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Style Your Rockport Boots For The Season: Ladies Edition

2025-04-29

The chilly season is here, and as we pull our coats and scarves out of storage, it’s also time to focus on the perfect pair of boots.

We believe every woman deserves stylish, comfortable footwear for the winter season—which is why we’re thrilled to introduce three brand-new ladies’ boot styles!

Read on to discover the latest trends and get expert styling tips to elevate your look this season.

Fashion For The Season

As we all know, a colder climate brings the fun of layering our outfits! It's also a great opportunity to play around with your style and experiment with different fashion aesthetics.

And of course, who doesn’t love a statement boot moment? For our fashionistas out there who love to strut in style while staying warm, we know you’ll love what we have in store for you this season!

Styling Our Rockport Ladies Boots

Isalina

Our Isalina boots feature a grunge-style lug sole, which is not only fashionable but also perfect for all-day comfort! When we say boots made for walking, we certainly mean it!

This sleek black boot will match just about any style, which is yet another reason why it would be perfect for your cold-season wardrobe. To paint a clearer picture, here are some fresh, funky ways to style these boots:

The Business Grunge Look

This fashion aesthetic is the perfect combination of edgy and business. It exudes that ‘girlboss’ energy and is perfect for the winter season palette.

To achieve this look, begin with a pair of dark check trousers. Pair them with a high-neck black bodysuit and a black blazer. Add some accessories, such as a belt with a unique buckle and bold earrings to balance the high neckline. Complete the look with your Isalina boots, and you're good to go!

Business Grunge

Utility Chic

Utility chic is all about combining the workwear look with a contemporary flair. Think big pockets, buckles, and overalls.

To create a utility-chic look, grab your favourite pair of cargo pants, preferably a cuffed pair. Next, pair them with a black polo t-shirt and throw on a cropped shacket to match. If it's really chilly, an infinity scarf would look great! Finally, throw on your Isalina boots. Pro tip: if your cargo pants aren’t cuffed, try tucking them in to give your boots their shining moment.

Dark Feminine

The dark feminine look is truly an iconic ‘it girl’ fashion aesthetic. There’s something so alluring yet powerful about this look, and in colder seasons, when you can add layers, it’s even better!

Begin with a dark silk slip dress. Add a skin-tight polo neck t-shirt underneath. Pair with black stockings, and if your dress is on the plain side, opt for patterned black stockings. Next, this look definitely calls for bold siren makeup, with a lovely, deep maroon lipstick. Finally, add some ankle socks with frilly details so they peek out of the top of your Isalina boots.

Other Dark Fem

Chole

Our Chole boot features an almond-shaped toe and a stylish buckle around the ankle. Available in two colours—natural brown and black—this boot is perfect for a number of looks and offers a softer winter vibe.

Retro Girly
There’s just something about ankle boots that fits perfectly with a retro look.

Nothing says retro quite like corduroy. For this look, grab your corduroy pinafores and layer them with a long-sleeve top underneath. Have fun with the top—whether balloon sleeves or bell sleeves, opt for something unique. Next, wear some stockings and throw on your Chole boots.

But wait, you’re not done! Accessories are everything when it comes to a retro look, so find your slouchy beanie and add it to the outfit, alongside a pair of cat-eye sunglasses.

Pinafore

Cottage Core

The cottage core look is a soft, earthy, and feminine aesthetic. The palette consists of natural tones and flowy layers.

Begin with a long A-line skirt, paired with a balloon-sleeve blouse and a matching corset-cut waistcoat. If it’s an exceptionally cold day, you can wear tights underneath your skirt. Accessorise with long necklaces or other natural jewelry. Finally, slip on your Chole boots, and your look is complete!

How Will You Be Styling Your Boots This Season?

 There you have it: two boots, styled five different ways!

Of course, the options are endless—after all, you can never go wrong with a good pair of boots. Now that you’ve got some style inspiration for the season, how will you be styling your Rockport boots?

Be sure to tag us on social media so we can see how well you rock your Rockports this season!