12 Fresh Ways to Wear Your Dresses With Boots This Winter

With the colder weather here (and sticking around), you've probably spent some time thinking about cosy outfit formulas over the last few weeks. You know, the looks that will keep us warm and looking chic? And one look we've learned to fall back on for this is dresses with tights and boots. The simple combination makes for an easy way to take your warm-weather pieces into a new season altogether. With the addition of tights and boots, even the floatiest slip can work under the right circumstances.

So today, we’re highlighting a number of cool and fresh ways to wear your favourite dresses with tights and boots. Some work for seriously chilly temps while others are better reserved for slightly warmer wintery weather. Still, no matter what the day may look like outside, you're guaranteed you'll find some easy dress, tight and boot outfit inspiration below. 

1. Printed Dress + Ankle Boots + Bright Sweater

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(Image credit: The Style Stalker)

Style Notes: A floaty, printed dress layered with a bright sweater and black boots is an easy way to add some fun to your winter wardrobe, without compromising on warmth. Bonus points if you add some seriously cool accessories.

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2. Floral Dress + Riding Boots + Black Tights

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(Image credit: The Style Stalker)

Style Notes: Equestrian-style boots add a cool contrast against a vintage-inspired floral dress. Add a cosy teddy coat for chilly winter days. 

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3. Animal Print Dress + Chunky Boots + Fun Tights

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(Image credit: @champagnemani)

Style Notes: Change up your tights game and opt for a fun print to pair with a clashing dress. Maximalists, this one is for you. 

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4. Blazer Dress + Knee-High Boots + Sheer Tights

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(Image credit: The Style Stalker)

Style Notes: Flat knee-high boots are the perfect choice when paired with a mini dress and tights. You can also swap heeled knee-highs for the evening, too.

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5. Knit Dress + Coat + Tall Boots

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(Image credit: @francescasaffari)

Style Notes: Pair a cosy knit dress with a longline coat for a look that just works. Of course knee-high boots and tights are basically an essential with this look at this time of year.

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6. Printed Knit Dress + Clashing Coat + Thick Tread Boots

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(Image credit: @greceghanem)

Style Notes: Opt for lots of cool layers in mixed prints to add interest to your boots and dress ensemble. Fleece-lined tights underneath this keep it cosy.

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7. Slip Dress + Cardigan + Snake Print Boots

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(Image credit: The Style Stalker)

Style Notes: A tonal look always looks so sleek and sophisticated. Add sheer or 20-denier tights to this before topping it off with a shearling jacket.

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8. Black Dress + Leather Jacket + Suede Boots

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(Image credit: The Style Stalker)

Style Notes: An all-black ensemble always looks so luxe with a pair of tan suede tan boots. Add a biker for a touch of edge.

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9. Leather Midi Dress + Roll-Neck + Ankle Boots

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(Image credit: @thandimaq)

Style Notes: Layering is the key to winter dressing, and Thandi has nailed it by adding a roll-neck under a leather shirt dress. So effortless. 

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10. Knit Dress + Blazer + Knee-High Boots

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(Image credit: @sasha.mei)

Style Notes: Naturally we love this knit dress and blazer loo, which can be dressed up or down with a simple swap of accessories, too. 

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11. Printed Mini Dress + Platform Boots

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(Image credit: @juliesfi)

Style Notes: Platform boots (yep, they're back) with a pretty printed mini dress is an unexpectedly cool way to wear the trend.

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12. LBD + Sock Boots

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(Image credit: @rosiehw)

Style Notes: If you're off to a brunch or knit out, the equation of a LBD dress with tights, sock boots and a cosy coat on top always works. 

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Next Up: Spring/Summer 2023 Fashion Trends: The 21 Looks You Need to Know About

This piece originally appeared on Who What Wear U.S at an earlier date and has since been updated.

Judith Jones
Senior Fashion Market Editor

Judith is the senior fashion market editor at Who What Wear and has worked in fashion for nearly a decade. Judith started on the Shop Who What Wear team, creating content and managing a team of merchandisers for the Who What Wear shopping app. She later crossed over to the editorial team, where she shares the coolest, most desirable fashion market finds and brands in her shopping-focused stories and social takeovers. She has become one of the top affiliate earners during her six plus years at Who What Wear. Before working in fashion, Judith was a TV host on the PBS travel show Globe Trekker (airing on Netflix and Amazon Prime) and shared her passion for travel and food. She studied at the prestigious London Academy of Dramatic Arts as well as Stella Adler Studio of Acting in New York. She later studied fashion merchandising and design, which laid the foundation for her career in fashion.


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