Winters without boots? Not a chance. Whether it's a café or the streets, it’s the time when boots are everywhere, and one such style that is quite popular is ankle boots. These booties work magically and can transform any boring outfit into a statement style in no time. But styling them can be a little tricky; that’s exactly why we are here – to help you master the ankle boots look.
Our Top Picks
Ankle boots with Jeans - Casual Everyday Look
Ankle boots and jeans are one of the easiest combos to try with. No matter what the plans are, this duo will definitely work. Whether it's Chelsea or chunky combat, there are numerous styles to pair up with jeans.


But styling them needs focus on minor details. First and most important, there should be a flattering visible gap between your jeans and the hem of your boots - 1 to 2 inches at least. For this, choose cropped jeans or simply cuff your regular ones.


On the other hand, skinny jeans work differently. They look best when tucked into your boots, while wide-leg and baggy jeans will go over them. Moreover, always maintain a balanced proportion – the wider the jeans, the sleeker the boots should be, that’s the key.
Our top Fit Picks
Everyone loves denim, but styling with ankle boots is not that simple. You can try pairing them with a white sweater and layer up with a tan coat. Complete the style with leather ankle boots.
- While having a brunch at your favorite restaurant, style up your jeans with a V-neck sweater. You can layer this with a long coat and classic Chelsea boots.
- For dressing up for a night hangout, skinny jeans with a white crew neck look really nice. Adding an olive jacket gives a perfect look. Pair up brown chunky boots to complete the style.
Ankle Boots with Dresses - Sweet & Feminine
Dresses in winter? Why not! Don’t let go of this adorable combo style just because it's cold outside. You can pair them with leggings and coats to stay toasty. In fact, this beautiful combination can work magically for different settings.


What makes this combo worth considering is its versatility. From grocery runs to dinner plans, it just beautifully adapts to wherever you go. Additionally, they look absolutely stunning and work around the year without any fuss.

When styling these two, consider the vibe, too. If you think of twirly floral dresses, go with suede boots; likewise, for a modern look, style structured dresses with leather boots. Also, don’t forget about the hemline – it should end a few inches above the boots.
Fits that make sense
- For romantic dinner plans, a navy silk midi dress with brown stiletto-heeled pointed boots looks just great.
- Love florals? Pair up a red floral flowy dress with western ankle boots, and you are good to go.
- Night calls out – a burgundy maxi dress would be a great choice. Pair this up with chunky boots. Wrap the hair into a bun to look a bit fancier.
Office-ready vibe with a fun
If you live in a country that always gets cold, then ankle boots are a must. And the most interesting part? Super versatile, in the blink of an eye, you go from work to lazy mode. These boots work really well with both settings. All you need is a cashmere coat or a biker jacket to switch with a blazer. Next, loosen your bun, and you are all set to rock the after-work fun. Whether it's movies or dinners, these boots wont let you down.

While selecting these booties for office wear, stick to warm and soft colors. Whether it's a suit or a formal skirt look, ankle boots can go with a lot of outfits. Also, keeping the heels low will provide better stability all day.

Though ankle boots are a statement but avoid some fashion whoopsies. Firstly, avoid chunky, lug soles and bold colors – they can ruin for professional look. Also, choose matte leather over glossy ones. The same goes for fancy buckles, studs, and other attachments on the boots.
9 to 5 Office-ready outfits
- Suits with ankle boots? Why not! Try a grey or black suit with leather ankle boots.
- For a professional boss lady vibe, try wearing a grey plaid skirt with a black crew-neck. For an extra layer, try wearing the same colored blazer.
- Let's just style up for a casual day at work. Grab black dress pants with a light blue formal shirt and a beige trench coat. These all will look pretty cool together.
Weekend Vibe – Relaxed and Playful
Weekend has its own vibe – lazy mornings, unexpected plans, friends meetups. You need something that must be equally comfy and stylish, and the ankle boots fit all the boxes. These booties can suit all situations and give a perfect, gorgeous look.

If there’s one pair that can always have your back, no matter where you go, it would be none other than brown suede ankle boots. The earthy and warm color adds softness to any ensemble without being too loud. This hue perfectly matches neutral, pastels, creams, rosy, and charcoal outfits.

When styling with brown, keep the overall palette warm. Avoid bright and neon colors, they will look awkward together. Also, there should be a visible break between boots and your outfit to create an elongated effect. Additionally, layering with boots can be fun. You can choose long coats and cardigans to add more value to overall look.
Relaxed Weekend outfits Inspo
- Shopaholic? When going out, try denim with a navy plaid shirt. Add brown ankle boots and accessorize with a brown crossbody bag and sunglasses.
- For brunch with bae – a grey wool midi dress looks absolutely adorable. Want a layer on colder days? Simply throw on a grey blazer and you are all set.
- For movie night, a sweater dress looks great when styled with a blue cardigan. Wear black tights to keep yourself warm.
Final Words
Ankle boots and winter go side by side. No matter what the occasion is, these booties always have your back. Also, not to forget about the comfort, it's truly remarkable. So, this season, add these stunning pieces to your wardrobe. You will be surprised that you wont resist yourself reaching these gems again and again.
![[Stella] Square Toe Platform Chunky Ankle Boots - BLACK - 1](https://static.dreampairs.com/static/dreampairs/img/category/goods_df.jpg)