5 Designer Boots Worth the Investment

the-alyst.com stuart weitzman highland

As soon as the weather outside begins to hint of cooler temperatures, I start researching boots for the upcoming season. While I’m a lifelong New Englander, I can’t say that I am actually a fan of cold weather; however, I do love being able to wear a great pair of fashion-forward boots on a chilly day! I guess that’s the style trade-off for living in the tundra of Boston during the winter months.

For the last five or more years, I’ve made the decision to purchase one new pair of designer boots each fall/winter. Adding these to your wardrobe is definitely an investment, but a well-made pair of boots will last you for many years, and if you opt for a classic style, they’ll never look like they’re from ‘last season.’

This year, I decided to step outside my comfort zone and purchase a pair of light gray, suede, over-the-knee boots by Stuart Weitzman. When it comes to boots, I typically play it safe and wear classic hues like black or brown, but every time I passed these beauties in the store, I couldn’t help myself from stopping to admire them. While they are probably not my most practical winter boot, they are definitely my most fun and eye-catching!

If you’re in the market for new boots, I’ve rounded up a few of my top designer picks. A fair warning — I can’t promise that these boots will keep your feet super warm or dry, but I can guarantee that you’ll make a statement. Happy boot shopping!

the-alyst.com, stuart weitzman highland

the-alyst.com, stuart weitzman highland
the-alyst.com, stuart weitzman highland

The A-Lyst for Designer Boots Worth the Investment

the-alyst.com, stuart weitzman highlandStuart Weitzman Highland Over-the-Knee Boots

These 4-inch suede boots were not made for walking, but my goodness, I still love wearing them! The Highland boot comes in a number of great colors, including topo, which is the light gray/taupe hue that I purchased. The suede finish paired with the over-the-knee style gives an instant fashion boost to whatever you’re wearing and I’ve found them to be surprisingly versatile. I love pairing mine with skinny jeans, black leggings, and skirts. If a higher heel isn’t for you, I highly recommend the Stuart Weitzman’s Lowland or the Stuart Weitzman 5050 boot.I own the 5050 in black leather from a previous season, and they are by far my most comfortable boot!

Valentino Rockstud Ankle Bootie

This ankle bootie offers a classic silhouette with a fun pop of detail! If you shy away from boots with a heel, but still want something with a bit of interest, this Valentino pair would be a great investment. This boot can be dressed up or dressed down (I personally love how it looks with a big, chunky knit sweater and leggings), and if you’re a fan of Valentino’s Rockstud line, but aren’t quite ready to sport the flashier Rockstud Leather Slingbacks, this is an excellent, more understated option. Not to mention, I rate them an A for comfort!

Chanel High Boots with Open Lacing

I think this boot is SO cool! I just adore the open area and exposed lacing/stitching. These boots definitely catch the eye with their unique detail and use of texture, and to me, the tweed version brings back the look of classic Chanel, while keeping them young and fun by adding a modern, unexpected twist. This boot comes in both a short and high style, and both are equally as striking.

Jimmy Choo Youth Leather Biker Boot

Jimmy Choo has kept the style of this boot fairly consistent over the last few years, and I’m not surprised, as this is a great moto boot! I love how the shiny buckles contrast the look and feel of the textured black leather; it’s the perfect mix of chic meets grunge. As stylish as this boot is, it’s also very comfortable. The heel is low enough to allow for pain-free walking across the city, so I wouldn’t be shocked if you start repeatedly grabbing this boot for your weekend excursions. If you prefer a warmer boot, Jimmy Choo also has a rabbit fur-lined biker boot that is oh-so-soft and cozy. Either option is a total win-win!

Christian Louboutin Adox Leather Bootie

Every woman needs a classically chic high-heeled black bootie in her shoe collection, and if you’ve been on the hunt for the perfect pair, this could be it! Beyond showing off Louboutin’s signature red sole, this ankle boot is the answer to dressing up your skinny jeans and that cute shift in your closet that you never seem to wear. The reason I love this bootie so much is because both the heel height and height of the boot on your ankle are just right for everyday use. If you’re new to the world of Louboutin’s and are worried about scuffing up that pretty red sole after one use (…which you ultimately will…), there are a few cobblers in the Boston area (Waban Shoe Repair is my go-to) that can help to protect and/or restore them.

Outfit Details:

Top: Halogen Crewneck Lightweight Sweater in Ivory Cloud

Shawl: Gucci Pattern Shawl with Fox Fur Trim in Light Gray 

Pants: DL 1961 Jeans – Emma Power-Legging in Flatiron

Shoes: Stuart Weitzman Highland in Topo Suede

Bag: Chanel Large Classic Flap in Black Caviar Leather with Silver Hardware (similar here)

Sunglasses: J.Crew Factory Sunglasses (no longer available, similar here)

Lipstick: Chanel Rouge Allure Gloss in Seduction

Photos by @KateSW