How to Look Classic, Not Stuffy

4. Choose a new “wear everywhere” dress

The “little black dress” is legendary for dress-up/dress-down situations. However, many LBDs that worked in the era of high heels, 9-to-5 corporate clothes and shape wear look dated today. Instead, try a below-the-knee midi in a wrap or A-line and shirtdress styles to fill the gap and wear with anything from a modern sneaker to sandals to flats. Though black always works, try a floral, animal print, a warmer neutral such as brown, tan or olive or even a classic red as an alternative. It’s the dress you’ll wear to run errands, work from home, wear to the office or out to dinner.

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Clockwise from left: Gap Linen-Cotton Blazer in Rose Crystal Pink ($128, gap.com); Rothy’s The Flat in Bright Red ($129, rothys.com); Artisure Women’s Classic Leather Penny Loafer Drivers in Red ($41, amazon.com); GH Bass Women’s Weejuns Whitney Exotic Penny Loafers in Emerald Croco ($165, macys.com)

Gap; Rothy's; Amazon; Macy's

5. Add color to energize clothes

Neutrals such as black, navy, gray and beige are the backbone of a well-considered wardrobe, but a steady diet of them day after day can be boring. Classic fans often resist color, but all you need is one pop to give a spark to a basic look. The key is to stick with classic styles. Shoes are the simplest entry point, so try loafers, loafer mules or flats in a primary red or green. For an even bigger update, select one of your favorite and most-worn items of clothing — a blazer, cardigan or skirt — and try it in a color you love. Hint: makeup shades in pinks, corals and reds are always flattering.

(Left to right) Naomi Watts, Gabrielle Union and Sharon Stone

Bruce Glikas/Getty Images; Matt Winkelmeyer/Getty Images; Marc Piasecki/FilmMagic

6. Tweak your hair, makeup and sunglasses

Bobs are back, red lipstick looks brand new, and aviators could not be hotter. These are all classics reinvented for 2023 that can amplify your style efforts and are worth another try. (FYI: A “box” bob is the trendy new name for a classic, blunt, chin-length bob — which is still one of the ultimate “fatteners” for thin, fine hair.) All variations of the bob from wavy to shaggy to textured are super-chic. Red lipstick comes in a vast array of shapes and containers from the classic bullet to chubby pencils, tinted balms and liquid lips in a tube with a sponge applicator. Choose a texture and red hue that resonates for you from sheer to full strength. Finally, invest in an updated pair of aviator sunglasses with angular or oversize teardrop frames. Who says you can’t be classic and trendy?