Have you ever wondered how to dress classic while staying true to yourself? Last December, when I ran my visual style identity workshop, one of my friends, who I’m going to call Susan for this episode, not her real name, came to it to support me, and during the introductions she shared something with the group that made me want to take a fresh look at classic style. She said she hoped to learn about building a wardrobe based on classic pieces but most importantly, she wanted her style to express who God made her to be.
This is an important truth. Classic style isn’t just about following predetermined rules. When people ask how to dress classic, they’re often given a standard list of wardrobe essentials – but classic style looks different for every personality type and body design. Your unique version of classic aligns with who you truly are.
Historical Origins of Classic Style
Classic style emerged in the early-to-mid 20th century, shaped by designers like Claire McCardell and Coco Chanel. They created investment pieces for post-WWII American prosperity: neutral colors, simple silhouettes, quality materials.These designs reflected East Coast and European upper-class aesthetics, coinciding with the rise of ready-to-wear clothing. Pretty soon everyone was wondering how to dress classic.
By the 1980s, this evolved into the “dress for success” movement. But today’s world is different. We’ve moved beyond one-size-fits-all solutions.
Take the “little black dress” – it’s on every classic wardrobe list. But what if black isn’t your best color? What if the traditional sheath silhouette doesn’t complement your body design? Modern classic style needs personalization.
FIRM Fixations and How to Dress Classic
Many people approach classic style from fear rather than choice. The FIRM fixations are a model developed by Personality Hacker, based on Myers-Briggs types and explain these reactions:
- Freedom-focused people (usually EPs) feel trapped by rigid rules, including when it comes to style
- Some (usually IJs) seek Invulnerability. This could be through “safe” clothing choices
- Others (usually IPs) chase Rightness, and don’t think they should have to obey strict lists
- Management-oriented people (usually EJs) try to control their image through traditional pieces in order to look like they should be in charge. Someone with a management fixation likely originated the Dress for Success guidelines, creating rules that just happened to work with their own body design.
But authentic style comes from understanding your design, not from following rules. When you know what works for your body, you can confidently move between from one trend that works to the next, skipping those that don’t serve you.
Adapting Classics to Your Body Type
Let’s look at how classic style adapts to different body designs. The traditional pencil skirt and A-line skirt are both considered classic, yet they work best for different bodies:
- Hourglass shapes need A-line or fuller skirts
- Figure-eight and oval shapes are great in pegged styles – pencil skirts with slightly tapered side seams
- Rectangle shapes look balanced in straight skirts
- For Triangle and inverted triangle shapes it depends on individual hip shape
This principle extends beyond skirts. Take the classic sheath dress:
- An hourglass might need a fit-and-flare version or a wrap dress
- A rectangle could wear the traditional straight cut
- An oval needs strategic seaming for balance
How to Dress Classic Beyond Black
Let’s reimagine the “little black dress”, a simple dress to wear to a range of events from business meetings to elegant evenings out.
- Navy is a very classic option which often looks better on people than black
- Emerald green is a lovely option for alot of people with either green or brown eyes
- Burgundy is both current and classic. If you look good in burgundy lipstick, why not a simple day-to-night burgundy dress?
- Deep purple is an unexpected option.
The key is identifying pieces that:
- Work with your body design
- Come in colors that enhance your complexion
- Match your lifestyle needs
- Feel authentic to your personality
Action Steps
- This week, try on different skirt shapes. Notice which feel most natural.
- To begin identifying what style lines and themes will be classic for you, get started on your Signature Style journey with your Essential Signature Style Guide.
- Join me next week when we’ll dive deeper into building your personal classics collection.