A well-crafted pair of booties that fit your personal style has the power to transform any outfit you wear from good to great. Spending a bit more on a classic pair that will never go out of style makes good fashion sense. While I will save on trendy seasonal items, I am willing to buy a higher priced well-made pair of boots that will add polish to my outfits and will last me several seasons.

There are a few key pairs you should consider having in you wardrobe. A flat everyday Chelsea or pointed toe boot, a water-resistant bootie, a dressier block or kitten heel, and some type of lug sole, combat or lace-up hiker are the four I strongly recommend. I suggest you own at least one pair of taupe or tan-colored boots which literally will go with anything. Read on for my Top 10 pairs of booties that will always be in style and will instantly elevate all your fall and winter outfits.

Rag & Bone makes beautiful boots and I own and love several pairs. A chunky 2″ stacked heel and covered elastic goring provide polished updates to this almond-toe Chelsea boot that serves as a wardrobe-spanning closet staple. Timeless. In 3 colors and highly reviewed. Order half size up for best fit.

Rover Chelsea Boot $395

With an edgy cutout heel and metal detailing, these fashionable yet timeless booties from Alexander Wang will be in your closet for years.

Kori Block Heel Bootie $595

These are my “go-to” everyday bootie and I own them in several colors including this neutral taupe that matches everything. In seven colors and part of Bloomingdales “Buy More Save More” sale through 10/24. Rarely on sale but selling fast.

Yale Chelsea Bootie $179

This block-heel bootie from Aquatalia has a signature waterproof finish to help keep you looking your best no matter the forecast. Also in black and navy. A classic silhouette.

Fuoco Waterproof Bootie $395

With a 2.4″ heel, these dressy pointed toe booties from Marc Fisher will elongate your leg and elevate almost any outfit. In five colors, and part of Bloomingdales “Buy More Save More” sale through 10/24.

Jarli High Heel Bootie $189

With a 2.3″ heel on a comfy lug sole, these booties from Paul Green are a bit edgy but not over the top. Love the gunmetal buckle. Part of Bloomingdales “Buy More Save More” sale through 10/24.

Dynamic Buckle Boot $485

Crafted from buttery leather, this updated Chelsea boot from Madewell has a pared down look thanks to the sleek covered insets. The Cloudlift Lite padding feels extra comfy. I own these in both brown and black. Up to 30% off right now.

Ainsley Chelsea Boot $198

This water-repellent lug sole bootie from Vince will always look fabulous. In five colors, but many sizes selling out fast.

Vince Lace Up Bootie $395

Sleek, uninterrupted lines upgrade the look of this patent leather Aquatalia water-resistant bootie made in Italy for comfort and style, whatever the weather. Chic and cool. Limited sizes available.

Ulyssa Water Resistant Bootie $495

Hit the pavement in these Madewell hiker-inspired lace-up boots with utilitarian lug soles. Made of rich leather with padding around the ankle, they’ll lend an outdoorsy look to all your looks. Also in black. Up to 30% off right now.

Citywalk Lugsole Hiker Boot $198

The Style Power of a Perfect Pair of Classic Booties was last modified: by

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