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    Dressing Like Old Money: A Timeless Style Guide
    05.28.2024 | gifennse | Men Shoes

    Building an old money wardrobe is about investing in high-quality, classic pieces that can be mixed and matched to create a polished and refined look. This guide will provide the rules and essential items you need to dress like old money.

    Table of Contents

    Quality Over Quantity

    When building an old money wardrobe, the quality of the items you add to your collection matters. It's not about being rich or spending a lot of money; it's about recognizing and choosing high-quality pieces that exude timeless elegance and sophistication.

    Spotting Quality

    Whether you're investing in new items or hunting for treasures in thrift stores or family members' closets, the ability to identify quality is essential. Look for classic, timeless pieces that are well-made and can stand the test of time.

    Interchangeable Classics

    • Choose versatile, classic items that can be mixed and matched with ease.
    • Opt for boring classics over cheap, trendy pieces for greater versatility and longevity.
    • Quality items may come at a higher initial cost, but they offer more mileage and value in the long run.

    Timeless Elegance Over Trends

    Whimsical winds of fashion draw us in with the allure of trends, but the key to true style lies in timeless elegance. While it may seem tempting to follow the latest fads, opting for classic, enduring pieces is a smarter choice in the long run.

    Longevity of Timeless Pieces

    Choosing items that have stood the test of time ensures that your wardrobe remains relevant and stylish for years to come. Trends come and go, but timeless pieces remain a constant symbol of sophistication and refinement.

    Value and Versatility

    • Investing in timeless pieces provides exceptional value as they can be worn repeatedly without losing their appeal.
    • Opting for timeless elegance over trends allows for a more versatile and enduring wardrobe.
    • By prioritizing timeless elegance, you can make a sound investment in your personal style and financial well-being.

    Focus on the Fit

    When it comes to dressing like old money, gentlemen, the key to a polished and refined look lies in the fit of your clothing. You could invest a significant sum in a suit, but if it doesn't fit you well, it won't exude the desired elegance.

    Stick with a Conservative Color Palette

    Seriously, over 90 percent of an old money wardrobe is going to be in the colors of charcoal, black, navy, gray, white, light blue, and camel. What do all these colors have in common? They're timeless, versatile, and sophisticated.

    Maintain Your Clothing & Accessories

    Taking care of your clothing and accessories is an essential aspect of building an old money wardrobe. It's about preserving the longevity and quality of your investments to ensure they exude sophistication and refinement.

    Shoe Care

    • Own a shoe shine box and regularly condition and shine your shoes.
    • Change out the laces after 100 or 200 wears to maintain their appearance.
    • Repair scuffs and nicks promptly to keep your shoes looking impeccable.

    Clothing Maintenance

    • Replace frayed buttons on shirts and jackets to uphold their pristine condition.
    • Send automatic watches for servicing when needed to ensure their longevity.
    • Take care of clothing to extend their lifespan, unlike disposable fashion items.

    Accessorize Wisely

    When it comes to accessorizing in old money style, simplicity and timelessness are key. Avoid flashy and trendy pieces, and instead opt for classic and elegant accessories that exude sophistication without being ostentatious.

    Subtle Statements

    Choose a classic briefcase or a timeless-looking backpack to complement your outfit without overpowering it. Keep your watch and jewelry simple and understated, avoiding anything overly extravagant or gaudy.

    Signature Piece

    While it's essential to keep accessories simple, you can introduce a signature piece to add a touch of individuality without deviating from the timeless and elegant aesthetic. Remember, old money style is about confidence and self-assuredness, not flashy displays of wealth.

    Confidence is Key

    Confidence in clothing comes from practicing wearing it and knowing that it looks and feels good. When you receive compliments and feel comfortable and stylish in your outfit, it becomes your go-to ensemble, making you feel like a million bucks.

    Repetition Builds Confidence

    Just like going to the gym, practicing wearing classic, old money style clothing builds familiarity and confidence. As you become more accustomed to it, you develop a routine and feel more at ease, ultimately enhancing your confidence in your attire.

    Dress to Impress, Signal Success

    Your clothing sends a message to others without you having to say a word. Old money style allows you to portray trustworthiness, reliability, and professionalism, making it an essential element in exuding confidence and success in your personal and professional endeavors.

    Suits

    When it comes to building an old money wardrobe, the suit is a fundamental piece that exudes timeless elegance and sophistication. However, not all suits are created equal, and investing in high-quality, well-constructed suits is essential to achieving the desired old money style.

    Quality Matters

    Opt for suits that are well-made with attention to detail, such as structured chest pieces and shoulders that provide a comfortable and relaxed fit. Suits in the $500 plus range from reputable menswear stores are a worthwhile investment for a timeless and comfortable old money style.

    Comfort and Structure

    • Look for suits that offer a balance between structure and comfort, allowing for ease of movement while maintaining a polished appearance.
    • Consider trying on different styles, including those with unstructured shoulders, to find the most comfortable and flattering fit for your body type.
    • Choose classic colors such as charcoal, navy, and medium gray for versatility, with the option to introduce subtle patterns for added flair.

    Longevity and Care

    By adhering to a neutral color palette and selecting classic designs, a well-maintained suit can remain a timeless wardrobe staple for up to 20 years. When evaluating materials, opt for a super 120 or higher in worsted wool for a durable yet refined look that exudes old money sophistication.

    Dress Shirts

    When it comes to building an old money wardrobe, the dress shirt is an essential component that complements your suits and exudes timeless elegance and sophistication. Let's break down the key considerations for selecting and styling dress shirts to achieve the desired old money style.

