10 Classic Clothing Pieces

You hear about “classic” cars and “classic” movies, but what, exactly, is “classic clothing?” Old styles from long ago that were hot in their heyday but that no one wears anymore?


Classic clothing are styles that look good on just about everyone and that have been popular for years. Like the humble chicken that can be batter dipped and fried for a casual occasion or simmered with vegetables into Coq Au Vin for formal guests, classic clothing can be dressed up or dressed down for any occasion. With classic pieces, a little can go a l-o-n-g way, so invest in these wardrobe staples so you can wear them for years to come.

Classics include:

White ShirtA Crisp White Shirt

A crisp, white, button down shirt can be worn under suit jackets, with a skirt or pants, under a vest, over a tank top whatever you want. Dress it up with a silk scarf or a strand of pearls for work, or tuck it into jeans for a more laid-back look.



Form-fitting teeA Form-Fitting T-Shirt

A simple style, form-fitting t-shirt can take you to meetings when worn under a jacket, to a picnic when worn with jeans, and help keep you warm when layered under a shirt or sweater. Forget the logos, cute sayings, or goofy details – just stick with white and fitted for maximum versatility.



Straight leg dark pantsStraight Leg Dark Pants

Dark, straight-legged pants in a simple style can take you to work during the day, to evening events at night, and to casual events on weekends, depending on what you pair with them. Dress them up with a beaded top and sandals for night, dress them down with a sweater and flats for errands.



Straight leg jeansStraight Leg Jeans

A simple style, straight-leg dark denim jean can see you through LOTS of casual activities. Pair them with a silk top and heels for something a little dressier, a t-shirt and tennis shoes for something a little more casual.



Single breasted jacketA Dark, Fitted, Single-Breasted Jacket

Want to command respect and immediately set a more formal tone? Put on a dark, fitted, single-breasted jacket. It’s appropriate for meetings, funerals, church – you name it – and will immediately upgrade any outfit you wear, including jeans. If you can only afford one jacket, make sure it’s this style.



Knee-length skirtA Knee Length Skirt

Whether your lower half looks best encased in a straight, A-line, or wrap style, strive for a dark or neutral color with a hem to the knees. Knee-length tends to flatter most women, whereas thigh high or calf length tend to work for very few.



Day dressA Day Dress

A day dress in a simple style can take you just about anywhere, from church and teas to funerals and work. You can dress it up with heels and jewelry, dress it down with flats and a trendy jacket.



Cocktail dressA Cocktail Dress

This can be the traditional LBD (little black dress) or another color in an evening style and fabric. Wear it for cocktail parties, semi-formal dinners, drinks with friends, or the theater.



Trench coatA Trench Coat

A classic, belted trench with a zip-out liner can take you anywhere in the world three seasons a year. It will repel rain, sleet, and snow in style, and fold up compactly when not in use. Originally designed as an all-weather coat by Thomas Burberry for use by British soldiers “in the trenches” during World War I, the trench does exactly as intended – keeps you warm in all sorts of weather.


Walking shortsWalking Shorts

A dark or neutral-colored, flat front, straight-leg walking short is a summer staple. It should fit you properly without gaping, pinching, or riding up, and the hem should hit just a few inches above the knee. Wear them with tennis shoes for a very casual look, or upgrade a bit with strappy sandals or cute flats.


All classic clothing in this section from

Now I have to admit that if I’d seen this list at the height of my clothing consumption (“fashionista”) days in my 20’s, I would have shouted, “boring!” and immediately dismissed it.  But take a closer look at these clothes. They look great all by themselves, but they also offer an elegant background to more interesting pieces.

Have a stunning top you want everyone to see? Pair it with your black pants or dark skirt. Have a gorgeous new necklace? Put it with your classic day dress and show it off properly.

