
Anchor a feminine midi wrap with tall suede boots.
Successfully wearing a long floral number past summer boils down to your footwear choice. Hailey’s subtly Western inspired boots (read: no tooling or embroidery — too literal!) here offer the perfect solution: autumnal enough to balance out the floaty, warm weather feel of her dress, while providing extra insulation against cold snaps. To follow the boho romantic direction she’s taken this outfit, layer in some turquoise and silver jewelry and, on especially crisp days, a long belted cardigan in a chunky knit.
- 3/29
Ralph Lauren floral wrap fress, $145. ralphlauren.com
- 4/29
Sigerson Morrison gonna suede knee boots, $695. shopbop.com
- 5/29
__ Vanessa Mooney__ good chain wrap necklace, $40. threadsense.com
- 6/29
ASOS festival enamel drop earrings, $9. us.asos.com
- 2014 Marc Piasecki7/29
Use punky black booties to give your LBD some edge.
Not all little black dresses fall in pearl-and-tiara, Breakfast At Tiffany’s territory. To make yours more rock concert than cocktail party, do like Kylie, and pair an abbreviated hemline with stacked heel ankle boots. A slightly oversized moto jacket (bonus points for metallic embellishment!) and bag with exposed hardware — both, naturally, in the same noir shade — drive the point home.
- 8/29
Topshop textured a-line dress, $75. us.topshop.com
- 9/29
Zara embroidered jacket, $149. zara.com
- 10/29
Jeffrey Campbell arundel boots, $190. us.topshop.com
- 11/29
She + Lo next chapter mini satchel, $248. shopbop.com
- 12/29
Ray-Ban rimless large aviator sunglasses, $160. bloomingdales.com
- 2015 Noel Vasquez13/29
Enjoy the snuggly sophistication of a sweater dress and over-the-knee boots.
Hey, we get it: Some mornings all you really want to wear is a giant, Snuggie-like pullover. To pull it off in the most polished way possible, follow Kendall’s lead by working in thigh-high boots. Balanced by the slouchy, oversized fit on your top half, the footwear will feel far less aggressively come hither than usual; think less sultry, more sophisticated. Even better, because the two silhouettes keep your body completely covered, you can rely this formula straight through winter (when it get especially frigid, though, layer in tights).
- 14/29
Aritzia bianca dress, $175. aritzia.com
- 15/29
ALDO haskova boots, $220. aldoshoes.com
- 16/29
Banana Republic mini drawstring crossbody, $128. bananarepublic.com
- 2015 Daniel Zuchnik17/29
Dress up a button-front tunic with stacked heel booties.
Even a light cotton shirtdress can work through mid-fall with the right accessories. Sturdy ankle boots are a fail proof place to start, laying the foundation for a thick leather belt and fur-trimmed jacket. Although we love the way Bella’s stuck to just one shade here, there’s a countless number of other color schemes that suit this look. A few of our favorites to get you started: white and tan, navy and black, warm grey and cream.
- 18/29
Madewell moviehouse shirtdress, $138. madewell.com
- 19/29
Dolce Vita ginnee booties, $200. dolcevita.com
- 20/29
Mango aviator zip jacket, $200. mango.com
- 21/29
H&M leather belt, $13. hm.com
- 22/29
Ela M.I.L.C.K. star handbag, $438. clubmonaco.com
- 2014 Gilbert Carrasquillo23/29
Make a micro shift more casual with chunky oxford booties.
Between the low practical heel, and menswear-inspired design, a pair of lace-up ankle boots act as a no-nonsense counterpoint to a micro mini’s party-ready length. Keep this push-pull effect going by tossing on a floor length overcoat — always left open, however, so you can see the contrasting proportions — funky round sunglasses, and cross-body in a striking color. That one touch of brightness instantly ties the whole ensemble together.
- 24/29
Helmut Lang sleeve crepe dress, $495. matchesfashion.com
- 25/29
Rachel Comey ibex booties, $426. rachelcomey.com
- 26/29
Topshop longline slouchy coat, $170. us.topshop.com
- 27/29
Rebecca Minkof micro noto satchel, $195. shopbop.com
- 28/29
River Island black round sunglasses, $26. us.riverisland.com





























