A Dress for Every Occasion: Which You Should Wear and When

Searching for a new dress never gets old. There are plenty of choices for every occasion, from a breezy maxi for your next visit to the resort to a chic New Year’s cocktail dress. With all the styles, colors, lengths, and designs you have to choose from, you may be at a loss purchasing a new frock. Don’t worry—we have you covered. While our list of women’s dresses to wear based on the occasion might not be all-inclusive, it’s a start.

Hooded Dress for Self-Care Day

Let’s start with casual pieces, like a hooded dress. Hooded dresses are cozy pieces ideal for kicking back at home. They’re styled like a hoodie at the top, and the attached hood might feature an elasticized edge or drawstrings to adjust to your comfort level. Comfortable materials that these dresses are made of could be French terry cotton, other cotton blends (especially those with a bit of stretch), and velvet. Some dresses may also feature a fleece interior for an extra dose of softness and pockets for warmth. These dresses are okay any time of the year but best for colder conditions, like a cozy winter day.

Styling Tips: While indoors, wear this dress with slippers. However, it’s stylish enough to toss on before running errands. Pair this type of dress with running sneakers and a baseball cap if heading outdoors.

Shirt Dress for the Office and Happy Hour

If you work in person or from your home office, a shirt dress can keep you looking put-together. A shirt dress is an effortless way to step up your style game while still feeling comfortable. That’s because many shirt dresses are made of a comfy material, like poplin, a lightweight, plain-woven fabric usually made of cotton. For commuters, dresses made of this material will keep you cool as you rush to work. Another great thing about shirt dresses is that you can find them in many shades and designs suitable for the workplace, such as neutral tones and pinstripes.

Styling Tips: If you walk, drive, or take public transportation, keep your soles comfortable by matching your dress with cushioned sneakers. Then, once you arrive to work, you can tuck your shoes away in a stylish canvas tote and slide into sandals, pumps, or other dressy shoes. Alternatively, you can wear leather flats throughout the day. If working from home, socks or slippers will do (who will see your feet, anyway?).

Maxi Dress for Your Next Vacation

If you’re planning a vacation, remember to pack a maxi dress. Breezy maxi dresses work for plenty of vacation outings, from a beachside dinner to a day exploring a new city. The design you choose is up to you. However, certain shades and prints are perfect for a vacation, such as white, pastels, florals, and nautical patterns. Additionally, look for dresses with features that can keep you cool, such as cutouts, an open back, and slits.

Styling Tips: If you’ll be outdoors for some time, hats with a wide brim, such as a sunhat, can keep your eyes protected. Speaking of your eyes, rock a pair of designer eyeglasses for even more protection. For chilly evenings, make sure to have a cardigan to toss on for comfort.

Cocktail Dress for a Night Out

Everyone needs that go-to cocktail dress for a night out or special date. A Little Black Dress (or LBD) is the quintessential piece for going out. If you can’t figure out the cocktail dress that looks best on you, the LBD looks good on everyone. However, it wouldn’t hurt to figure out your ideal style that really brings out your personality. If you love bold pieces, find cocktail dresses with allover sequins, a leopard print, or a bright red shade.

Styling Tips: There are plenty of ways to elevate your night out or date look. You can wear jewelry based on your style, like elegant diamond or pearl studs, or eye-catching pieces. Depending on your essentials, you might carry a clutch or designer handbag. As for your shoes, they can make a statement or perfectly match your dress. Have fun accessorizing!

Evening Dress for a Gala

The most formal type of dress on our list, a floor-length evening dress, is ideal for a formal gala. There are various gala dinner events, such as a charity event or auction. These events usually have a black-tie dress code, with many people wearing some of their best, most glamorous pieces. Look for dresses featuring luxurious materials, like satin or silk. However, you can find plenty of stunning dresses without spending more.

Styling Tips: Style your evening dress with tasteful jewelry, such as pearl or diamond studs, or drop earrings. Similarly, match your outfit with a chic clutch and heels.