Building an Elevated Wardrobe for Any Occasion

In today’s world of fast fashion and endless options, building a man’s wardrobe that actually works can feel overwhelming. But there’s something timeless — and empowering — about having a selection of well-made, versatile pieces that you can count on, no matter the occasion. Whether you're building your wardrobe from scratch or refreshing it after a lifestyle shift, starting with a solid foundation is the key. 

Charlie Rossi's Design Philosophy

At Rossi Clothiers, we believe in clothing that’s not driven by trends, but by timeless style, comfort, and confidence. Rossi has spent decades helping men dress appropriately for success and comfort with elegant, and timeless style. Rossi’s philosophy for timeless style means staying away from trends. He believes in “quality over quantity, form with function, and dressing with a firm but subtle confidence."

What is a Foundational Wardrobe?

Building a foundational, or a working wardrobe, isn’t about owning dozens of pieces,” says Rossi. “But it's also about owning the right ones .” 

“You’re going to want garments that serve you in multiple ways,” he explains. “For instance, in the beginning you’ll want to select garments that are versatile, that fit well, and that reflect a person’s personality without screaming for attention. Look for pieces that work for a business appointment, or can go to a casual event at a moment’s notice.

Shown here: Castangia Sport Coat - Hand made in Sardinia, Italy, Emanuel Berg Shirt, Seaward & Stearn horse tie, Simonnot Godard horseshoe belt, Robert Jensen pocket square, Samuelsohn trousers.

Shown here: Left Coast Tee linen jacket, Jerry Kaye striped fine gauge short sleeve sweater, Robert Jensen pocket square, Hiltl trousers.

You also have to be tuned in to how to be appropriate for the event or appointment you’re going to. You have to know the people you are dealing with.  For instance, if you are in sales, and are calling on a member of the farming community, you’re going to want to look professional, but appropriate. I recommend a sport coat, no tie and jeans in this instance. You want to make people feel comfortable, and approachable. 

This philosophy isn’t about being flashy or chasing trends. As Charlie often says, “You can be quietly noticed, or you can stand out like a sore thumb.” The goal is always the former: a refined, effortless look that suits you and your lifestyle.

Where does his design philosophy come from? Rossi suggests, “Look at movies and tv over the years. You’ll notice what has staying power. 

The Power of Versatility

A good wardrobe adapts. Whether you’re heading to a meeting, a dinner party, or a casual brunch, you shouldn’t have to reinvent your outfit. By focusing on quality materials, timeless designs, and neutral tones, your core pieces can flex across seasons and situations. The key is knowing how to layer, pair, and present them with subtle confidence. 

1. A Classic Suit

If you only own one suit, let it be a charcoal gray. It’s the most versatile color — soft enough to work for both weddings and funerals, but neutral enough to pair easily with a range of shirts, ties, and shoes. Navy is another staple, and medium gray works beautifully for business or social events. 



Made-to-measure suits from Rossi Clothiers allow you to choose the perfect fit and fabric, offering longevity and comfort tailored to your exact lifestyle. 

Shown here: Samuelsohn Charcoal Grey Sharkskin Suit, available by special order.

Shown here: Samuelsohn Navy Blue Double Twist Blazer, available by special order.

2. A Timeless Navy Blazer

One of the most flexible pieces you can own, a navy blazer works across the entire wardrobe spectrum. Pair it with jeans and loafers for a smart-casual look, or dress it up with slacks and a tie for more formal occasions. It’s a go-to piece that always delivers polish without pretension. 

3. Well-Fitted Dress Shirts

Start with the basics: crisp white, light blue, and maybe a subtle pastel. Add a mix of collars — like a classic spread or a button-down — depending on the look you're after. Quality shirts, especially in linen or lightweight cotton, elevate any outfit, and Rossi’s custom shirts ensure the perfect balance of structure and comfort. 

Shown here: Stenstrom's dress shirts, wide variety available in store.

