How to Make Classic Style Look Fresh and Modern

If you’re wondering how to wear classic style without looking frumpy, you’re not alone. Many women love the clean, timeless appeal of classic pieces like trench coats, blazers, and pencil skirts—but they can sometimes feel dull or outdated if not styled intentionally. And if you’re petite or fall in between standard sizing, you know how tough it is to make classic clothing work for you, not against you.

Here’s how to embrace classic style without looking frumpy—so you look polished, modern, and completely put-together.

Classic Style Without Looking Frumpy Starts with Fit

Frumpiness often comes down to one thing: poor fit. And let’s be honest—most off-the-rack clothing doesn’t fit real bodies. If you’re “too tall for petites, too short for regulars,” tailoring is your best friend. If you have a more defined waist, buy for your hips and have the waist taken in. If you’re got an undefined waist, buy for your waist and have the thighs taken in so that your pants and skirts don’t look saggy on you.

Alter those ankle pants to the perfect full length. Shorten that blazer sleeve. A $20 hem can transform a garment from sloppy to stunning.

Remember, even a plain tee looks chic when it fits beautifully. Baggy and saggy? That’s where frump begins.

Define Classic: Fashion Style vs. Personality Style

There’s a difference between loving classic fashion pieces (timeless cuts and minimalist designs) and identifying as a Classic personality dressing style (structured, polished, neutral-loving). If you’re drawn to simple garments but feel underwhelmed, you might need to blend in elements of Feminine, Creative, or Dramatic styles to create a style that feels like you.

Not sure what your mix is? Discover the your core style with my personality style quiz and find out which of the 7 personality dressing styles you have to have in every outfit to create an aesthetic that’s authentically yours.

Use Colour to Freshen Up Classic Outfits

Wearing your best colours is one of the simplest ways to avoid frumpiness. If you look luminous in soft pinks, lavenders, or pale blues, don’t avoid them just because they seem “sweet.”

Instead:

Look for pastels in structured, high-quality fabrics and cuts
If a bold colour like red, orange or hot pink are your best skin enhancer, then choose classic style garments like blazers and blouses in your best colours for a modern but still classic look
Choose updated silhouettes (a modern pink blazer or lavender blouse with detail)
Combine soft shades with deeper colours for contrast

Neutrals like black and beige might feel “safe,” but if they wash you out, they’re doing your style no favours.

Add Colour and Texture for Modern Movement

To make classic style without looking frumpy work, your outfit needs visual interest. Here’s how:

Mix fabrics like satin with tweed, denim and faux fur
Add metallics or textured accessories
Layer jewellery, belts, or scarves to add personality

Pastels can shine when paired with the right balance of texture and contrast. Don’t be afraid to let your accessories add the edge.

Look for Interesting Construction

A classic white collared shirt may be considered a wardrobe staple, but if it’s just too boring for you (and you just never wear it), if you like to add some drama or creativity to your wardrobe, why not look for a white shirt that’s constructed in an interesting way.

I was immediately drawn to this white shirt (I like to have a few in my wardrobe for doing personal colour analysis so I’m not distracting my client by wearing colours that may clash with what I’m draping them with that they can see in the mirror), because of it’s interestingly constructed sleeves and ties at the wrist. For me, it takes a boring classic white shirt and turns it into something that speaks of my personality.

Work With Your Colour and Value Contrast

If your best colours are soft and cool, chances are you have low to medium value contrast and high colour contrast. Use this knowledge to harmonise your outfits with your natural colouring.

Colour harmony is key to keeping classics fresh. The 7 Steps to Style program can guide you through discovering what truly flatters you—so your classics never fall flat.

Don’t Just Shop by Colour—Shop by Style

A frumpy look often happens when we buy something just because it’s in our palette. Don’t fall for that trap! Choose pieces that:

Suit your personality style
Work with your body shape and proportions
Have modern details or tailored finishes

The best classic pieces are the ones that do all three.

Classic Doesn’t Mean Boring—It Means Curated

Classic style is chic, versatile, and polished—but only when it reflects you. The key to making it modern? Infuse it with personality, update the fit, and style it with care.

Want hands-on help? Join the Evolve Your Style Challenge to get daily outfit prompts that will reignite your style and teach you how to remix your wardrobe with confidence.