UGGs and Maxi Dresses: A Style Combo That Works

Many women feel stuck in a style rut the moment temperatures drop. Jeans, jumpers, rinse, repeat. The idea of wearing a maxi dress in winter feels daring, and pairing it with UGGs? That sounds downright wrong… until you see it styled right.

And that’s exactly what this article is here to show you.

We’ve seen this unexpected combo go from “What are you wearing?” to “Where’d you get that look?” With the right shapes, styling, and a bit of balance, you can make UGG boots and maxi dresses your go-to outfit, not just a desperate last-minute choice.

In this guide, you’ll learn how to make this pairing work, from choosing the right type of dress to styling tips that make the whole look intentional. No more guessing games. No more second-guessing yourself in the mirror.

Let’s get into it.

Why UGGs and Maxi Dresses Can Actually Work

At first glance, UGG boots and dresses feel like opposites. One’s chunky and built for warmth, the other’s flowy and often worn in warmer weather. But here’s the thing: contrast is where style lives.

When done right, pairing something soft and slouchy (like a classic UGG boot) with something long and drapey (like a maxi dress) creates a balance that’s both relaxed and elevated. It’s giving. I just threw this on, but in a way that feels fresh, not careless.

Here’s why the combo works:

Contrast Makes It Interesting.

UGGs add weight to the bottom of your outfit, which can ground a light, airy maxi dress and keep it from feeling too summery or floaty.

It mixes seasons, and that’s very now.

Layering warm and cool-weather pieces is a styling trick used everywhere from street style to fashion runways. It’s practical and visually appealing.

Comfort Is The New Cool.

The rise of “lazy luxury” and effortless dressing means you can prioritise comfort without sacrificing style. UGGs are no longer just house shoes, they’re a fashion statement when styled well.

It Breaks The Rules — In A Good Way.

This combo turns heads because it’s unexpected. And when you own it, it looks intentional and confident, not like a mismatch.

So yes, you can wear UGGs with a maxi dress. The key? Knowing how to choose the right kind of dress, and that’s what we’re diving into next.

What to Look for in the Right Maxi Dress

Not all maxi dresses play nicely with UGG boots. If you want to avoid looking like you’re wearing your dressing gown out to the shops, the secret lies in choosing the right dress silhouette, fabric, and overall vibe.

Here’s what to look for:

Heavier Fabrics Work Best

Floaty, ultra-light fabrics like chiffon or thin rayon can clash with the chunkiness of UGGs — they create too much contrast and end up looking seasonally confused. Instead, go for:

• Ribbed knits

• Cotton jersey

• Sweater dresses

• Waffle or thermal textures

These feel more autumn/winter-appropriate and pair naturally with the softness of UGGs.

The Right Length Matters

Aim for a dress that hits just above the ankle or slightly grazes the top of your UGGs. Anything that drags too low will bunch awkwardly or hide your boots altogether. Midaxi lengths can also work well with shorter UGG styles.

Consider the Shape

Avoid anything too billowy or oversized from top to bottom — this can overwhelm your frame and make the outfit look sloppy.

Instead, try:

• Fitted or A-line shapes

• Wrap styles

• Shirred waists or belted options

These give your body some shape and help balance out the volume of the boots.

Slits Help

A side or front slit breaks up the length of the dress and gives a peek at your boots — which keeps the outfit from looking too heavy or closed-in.

Stick to a Neutral or Earthy Palette (or Go Monochrome)

If your UGGs are classic tan, chestnut, or black, choose dresses in earthy tones, muted colours, or tonal hues. A monochrome look can also make everything feel sleek and put-together, even if the pieces themselves are casual.

Types of UGGs That Pair Best

Let’s be honest — some UGGs are made for the couch. Others? Surprisingly chic when styled right. If you want your UGGs and maxi dress combo to look intentional (and not like you just popped out for milk in your pyjamas), choosing the right UGGs is key.

Here’s what works best:

UGG Minis and UGG Premium Ankle Boots

These are your MVPs. They’re less bulky, hit just above the ankle, and create a nice visual break between the hem of your dress and the boot itself. They look especially good with dresses that show a little leg through slits or side seams.

Style tip:

Pair Classic Mini UGGs with a belted knit dress and a cropped jacket for a cosy, balanced look.