4. Trousers That Go the Distance

You don’t need a dozen pairs of pants — just a few great ones. Charcoal, navy, and khaki trousers offer maximum flexibility. A good pair can move from the boardroom to date night to Sunday brunch with ease. Look for high-quality wool blends or linens with subtle texture and breathability for all-season wear. 

Shown here: Alexander Julian Sport Coat, Gran Sasson linen t-shirt, Seaward & Stearn pocket square, Hiltl trousers.

5. A Thoughtfully Selected Sport Coat

Sport coats add depth and character to your wardrobe. Blends of silk, linen, and wool provide dimension and reduce wrinkling — especially important for warmer months. A well-tailored sport coat in a seasonal fabric is perfect for events like engagement parties, dinners, or casual business settings.

Elevated Casual Wear

The foundation of great casual wear lies in quality fabrics and great fit. Invest in well-made denim, chinos, and linen trousers. These pieces should feel comfortable while still presenting a polished, elevated appearance. 

Shirts & Polos That Layer Well

From breathable polos to richly detailed shirts, look for versatility. Layering is essential — particularly in transitional seasons. Natural fabrics, such as cotton and linen, offer excellent breathability and allow for effortless layering.

Shown here: Jerry Kaye dip dyed linen shirt and dark rinse jeans.

Shown here: Jerry Kaye lightweight leather jacket, Bar Kaffe graphic t-shirt, & grey rinse jeans.

Jackets & Outerwear

A tailored overcoat or leather jacket should be more than just a garment; it should be a statement piece. Look for refined details like structured shoulders, a well-crafted lining, and weather-appropriate fabrications that demonstrate exceptional craftsmanship.

The Right Footwear for the Job

Timeless Shoe Styles

A well-rounded shoe wardrobe doesn’t need to be complicated. Begin your selections with these essential picks:

• Penny loafers – A true staple; wear with jeans, trousers, or a suit. 
• Tassel loafers – Versatile and slightly more refined; great with suits or dressy casual looks. 
• Cap toe dress shoes – Perfect for business or formal wear. 
• Suede slip-ons or Venetians – Ideal for spring and summer; add texture and comfort.

Shown here: Crockett & Jones Shoes & Belts. Hand Made in England.

According to Charlie, suede is no longer just a fall fabric — “It’s year-round. Even the Duke of Windsor wore suede shoes in summer.” 

Look for details that signal quality and timelessness, like leather soles or sleek, understated silhouettes. At Rossi, you’ll also find options with subtle rubber soles for added comfort, without sacrificing appearance. 



Ties, Pocket Squares & More

Accessories are where personal style shines. “You make your statement with a tie,” Charlie says. Woven ties — with depth and texture — often come across more elegant than printed ones. Smaller motifs and tonal patterns are more refined and versatile. 



Pocket squares, belts, and watches should complement, not compete. Think of accessories as the finishing touches that quietly elevate the entire outfit. 

Shown here: Meghan Spivey hand carved Bone Bear & Bull tie bar, Seaward & Stearn tie, Stenstroms shirt, Samuelsohn sportcoat.

Tailoring As You Grow

Our bodies and tastes change — your wardrobe should evolve too. At Rossi Clothiers, on-site tailoring ensures your garments are always fitted to perfection, no matter how your life shifts. 



Seasonal Transitions

Add lighter textures in spring and summer, and lean into deeper colors and heavier wools in fall and winter. Rather than starting over, rotate and layer intentionally. 



Wardrobe Longevity

Quality garments last when properly cared for. Store pieces well, clean them as recommended, and invest in tailoring when needed. A great piece should serve you for years, not seasons. 

Start with Rossi Clothiers Today

Building a wardrobe that works isn’t about excess — it’s about intentional choices, made with your life and style in mind. At Rossi Clothiers, we’re here to guide you through that journey with expert advice, premium fabrics, and a truly personalized experience.

Attend our upcoming Samuelsohn Design event from April 10-19, offering special pricing on custom tailored menswear. Enjoy this special opportunity to meet with Samuelsohn representatives who will assist you with your wardrobe selections.