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Date Outfit Ideas: 5 Dresses Perfect for Any Season

A woman wearing a flower dress from one of these date outfit ideas.

Anyone who has ever gone on a date knows the struggle of that What do I wear?! moment. Well, end your wardrobe wondering with these date outfit ideas centered around five dresses for your next big date night.

Why start with a dress? Not only are they easy to throw on, but they’re comfortable, too—and when it comes to dating, comfort is key. The last thing you want to be doing on a date is adjusting your pencil skirt, gasping for air because your jeans are too tight, or covering your stomach as you dare to bare it in a crop top. Dresses require minimal effort and come in plenty of styles to fit and flatter most women, regardless of their shape or size. I’ve never put on a dress and felt anything less than fabulous, and neither should you!

The key is investing in items that are functional and can be styled differently throughout each season. To find unique styles on a budget, try consignment shops and online thrift stores like—you’re bound to score something that will make you stand out. Look for dresses that work year-round so you get the most bang for your buck. With the right accessories, most dresses can transition from day to night or summer to fall, which lets you spend more time with your date and less time with your closet.

Here are five date-worthy dresses every girl should have in her closet:

1. A printed mini dress.

A flirty mini dress, whether it features a simple star print or colorful stripes, screams cute. It’s effortless, it’s playful, and it’s fun. In the summer, pair it with white sneakers and a jean jacket for a day of riding bikes and eating ice cream. In the winter, wear it with sheer tights, a textured cardigan and ankle boots for a shopping date downtown. Best of all, you can find one at any price point because printed mini dresses are currently a popular trend.

2. A midi slip dress.

Not to be confused with a mini dress, a midi dress hits between your knee and your ankle- commonly known as “tea length.” Choose one with a slip silhouette, and you have a dress that will be turning heads. Whether you dress it up or down, it looks as sophisticated as it does sexy. Pair it with tennis shoes for the farmer’s market, platform heels for a dinner party, or a blazer and loafers for a day at the museum. For those cooler nights, throw on a longline cardigan to keep the look chic and streamlined.

3. A black maxi dress.

People tend to think of summer when they hear the words maxi dress. However, if you buy a maxi dress in a dark, solid tone, it can serve as a blank canvas throughout the entire year. Use it as a quick cover-up at the beach or make it the star of the show with statement earrings and a fun bag. When the weather turns, add studded boots and a leather jacket for a laid-back vibe perfect for attending a concert or late-night drinks at the bar.

4. A jersey wrap dress.

The best thing about jersey material is that it’s forgiving. Jersey wrap dresses are formfitting and tend to tie at the smallest part of your waist, creating a slender silhouette. They are also extremely comfortable and come in a plethora of prints, patterns, and colors, so you’re guaranteed to find one that you like. Wear one with wedge heels and dainty jewelry to meet his parents, or pair it with stilettos and a trench coat for a dinner date out on the town.

5. A fancy dress.

Chances are you have a handful of sparkly dresses in the back of your closet that never see the light of day. When you’re single, dressing up doesn’t happen too often, but add dating into the mix and your event calendar basically doubles. Invest in a fancy dress you can reach for regardless of the event, whether it’s his company holiday party or a summer wedding. Buy a dress that highlights your assets, in a color that compliments your skin tone and a fit that accentuates your body type. Look for a wear-anywhere dress in a timeless, neutral color that doesn’t require many accessories—a simple heel, a small clutch, and your favorite shade of lipstick. It’s much less stressful to buy accessories that match the mood of an event than to buy an entirely new dress!

In the end, regardless of what you decide to wear, you want to feel comfortable and confident. Be sure to keep in mind the activity, location, and time of day. When in doubt, wear a dress!

When not working as an IT consultant, Allie Lochiatto is a style blogger and model. She writes for her own blog, Allie Wears, and for thredUP, an online and offline thrift store that has an amazing selection of brands and styles, including women’s dresses.

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