Fall and Winter Shoe Guide

The air is filled with the smells of pumpkin spice and hot cocoa. The cold seasons are upon us, which means you need to outfit yourself with the right footwear to stand up to chilly temperatures and precipitation.

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Rain Boots (galoshes, gumboots, Wellingtons)

Named after the first Duke of Wellington, the classic rain boot is a more waterproof version of the Hessian boot common in the 19th century.

Wear them: In rainy weather
What to look for:

  • Leather lining for extended durability
  • Thick insoles equal added warmth and insulation

Styling Tips

For women: Wellingtons are versatile, working with leggings, skinny jeans, a skirt, or a dress.
For men: Tuck your jeans into the boots or cuff them for a three-quarter trousers look. Top with anything from a clean shirt to a casual tee.

Snow Boots

Wear them: Hiking or exploring snowy streets
What to look for:

  • Water-resistant synthetics or water-proofed leather
  • High warmth ratings that don’t sacrifice breathability
  • Treaded rubber soles

Styling Tips

For women: As snow boots can look bulky, make sure you wear fitted clothes. Avoid straight or boot cut jeans.
For men: Keep it rugged and warm with jeans or chinos.

Work Boots

Wear them: When you’re working hard and need extra support and protection
What to look for:

  • Plenty of insulation
  • Steel toes (for construction workers)
  • Reinforced soles to prevent slips on slick surfaces

Styling Tips
For women: Much like snow boots, avoid any ill-fitting clothes, which could make you look unbalanced.
For men: Stick with jeans, wool trousers, or khaki cotton chinos.

Ankle Boots (booties, shooties)

Like your average boots but shorter.
Wear them: When you need to dress up your winter look
Styling Tips
For women: Ankle boots come in all shapes and sizes, including flat, wedge, heel, cut-out, laced, and buckled. Wear leggings, pull on some neutral-colored socks, or cuff your lean jeans to show a little ankle.
For men: Match ankle boots with jeans, dress pants, or a full suit.

Athletic Shoes (sneakers, tennis shoes, tennies, trainers)

Wear them: In the gym or out and about when you want to stay casual and comfortable.
What to look for:

  • Proper support depending on the sport or activity
  • Colors and designs that stand out but are easy to match

Styling Tips
For women: From skirts and dresses to jeans and sweaters, the sky is the limit.
For men: Match sneakers with essentially anything. Sneakers with suits are a contentious issue, but you can pull it off with a pair of basic, minimal sneakers.

Maintenance and Care


Salt stains

  • Remove salt stains with a mixture of white vinegar and water.
  • Dab the solution onto your boots with a clean cloth and wipe away with a dry towel.
  • Air dry before you buff with a soft cloth


  • Dip a soft cloth in water and then baking soda.
  • Gently rub the cloth onto the scuffed area.
  • Wipe away with a damp cloth and buff to dry.


Stains and scuffmarks

  • Sand the stain using a fine-grain emery board.
  • Use a kneadable eraser to rub away stains.
  • Use a clean terry towel or toothbrush to raise the suede’s nap.

General care

  • Don’t leave your shoes in the sun.
  • Avoid harsh chemicals.
  • Use shoe trees to maintain the shape and soak up any excess moisture.



  • Dip a damp cloth in scouring powder.
  • Rub the scuffed area.
  • Wipe with a clean cloth and buff dry.

General care

  • Keep your rubber shoes clean with warm water and liquid dishwashing soap.
  • Remove any caked-on dirt with a toothbrush.
  • Store your rubber shoes in a clean, dry area.

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