7 Dress-and-Boots Outfits That Look Good Every Single Winter

As soon as there's a sign of winter (even the subtlest one), I'm quick to pull my favourite boots out from hibernation, throw on a floral dress and get outside fast. Over the past week or so, the weather has been perfect for boots, bare legs and wearing a dress sans coat or jacket. So what do last year's over-the-knee boots work best with? How can you wear your trusty white ankle boots best in this last half of 2018? And are Western boots more than a one-season wonder?
A few years ago, the boot market was quite limited: combat boots, black ankle boots and the occasional pair of OTKs were the norm. These days, you have more styles on offer than ever before. Not only are there more boots on offer but there's also an array of new dresses out there. That being said, exciting new outfit formulas are being presented on the streets and on our Instagram feeds. Keep reading to see dress-and-boot outfits that look effortless and current.
Prairie Dress + Western Boots
Shop the look:
Printed Dress With White Accents + White Ankle Boots
Shop the look:
Long Dress + Combat Boots
Shop the look:
LBD + Black Knee-High Boots
Shop the look:
Tonal Dress + Boots
Boho Dress + Slouchy Boots
Shop the look:
Midi Dress + Snake-Print Knee-High Boots
Shop the look:
Next up, the other winter outfits you can rely on.
This story was published at an earlier time and has since been updated.

Hannah Almassi is the Editor in Chief of Who What Wear UK. She joined in 2015 when she launched the UK sister site following a seven-year tenure at Grazia magazine as fashion news and features editor. With experience in print and digital across fashion and beauty, Hannah has over 18 years of experience as a journalist, editor and content strategist. Her opinion has been sought by the likes of CNBC, BBC, The Sunday Times Style, The Times, The Telegraph and MatchesFashion.com and she is often called upon for her take on trends, becoming known as a person with their finger of the pulse of what’s happening in the fashion space for stylish Brits.
-
Whenever I'm in Paris, I See This Boot Trend Styled With Minidresses in Every Vintage Shop and Local Bistro
Sorry, ankle boots, but it's not you.
-
Everyone in Los Angeles Knows This Shoe Trend Makes Denim Shorts Look Way Cooler
Denim shorts never looked so good.
-
Spotted at Wimbledon: The Anti-Summer Shoe Trend You Don't Usually See in the Stands
Never too hot for these.
-
The $140 Boots London Fashion Girls Take Out of Storage Every Summer to Wear With Shorts and Dresses
From Kate Moss to Daisy Edgar-Jones.
-
Stop With the Ankle Boots—Miniskirts Should Only Be Worn Like *This* in 2025
Period.
-
The Unexpected Shoe Style Fashion People Are Reaching For This Summer
Here are seven ways to wear it.
-
Oh, Hello! Meet the New It Ugg Boots You'll Spot on Fashion People and Celebs
These are about to be everywhere.
-
Return Those New Flats—*These* Are the Cool Shoes Fashion People Are Wearing With Dresses and Skirts
Fresh and unexpected.