What’s My Style? Classic Style

This article on classic style is the next installment in the series on unique personal style where we are exploring fourteen different style personalities. The purpose of this series is to help you find your unique personal style.

Knowing your style can provide focus when shopping and putting together outfits. Getting dressed is a breeze once you know what message you want to convey with your clothing choices.

Stick to the classics, and you can’t ever go wrong. I see old ladies on the street who have fabulous style and realize it’s because they are probably wearing really classic items that they’ve had for years and years. I think if you find something that suits you, you should just stick to it.

Alexa Chung
three classic stye outfits with blazers

What is classic style?

If you prefer simple, elegant clothing that doesn’t change much in fashion, your style is classic. Your three style words may be polished, refined, and timeless. Sleek, sophisticated, and effortless may also be the message you want to convey. Other words that come to mind include traditional and conservative.

All of these describe classic style.

Someone who has classic style is aware of trends and may indulge in them from time to time, but most of a classic wardrobe remains stylish year after year.

You don’t fall victim to trends. You are confident enough to ignore them and still feel and look fashionable.

The woman who favors classic style is confident and doesn’t need the latest trends to look and feel good. She knows what works and sticks with it, choosing timeless pieces that last.

Some well known public figures and celebrities with classic style are Princess Diana, Kate Winslet, Audrey Hepburn, and Victoria Beckham. Notice these ladies are from different generations but their style is the same? Classic style is timeless.

The Elements of Classic Style

Clean silhouettes

 The silhouette is the overall shape a dress or garment creates when it hangs on the body. Fitted or semi-fitted  or tailored silhouettes are elements of classic style. Garments are not too tight or too loose, and flatter the figure.


Colors tend to be mostly neutrals like black, navy, cream, grey or white but you can enjoy a pop of color with neutrals and still fall under classic style. Most of the wardrobe basics and staples will be in neutral colors.


Patterns or prints for the classic wardrobe will include basics like dots, stripes, and leopard.

Other animal prints like python or snakeskin, and zebra are also classic.

Florals will be simple and not busy. Plaid is another classic print.

These prints may increase in popularity at times and become “trendy” but they will never go “out of style.”

Just because a piece is made in a classic print doesn’t mean the piece is a classic itself. Take for example a cold shoulder blouse. Those were trendy and may have been made in a dot print or leopard print but that doesn’t make the cold shoulder blouse a classic.


 Fabrics include silks, cashmere, wool, leather, and cotton. Quality is a trademark of classic style, so fabrics will be those of higher quality.

classic tan suit women's office outfit

What should I wear for classic styling?

 “One is never over-dressed or under-dressed with a Little Black Dress.”

– Karl Lagerfeld

Classic garments include button up shirts, dark wash denim, tailored/ straight leg jeans and pants, blazers, chino shorts and pants, and pencil skirts.

Dresses will follow clean lines with styles like sheath dresses, slip dresses and wrap dresses.

Simple crew neck or vneck sweaters have a place in this wardrboe.

Classic outwear includes trench coats, a fitted denim jacket, and wool coats.

Footwear includes basic pumps, flats, loafers, and sneakers.

Jewelry is simple and minimal. That’s not to say that someone with classic style would not wear a statement piece. Instead, one piece would be the focus, instead of lots of jewelry and accessories. As Coco Chanel said “before you leave the house, look in the mirror and remove one accessory.”

Gold or silver hoop earrings are classic style earrings. Stud earrings are another great choice for classic style. Let’s not forget about pearls. Some simple pearl stud earrings and a pearl strand necklace will always be in style.

A great pair of statement sunglasses might be all the accessory you need to finish off a look. Jackie O and Audrey Hepburn made sunglasses iconic.

Structured handbags like satchels tend to be more classic than slouchy, soft bags. A crossbody saddlebag is also a good choice for classic outfits.

Handbag choices will also be in neutral colors that go with everything. This is another area where quality will be key in timeless style.

While many people don’t wear a watch for function anymore, a traditional menswear inspired watch will always be part of classic style. A watch can be as much of an accessory as a necessity.

A simple belt is another accessory that lends the polished look to outfits that timeless style possesses.

Classic Outfits to Wear Again and Again

Classic pencil skirt outfits

Pair a blouse in a classic pattern with a pencil skirt in a neutral color.

Here a mauve pink snakeskin print blouse was paired with a grey pencil skirt. Colored pumps were chosen instead of black or grey but they are a darker burgundy shade that compliments the mauve.

classic pencil skirt outfit

Pair a leopard print pencil skirt with an ivory shell and camel blazer for a chic work look. Finish the look with classic black pumps.

leopard print skirt and camel blazer classic style

Make that same pencil skirt a chic casual outfit for a brunch or shower with a denim jacket and sandals.

