I enjoy a good video game. I’m lured in with a compelling hook, intriguing plot twists, and captivating character development. I ride shotgun as the protagonist builds alliances, overcomes obstacles, and enhances his abilities to reach new levels of mastery. My rapport with the character is deepened by empathy and heightened by an overwhelming urge to help him succeed. Against my will, I feel joy, sadness, anger, confusion, and determination as hours fly by. Eventually, we (both) emerge victorious, accomplished, and enlightened.

Developing personal style is very much the same, except you are the main character. As you progress, knowledge is gained, abilities are enhanced, and diverse allies empower your road to success. Consider me your first ally, your trusty style advisor. My role is to help you confidently and stylishly navigate this wonderful game called life. Before we begin, it’s imperative that I remind you of my style principles.

Fit Comes First  Irrespective of money spent or how trendy an item maybe be, poor fit drains your style points instantaneously. Find a good tailor, and hold on for dear life. His alliance will prove invaluable.

Keep It Classic  Wardrobe staples such as navy blazers and black cashmere V-neck sweaters pair effortlessly with other classics such as dark denim and crisp-white button-down shirts. The versatility increases the usage of each item and the endless number of outfit combinations.

Quality Over Quantity  Consumerism (the need to have more and more stuff) is multiplied by fast fashion (quantity over quality) and compounded by social media. But the truth is, you don’t need a ton of items to be stylish with the best of them. Invest in key pieces constructed from quality materials. They last long and will serve you well.

Now let’s get started. Today’s journey starts you off with two classics: a pair of dark denim jeans and a button-down shirt. Since you applied my three principles, your jeans are hemmed and tapered to perfection, and your button-down fits trimly without constriction. Your mission is to create outfits that elevate these two items without falling prey to fashion trends. I will guide you through the levels, providing tips as needed. Don’t be afraid to make it your own; that’s what style is all about. Good luck, and I will meet you stylishly on the other side!


Level 1

Texturally Speaking

texture outfit style

  • Dark denim jeans
  • White button-down shirt
  • Black cashmere cardigan
  • Suede monk strap shoes
  • Pocket square
  • Double-breasted blazer with eye-catching texture

*Style Tip: Layer with texture to add visual depth. This look combines a cotton shirt, cashmere cardigan, and tweed jacket.


Level 2

In the Trenches

trenches outfit style

  • Dark denim jeans
  • Contrast collar button-down shirt
  • Grenadine silk tie
  • Polka-dot scarf
  • Double-breasted trench coat
  • Chelsea boots

*Style Tip: Chelsea boots tell the world you own more than sneakers. Keep them polished for maximum impact.


Level 3

Effortlessly Casual

effortless outfit style

  • Dark denim jeans
  • Gingham print button-down shirt
  • Quilted vest
  • Blazer
  • Pocket square
  • Tan leather sneakers
  • Tan leather gloves

*Style Tip: Match your leather accessories to demonstrate attention to detail.