Can You Wear UGG Boots on a City Holiday?

You’ve booked the flights, planned the must-see stops, and started mentally packing outfits. But there’s one piece you’re not quite sure about: your short UGG boots.

They’re cosy, they’re reliable—but can they really handle the streets of Melbourne, Tokyo, or New York without screaming “I just rolled out of bed”?

Absolutely. And here’s the thing: you don’t have to choose between comfort and style.

UGG boots have come a long way from being the go-to shoe for lazy Sundays. The right styling can take them from loungey to luxe, making them a surprisingly versatile pick for your urban getaway.

I’ve helped style city travellers who want that perfect middle ground: shoes they can walk in all day and still feel put-together in when they stop for dinner or drinks. In this article, you’ll get easy outfit ideas, weather-specific tips, and ways to dress your short UGG boots up or down—without overpacking.

By the time you finish reading, you’ll know exactly how to work your short UGGs into your urban holiday wardrobe without sacrificing an ounce of style.

Why Short UGG Boots Deserve a Spot in Your Suitcase

When you think “urban style,” UGG boots might not be the first thing that comes to mind. But short UGGs? They’re in a league of their own. These aren’t just winter warmers or lounge-day staples—they’re a smart travel move for city explorers who care about comfort and style.

Let’s start with the basics. Short UGG boots, like the Classic Short range from UGG Australia Classic, are:

• Lightweight and easy to pack – They won’t eat up your whole suitcase.

• Effortlessly comfortable – That soft sheepskin lining cushions every step on pavement, cobblestones, or wherever your itinerary takes you.

• Weather-friendly – Treated versions are water-resistant and can handle light rain or chilly mornings.

• Style-flexible – Their shorter profile makes them less bulky and easier to pair with city-ready outfits compared to the tall classics.

Short UGGs also toe the line between casual and elevated. You can dress them down with leggings and a hoodie or dress them up with a trench and slim-fit jeans.

Daytime Chic: Casual Sightseeing Outfits

City exploring means one thing—you’ll be on your feet a lot. Whether you’re wandering laneways in Melbourne or hopping from gallery to café in Berlin, you want an outfit that’s functional but still looks put-together in photos.

That’s where short UGG boots shine. Their sleek silhouette makes them easy to work into an off-duty city look, and that plush lining means your feet won’t hate you after hours of walking.

Here are a few easy outfit ideas to get you started:

Leggings + Oversized Knit + Crossbody Bag

This is a no-brainer combo for travel days or casual strolls. Choose black leggings (bonus points for leather-look), a chunky jumper, and a compact crossbody to keep things effortless. Finish with short UGGs in chestnut or black and you're golden.

Straight-Leg Jeans + Tucked Tee + Long Coat

This look is polished without trying too hard. A tucked-in tee keeps it clean, and a longline coat adds that city-cool edge. Throw on your short UGG boots for contrast—casual meets chic.

Midi Skirt + Fitted Turtleneck + Denim Jacket

Yes, you can wear a skirt with UGG boots. Choose a neutral midi skirt, a fitted top to balance the proportions, and a cropped jacket. Add a beanie or bold sunglasses to tie it together.

Matching Co-ord Set + Short UGGs

A comfy tracksuit set instantly looks more intentional when it matches. Choose earthy or muted tones and add gold hoops or a sleek backpack to elevate it. Perfect for airport-to-city transitions.

The goal with daytime styling is to blend comfort with a bit of edge. Don’t be afraid to mix textures—think denim, knits, and leather—and lean on accessories to take things up a notch.

Evening Elegance: Transitioning to Nighttime Looks

Let’s be real—when you’re on holiday, you don’t want to head back to the hotel just to change outfits. You want shoes that can take you from day to night without needing a second pair. And yes, short UGG boots can absolutely do that.

The trick is in the styling. It’s all about elevating the rest of your outfit so your UGGs look intentional—not like an afterthought.

Here’s how to pull it off:

Black Short UGGs + Slim Trousers + Blazer

This combo is sleek but still comfortable. Choose cigarette pants or ankle-grazing tailored trousers, a fitted knit or blouse, and top it with a structured blazer. Short UGGs in black keep the look cohesive while softening the sharp edges—perfect for dinner or drinks.

Monochrome Base + Statement Coat

Wearing one colour head-to-toe (like all black or all beige) instantly makes an outfit feel dressier. Add a statement coat—think faux fur, a bold colour, or a classic trench—to elevate the whole look. Your short UGG boots will blend in seamlessly.

Sweater Dress + Tights + Belted Waist

A knitted dress is your best friend here. Cinch the waist with a belt, add tights and a longline coat, and finish with your short UGGs. It’s a cosy yet sophisticated outfit you can wear to a show, a wine bar, or a late-night walk along the river.