Platform UGGs

If you want height and comfort, platform UGGs are where it’s at. They give your maxi dress that little lift, which helps prevent it from dragging — plus they add a bit of edge to the overall look.

Style tip:

A fitted maxi with a side slit and platform UGGs gives a comfy-meets-cool streetwear vibe.

Classic Short UGGs

These are trickier but not impossible. They’re bulkier and can visually shorten your legs if not balanced properly, but if your dress is more fitted or you’ve got a good coat to anchor the look, they can still work.

Style tip:

Stick to neutral dresses and consider layering with a structured coat to keep the outfit from feeling too soft or slouchy.

Styling Tips to Pull the Look Together

So, you’ve got the right maxi dress and a pair of UGGs that don’t look like they belong solely in your lounge room. Now it’s time to pull everything together so the outfit looks styled, not accidental.

Here’s how to do that:

Layer Up Top

A maxi dress and UGGs alone can feel a little undone. Adding a structured or textural layer helps balance the softness of the outfit.

Try:

• Cropped puffer jacket — adds volume up top and keeps proportions in check.

• Denim or faux leather jacket — gives edge and contrast.

• Oversized knit cardigan or shacket — soft on soft, but intentional when layered right.

Pro tip:

Balance is everything. If your dress is flowy, go more structured with your outer layer. If your dress is fitted, oversized outerwear can work beautifully.

Add a Waistline

• If your maxi dress doesn’t already define your waist, you can create shape using:

• A belt over the dress

• A cropped jumper layered on top (tuck it under a bra or use a hair tie hack for a cinched waist

This helps break up the outfit and keeps you from looking like one long column of fabric.

Go Hard on Accessories

• Accessories elevate any outfit, especially one built on basics.

• Crossbody bags or mini backpacks add structure.

• Chunky UGG scarves or beanies help bring in texture and pull colours together.

• Sunglasses can make even the cosiest outfit look chic.

Style trick:

Match your accessories (like your beanie or bag) to the colour of your UGGs or your dress — it creates cohesion without trying too hard.

Roll or Cuff If Needed

If your dress has sleeves that feel bulky or a hem that’s just a bit too long, a roll or knot can help. Knotted hems can add shape and allow your boots to peek through more.

Occasions This Outfit Actually Works For

Let’s be real: not every outfit needs to be red carpet-ready. Some just need to feel good, look good, and work for your actual life. The UGGs + maxi dress combo? Surprisingly versatile when styled right.

Here’s where you can wear it with confidence:

Brunch or Coffee Runs

Comfy, low-effort, and still put-together — this outfit is made for casual catch-ups. Pair it with a crossbody bag, sunglasses, and a beanie for a relaxed weekend vibe that still looks styled.

School Drop-Offs or Errands

You’re out the door in five minutes but want to look like you didn’t just roll out of bed. UGGs and a maxi dress, topped with a warm coat, gets the job done while keeping you cosy and polished.

Airport Travel

UGGs are practically made for airport security. Combine them with a knit maxi dress and layers that are easy to peel off, and you’ve got a travel look that’s stylish and sleep-ready.

Casual Work Days

If your workplace leans casual or you work remotely and like to dress for productivity, this combo ticks the box. Keep the dress more tailored and go for a sleek pair of UGG Minis or platforms. Add a structured blazer and you’re golden.

Low-Key Date Nights

A body-hugging maxi with platform UGGs and a faux leather jacket? That’s an “I didn’t try too hard, but still nailed it” kind of look. Add hoops and a small bag and you’re ready.

You Can Absolutely Pull This Off

Let’s be clear — wearing UGGs with a maxi dress isn’t just allowed, it’s a clever, comfy style move when you do it with intention. It’s proof that you can feel warm without looking weighed down, and that comfort doesn’t have to mean sacrificing style.

Remember: fashion rules are meant to be broken — especially when the result is a laid-back, modern outfit that works for real life. With the right dress, the right boots, and a few simple styling tricks, this look becomes less about “Can I pull this off?” and more about “Why haven’t I done this sooner?”

So go on, pull out that maxi, slide into those UGGs, and own it. You’ll not only look good, you’ll feel like yourself, and that’s the best style move you can make.

Head over to our UGG Originals store to shop Australian-made UGGs that are as stylish as they are comfortable. Whether you’re after Minis, Ultra Minis, or elevated platforms, you’ll find the perfect match to pair with your favourite maxi.