A saddlebag works for a purse here in a classic cognac color. The saddlebag is less formal than a satchel would be but still carries the structure of classic style.

pencil skirt and denim jacket

Blazer outfits

The same camel blazer from above polishes up a casual jeans outfit of jeans and a button up gingham shirt. Leopard flats and the same saddle bag compliment this outfit.

camel blazer with jeans

shirt- JCrew Factory; blazer- JCrew Factory;

Are you seeing a pattern emerging here?

Classic clothing pieces can be worn in different ways for different occsaions. Both the camel blazer and the leopard pencil skirt have been worn in business and casual outfits.

Pair a black blazer with a black and white top and olive pants.

Olive is another great neutral color to have along with black, navy and grey for classic outfits.

Loafers and a snakeskin purse finish this look.

classic style with black blazer

Take the black blazer from work to weekend by pairing it with a classic striped tee shirt and grey jeans.

black blazer with striped tee

Button up shirt outfits

A button up shirt is a classic piece. A white button up is hailed over and over again as a must have wardrobe item. A button up shirt in any color or classic pattern will stand the test of time.

Kellyann at This Blondes Shopping Bag pairs a black button up with polished dressy black shorts and her very classic cap toe pumps. Note the classic gold hoop earrings and quality handbag.

Kellyann’s outfit works for spring in spite of being black because timeless pieces transcend even seasons. They can be worn year round, even in black.

all black and camel outfit classic style
Image source

Beth at Style At A Certain Age pairs a light cream button up with linen pants for a very striking outfit. Cap toe pumps also complete the this look. Notice the classic accessories we discussed before- sunglasses and a belt, both essential to polishing off this look.

classic style cream outfit
Image source

How to keep a classic wardrobe from being boring

Think classics are boring? Think again. It’s already clear that classic pieces can be worn many different ways in many different outfits.

One way to keep classic looks interesting is to add texture.

Here Beth adds texture to a classic sheath dress outfit with a tweed jacket. Tweed is another timeless piece. Wear it dressed up or wear it with jeans.

classic style with texture
Image source

Make a pencil skirt oufit more interesting by wearing the pencil skirt in leather or faux leather. Everything else is neutral and clean. The leather skirt is the star of the show.

leather skirt

Another way to add interest is to add a pop of color.

Accessories are a great way to add color without going overboard or if you just aren’t comfortable with a lot of color.

Here a scarf with pops of red accents a blue stripe button up, classic ankle trousers and a trench.

classic outfit with button up shirt

A white button up and light grey pants get a boost with a red belt.

classic work wear

How to keep classic looks from becoming dated

Don’t focus on trends.

Trends will quickly become dated. It’s fine to add a trend here and there but these are not the basis of a classic wardrobe.

Update and upgrade when necessary.

Some pieces will become dated. A blazer is always classic but your 1970 corduroy blazer probably needs to be updated with a more modern color and more modern corduroy fabric.

Know what works for you and stick to it.

Know how to dress your body. Dressing according to your body type will always yield a classier look than dressing for your age.

If we focus on that number as we age, we can quickly look outdated and frumpy. That doesn’t mean we should try to dress like we are still 20. That won’t work either. We don’t have the same body we had at 20. Dress the body you have now regardless of your age.

Where to shop for classic clothing

You can find classic pieces at almost any retailer but remember to shop for quality when shopping. These retailers offer classic style with quality at affordable price points.

Nordstrom Nordstrom offers styles for all style personalities, but classics are plentiful at a wide variety of prices.

Ann Taylor One of my favorites for work wear.

Loft A sister company of Ann Taylor with looks that have spanned decades. Another go to for me for work wear and for jeans.

JCrew and JCrew Factory- Linen/ cashmere- you can find those here. I often shop JCrew Factory for blazers and fun button up shirts or classic prints like stripes and gingham.

Banana Republic Another go to for blazers, button up shirts and other classic pieces.

Boden The predecessor to online shopping. Johnny Boden started a mail order catalog for things that could be delivered to your home. His catalogue had eight menswear pieces. It’s evovled into clothing for the whole family.

Everlane “At Everlane, we’re not big on trends. We want you to wear our pieces for years, even decades, to come. That’s why we source the finest materials and factories for our timeless products— like our Grade-A cashmere sweaters, Italian shoes, and Peruvian Pima tees.”

For more inspiration check out these other bloggers with impeccable classic style:

Fashion Jackson

My Chic Obsession

Classy Yet Trendy