Midi Skirt + Button-Up Shirt + Leather Jacket

This mix of structured and soft elements creates a balanced, city-ready look. The leather jacket brings the edge, the skirt brings the polish, and your short UGGs keep it grounded and wearable.

Pro tip: Stick to neutral or darker shades of UGGs at night—black, chestnut, or grey work best for evening wear because they blend more easily with elevated pieces.

Weather Considerations: Styling for Rain, Chill & Sunshine

One of the best parts about short UGG boots? They’re surprisingly adaptable to whatever the weather throws at you. Whether you're dealing with crisp autumn mornings, unexpected drizzle, or that in-between-season chill, they’ve got your back (or feet, in this case).

Here’s how to dress around your UGGs depending on the weather forecast:

Light Rain

Short UGGs like the Classic Short II from UGG Australia Classic come pre-treated with water resistance, so they can handle light showers and wet pavements. Pair them with cuffed jeans, a water-resistant trench, and a bucket hat or cap. Steer clear of deep puddles and you're golden.

Cold Mornings & Cool Afternoons

This is where UGGs really shine. That genuine sheepskin lining keeps your feet warm without overheating. Try layering a thermal long sleeve under a jumper, add a puffer or wool coat, and finish with a beanie and scarf. Opt for dark skinny jeans or leggings to balance out the soft, chunky vibe of the boots.

Mild & Sunny

Yes, you can still wear UGGs on a sunny day. Choose lighter colours like chestnut or sand and pair them with a floaty midi skirt or light-wash denim. Swap your coat for a denim jacket or oversized shirt and keep accessories minimal. It’s a perfect in-between look for city strolls or brunch stops.

Windy Weather

Stick to slim silhouettes so the wind doesn’t take over your outfit. Leggings or skinny jeans, a turtleneck, and a belted coat work well. Add a structured bag and pull your hair back or wear a cap to stay fuss-free.

UGG Sheepskin Accessories: The Ultimate Cozy Add-Ons

UGG isn’t just about boots—sheepskin accessories bring the same signature warmth, softness, and style to your everyday essentials. Whether you're braving chilly weather or just looking to elevate your cozy wardrobe, the right accessories can make all the difference.

Sheepskin Gloves & Mittens

Keep your hands toasty while maintaining effortless style. UGG sheepskin gloves offer natural insulation, ensuring warmth without bulk. Whether you're running errands or enjoying a winter stroll, these gloves provide a perfect balance of function and fashion.

Sheepskin Hats & Ear Warmers

Complete your cold-weather look with a UGG hat or ear warmers. The plush interior keeps you warm, while the classic design pairs effortlessly with any outfit. For a timeless winter look, match your hat with your UGG boots for a coordinated ensemble.

Sheepskin Insoles

Upgrade your comfort with sheepskin insoles—perfect for refreshing your favorite UGG boots or adding extra warmth to other footwear. These naturally temperature-regulating inserts keep feet cozy in winter and cool in summer, making them a must-have for year-round wear.

UGG Wool Scarves: The Effortless Finishing Touch

Your outfit’s not complete without a little something extra—and a wool scarf does the job perfectly. The UGG wool scarf collection is all about that signature softness, but with a polished, urban twist.

Crafted from premium Australian wool, these scarves aren’t just warm—they’re stylish, breathable, and versatile enough to pair with every outfit in your suitcase.

Here’s how to wear them with your short UGG boots:

• For a relaxed day look: Loop a neutral-toned scarf over an oversized coat or puffer for a soft, layered effect.

• For a dressier outfit: Drape a fine-knit wool scarf over your shoulders with a tailored blazer or longline trench. It adds instant texture without bulk.

• For in-between weather: Tie a lightweight wool scarf loosely at the neck with a knit jumper and jeans—simple, effortless, and just warm enough.

Find Your Perfect Pair of Short UGG Boots

So, can you wear short UGG boots on an urban vacation? Absolutely—and now you know how to do it with style.

From coffee runs to rooftop cocktails, sightseeing sprees to last-minute dinners, your UGGs can carry you through the day (and night) with ease. The key is intention—pairing comfort with structure, softness with edge, and function with fashion.

You don’t need to pack three different pairs of shoes to feel prepared. Just one thoughtfully styled pair of short UGG boots, some versatile outfit combos, and the right accessories—and you’re set for whatever the city throws at you.

If you’re looking to style your urban getaway with comfort and confidence, a pair of Classic Short UGG Boots is the perfect place to start.

Explore the full range of colours and styles over at UGG Shop of UGG Australia Classic—and find the perfect pair to take on your next city escape.