    Classic Colors

    Opt for classic white dress shirts as they effortlessly complement any suit color, providing a versatile and timeless option for various occasions. Light blue dress shirts are another excellent choice, offering a sophisticated and versatile alternative to white.

    Versatile Styles

    • Consider classic button-down collar shirts for a more casual yet refined look that pairs well with blazers and sports jackets.
    • Explore shirts with subtle stripe patterns, such as thin blue stripes on a white background, to add a touch of classic flair to your ensemble.
    • While pastel colors like pink, lavender, and mint green can be appealing, prioritize the versatility of white and light blue shirts for a timeless wardrobe.

    Color Considerations

    Dark-colored dress shirts are generally not recommended for achieving an old money style, as the traditional approach favors lighter colors to maintain a classic and sophisticated appearance. Lighter shirt colors paired with darker jackets convey a refined understanding of timeless style.

    Collar Choices

    When selecting dress shirt collars, opt for spread collars or button-down collars for a versatile and complete look, especially when not wearing a necktie. The button-down collar, originating from Polo Fields and popularized by Brooks Brothers, offers a classic and casual aesthetic that complements the old money style.

    Material and Weave

    Consider classic Oxford shirts made from a looser, heavier weave fabric, ideal for spring and fall seasons. The durable and timeless Oxford fabric exudes sophistication and pairs seamlessly with tailored jackets and blazers, contributing to a refined old money wardrobe.

    Blazers & Sports Jackets

    Blazers and sports jackets are essential components of an old money wardrobe, offering versatility and timeless sophistication. While blazers have fallen out of fashion for many, they remain a staple in old money style due to their classic appeal and diverse material options.

    Material Variety

    • Explore options such as serge, jersey, and lightweight, breathable materials for a refined yet comfortable blazer.
    • Opt for navy or dark blue as the predominant color, as they exude a classic and sophisticated aura, making them ideal for various occasions.
    • Avoid Regatta Blazers, as they do not align with the traditional old money wardrobe aesthetic.

    Versatile Pairing

    Pair your navy blazer with a variety of trousers and colors, offering a stylish and adaptable combination that complements a range of ensembles. This versatility allows for effortless mixing and matching, enhancing the overall appeal of your wardrobe.

    Distinguishing Features

    Blazers often feature unique button designs with a nautical theme, incorporating elements such as gold or silver buttons. These distinct details contribute to the timeless charm of blazers, elevating their elegance and refinement.

    Shoes

    When building a versatile and sophisticated wardrobe, it's essential to pay attention to your footwear. Each pair of shoes should complement your suits and exude timeless elegance and refinement, enhancing the overall appeal of your ensemble.

    Oxfords: Balmoral Oxfords

    Oxfords, particularly Balmoral oxfords, are a timeless choice that exudes classic sophistication. The closed lacing system of Balmorals, exemplified by the quarter going under the vamp, makes them a perfect match for formal business attire, such as dark-colored suits and white shirts with a colored necktie.

    Brogues: Full Brogues

    The intricate design of brogues, characterized by decorative perforations, adds a touch of character to your footwear. Full brogues, also known as wingtip brogues, feature a closed lacing system and distinctive medallion, making them a versatile choice for both casual and semi-formal ensembles.

    Bluchers

    Bluchers, with their open lacing system, offer a more casual alternative to oxfords. Their versatile nature and availability in lighter colors make them an ideal choice for pairing with light-colored suits and casual attire, offering a perfect blend of comfort and style.

    Loafers

    Loafers, available in a wide variety of styles, are a must-have in every man's wardrobe. With options ranging from rubber soles for casual comfort to leather soles for a more refined look, loafers can be paired with a range of outfits, from casual suits to relaxed summer attire.

    Polo Shirts

    When it comes to building an old money wardrobe, the polo shirt plays a pivotal role in achieving a versatile and sophisticated ensemble. Unlike inexpensive options, investing in higher-end polos elevates your style and offers a multitude of outfit possibilities.

    Versatile Pairing

    The beauty of a polo shirt lies in its ability to complement a range of trousers, making it a versatile addition to your wardrobe. Dress down a suit by pairing it with a polo for a refined yet relaxed look, or elevate a casual pair of trousers or shorts by incorporating a high-quality polo.

    Color Palette

    • Opt for classic neutral colors such as white and dark navy, aligning with the traditional old money aesthetic.
    • Explore brighter colors that add a touch of vibrancy to your wardrobe while still maintaining a sophisticated allure.
    • Avoid overly bright and flashy patterns, as they may not blend seamlessly with the interchangeable nature of an old money wardrobe.

    Neck Ties

    Despite reports of the necktie's demise, it remains a timeless and essential accessory in men's fashion. The use of neckwear has deep historical roots, dating back thousands of years, and continues to be a symbol of sophistication and style.

    Classic Color Palette

    When selecting neckties for an old money wardrobe, opt for classic colors and patterns that exude timeless elegance. Regimental stripes in muted tones are a traditional choice, while solid navy and woolen neckties offer a refined and sophisticated aesthetic.

    Subtle Patterns

    • Introduce subtle patterns like small paisleys for a touch of classic flair without overwhelming the ensemble.
    • Exercise caution with dots, ensuring they are not overly bold or conspicuous to maintain a refined look.

    Khakis

    When it comes to incorporating chinos, also known as khakis, into your old money wardrobe, the key lies in achieving the proper fit for a polished and refined look. With a wide variety of colors available, it's advisable to stick with neutral palettes. However, if you're looking to add a unique touch, consider options like Calvary twill, moleskin, and 11-wale corduroy for a classic and sophisticated appearance.