It’s like the difference between walking into a white room with light blue carpet and being asked to set it for an elegant dinner party on a $500 budget, and walking into a lime green room with orange carpet and being asked to do the same. The first one allows you to focus on the table; the other forces you to cover up the backdrop before taxing your imagination (and what’s left of your budget) on the table. See the difference?

Yes, trends are fun and certainly have their place, but classic clothing pieces are VERSATILE and allow you to do more with less. Dress them up, dress them down, wear them out – and still look good. That’s the power of classic pieces, and that’s why you should have plenty of them in your wardrobe.

Need more help finding classic clothing pieces that work for you? Download a copy of Wardrobe Magic to see how easy dressing well can be. Wardrobe Magic


  • Debbie

    Reply Reply July 23, 2009

    I agree, you need to have the basics covered and then add “of the moment” touches as they may apply to your life style. I did notice that you suggested putting the jeans with heels on one occasion and tennis shoes on another. I think the difference in length would make this hard to do. I know if I want to wear the same pants with both flats and heels, I have to buy two identical pairs and have them hemmed accordingly.

    • Diana

      Reply Reply July 28, 2009

      Hi Debbie,

      You’re right — I should have qualified that comment. I do have two lengths of jeans, one for heels, one for flats, but I can also flip up the (very) wide hem of the longer pair to create a cuff and wear them with flats. Thanks for the note!


  • Kristine

    Reply Reply July 23, 2009

    Thank you, I really enjoy your tips. I’ve searched for over a year for the perfect white shirt, but still haven’t found it. The shirt you show is very close, but sold out! You could probably write an entire article on what makes the perfect white shirt (realizing that this will be slightly different for different women) and where to find it!

    • Anonymous

      Reply Reply November 22, 2009

      I had the same problem – finding the perfect white shirt. However, I recently attend a “CABI” home show and found what I’ve been looking for. The front and sleeves are crisp but the sides and back are knit. It fits wonderfully and can be worn alone or under a jacket with no bulkiness. The price was approx. $85.


  • Cheryl

    Reply Reply July 23, 2009

    Great list! I agree except for one thing- I just can’t stand the look of walking shorts on me. I own them, but never end up wearing them- I tend to have a ‘formal’ looking build, and they just look too sporty. I’ve substituted a pair of black cotton flood pants, which look casual but not suggestive of sport, and can be worn with sandals or tennis shoes. Any other alternatives?

    • Diana

      Reply Reply July 28, 2009

      Hi Cheryl,

      This is just a general list. If you don’t like the way shorts look on you, then by all means, opt for Capris. I know a lot of women who prefer longer lengths because they don’t like how they look in shorts. Do what makes the most sense for you.


  • bolatito

    Reply Reply July 25, 2009

    hi diana, i just want to say a huge thank you for changing my fashion sense.u are the best!i must confess that your note on the 10 classic pieces is an eye opener for me.don’t have an idea of what a cocktail gown should look like because i have never attended one.i know what to get now and will definitely do before my next invitation..thanx a bunch!

    • Diana

      Reply Reply July 28, 2009

      Hi Bolatito,

      Obviously, you need to get the pieces that suit your lifestyle best, but a classic cocktail dress will take you to so many after-five functions in style that if you do typically attend evening events, you should have at least one in your closet. If you don’t, then don’t worry about it. Spend your money on the clothes you wear the most.


  • Julia

    Reply Reply March 14, 2010

    I should love a pair of shorts or capri’s that I look good in – I am a pear shape with heavy legs, dreadful knees 5’9″ but possibly a bit overwieght (not excessively so). I find anything above the knees makes my legs look dreadful and capri’s make my legs look short. All the mums on the playground wear them and look fab I’d love to joing them – any suggestions please? Why don’t they suit me?

    On an alternative note – I’ve finally acquired a crisp white shirt – bought 2nd from ebay after quite a search – fitted with a formal cuffed sleeve – its nice too 🙂

  • FG

    Reply Reply August 28, 2010

    Great tips! I got some shopping to do. Thanks.

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