Your 5-Step Guide to Preppy Style

Your 5-Step Guide to Preppy Style

Classic, crisp, clean. These are the pillars on which all preppy outfits are built. No matter the destination, the aim is to look sharp and effortlessly put together - which is not always an easy feat.

But worry not. We have created a five-step guide to preppy style that will help you hit the mark, every time. 

Step 1: Know Your Preppy Style Staples

The fabrics, prints and textures of preppy style are timeless and sophisticated. We’re talkin’ cotton, wool and cashmere; gingham, seersucker and madras; tweed, corduroy and cable knitIt’s familiar, it’s comfortable and incredibly versatile. Pair any of these with chinos and loafers and you’re ready to make an entrance. 

Preppy Outfit details

To look put together and not thrown together, make sure these evergreen closet staples not only fit appropriately, but are also cut or tailored for current-day wear. Some shapes will never go out of style, while others shift over time. Body type and personal style will dictate what silhouette is best for you. Follow your gut - or give us a call and we’ll gladly offer advice. 

As a general rule, if you feel like you’re staring back at your middle-school self, make sure it’s due to nostalgia - and not your actual teenage wardrobe! 

Step 2: Coordinate Your Colors

At the foundation of the preppy gentleman’s year-round style are bright whites and handsome blues - mainly sky tones and navy. Color and pattern are easily layered over this all-purpose palette. 

Cool-weather looks tend to be on the conservative side, featuring masculine and mature tones that include burgundy, terracotta, emerald, mustard and mocha.

 Preppy Style Color Palette

Patterns prominent at this time of year are collegiate stripes, argyle, herringbone and tartan. Ensembles feel warm, approachable and refined. 

Spring and Summer usher in more youthful and lively colors. Pastel as well as vibrant blues, greens, pinks and yellows are popular, as are playful patterns like florals, polka dots, gingham and paisleys. Warm-weather preppy looks tend to be polished, yet casual and fun.  

Step 3: When In Rome (or Want To Be)

Preppy looks draw inspiration from a variety of gentlemanly sporting events and social circles.

Grounded in tradition, themes are often centered around Ivy League pastimes like polo and horse racing, cricket and rugby, rowing and sailing. Locale also serves as an influence, such as the English countryside, the Hamptons, Martha’s Vineyard, or the South of France. 

Example of Cool Weather Preppy Style

With so many colors, patterns, textures and themes to choose from, it can be easy to go a bit overboard. For maximal charm and sophistication - be it dressy or casual - build your ensemble around a single theme. Opt for a central focal point, i.e. color or pattern on top with neutral on bottom, or vice versa.  

Step 4: Follow the Preppy Style Trends

Prep has been a mainstay in menswear since the early 1900s - which means it’s been subject to numerous trends and shifts over the decades. What once was considered elegant or cool might be dated today. 

For instance, popping your collar used to be the ultimate finishing touch, but these days it’s a pretty major fashion faux-pas. As another example, it was customary to tie your sweater around your shoulders or waist years ago, but that’s a no-no for the modern preppy gentleman.

Some current trends you might consider trying include:

  • Rolling and cuffing your pants and wearing no (or no-show) socks with boat shoes, loafers or oxfords. Jeans, chinos and khakis are all safe styling bets, and other trousers may work as well.     

Preppy Style Trends

  • Donning a pair of GTH (Go To Hell) or critter pants. These loud and proud trousers have been getting the party started since the 50s, but have been stepped up a few notches in recent years. 


Step 5: Polish with Preppy Accessories 

As is always the case, the thoughtful incorporation of fine accessories adds polish to your ensemble and infuses it with your personality. 

If wearing a statement color or print, plan on one to three complementary (but not matching) or perhaps muted accessories. When keeping your look more simple, dare to play with several accessories, one or a few of which can be a bit bolder. 

Some of our favorite ways to spiff things up at R. Hanauer include: 

Preppy style necktie in Liberty London Print

  • Featuring a unique pocket square, embroidered or reversible belt, standout watch, or noteworthy eyewear.

reversible belt for preppy style guide

  • Choosing an unexpected element, like a dashing ascot, handsome suspenders, or funky socks.  


With a change of season on the horizon, we’re eager to see your favorite #RHanauer warm-weather looks as well as those you look forward to wearing when Fall sets in. For preppy style inspiration and ideas, be sure to follow us on Instagram, Facebook and YouTube!