Top 10+ Questionable Things To Wear On A Date & 10 That Will Make You Stand Out

Wardrobe Rights & Wrongs

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

Your outfit speaks before you even say hello. Getting dressed might seem straightforward, but certain choices can instantly kill the mood while others make you absolutely unforgettable. Well, the difference between looking amazing and looking questionable often comes down to simple awareness about what works for you and what doesn't. So, here are 10 clothing mistakes to avoid and 10 options to definitely try.

1. Wrinkled Shirt

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

Picture walking into a restaurant where every detail matters—the lighting, the ambiance, the first impression you make. A wrinkled shirt immediately broadcasts carelessness, suggesting you don't value the occasion or your date's time. Even if it is otherwise nice, wrinkles undermine its appeal.

2. Strong Cologne

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

Your nose becomes blind to your own fragrance after just fifteen minutes, which explains why some people douse themselves in cologne before dates. This overwhelming scent can trigger headaches and actually masks the natural pheromones that play a critical role in attraction.

3. Flip-Flops

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

Beyond the obvious disrespect for venue dress codes, flip-flops create awkward slapping sounds with every step you take. Most upscale restaurants will turn you away at the door. They also expose feet that may not be well-groomed, further detracting from your overall look.

4. Stained Clothing

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

Restaurant lighting has a cruel way of magnifying even the most minor stains, forcing your partner to focus on that coffee spot rather than your sparkling conversation. Stained clothing indicates poor hygiene habits and a lack of attention to detail—two essential qualities.

5. Pajamas

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

Even luxury loungewear designed for comfort looks completely inappropriate outside your home environment. You'll spend the entire time feeling underdressed and self-conscious, while making other diners and staff uncomfortable in public settings. This choice signals that you put zero effort into dressing.

6. Ripped Jeans

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

Jeans with large holes or that have been torn extensively may appear unprofessional, especially during a first-time meeting in a more formal setting. Moreover, the rips can get caught on chair edges or table corners, causing weird tugging nobody would like to see.

7. Sunglasses Indoors

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

Celebrities are frequently criticized for wearing sunglasses indoors, and there's a good reason why this behavior seems so off-putting. Eye contact builds the foundation of trust and genuine interest between two people. Some folks report feeling "shut out" when their companion keeps their shades on.

8. Workout Clothes

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

Athletic wear is specifically structured for sweating and physical exertion, not for intimate conversations over candlelit dinners. This clothing choice shows a fundamental inability to distinguish between appropriate contexts, making you seem as though you're planning to leave early for the gym.

9. Offensive T-Shirt

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

Other diners and restaurant staff will judge you negatively before you even reach your table, creating an uncomfortable atmosphere. What you find hilarious might deeply offend someone else, especially a shirt saying "I'm with stupid," which rarely lands well in romantic settings.

10. Baggy Suit

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

Baggy clothes, including suits that are too large, tend to look unkempt. They fail to flatter your body. Comfort matters, but not at the expense of fit. While you want to feel comfortable, overly loose or oversized suits can sacrifice style.

Enough with the fashion disasters. Here's how to actually nail your date night look.

1. Statement Necklace

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

Quality jewelry naturally becomes a conversation starter, giving your date something interesting to notice and comment on. A well-chosen statement piece catches light beautifully and draws positive attention directly to your face, creating a focal point that enhances your natural features. 

2. Midi Skirt

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

Flowing fabric brings graceful movement when you walk, adding an element of feminine elegance. This flattering length works beautifully for multiple body types and various venue choices. You can pair midi skirts with heels and a decent top for formal outings.

3. Chino Pants

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

Want to retain a polished appearance? Here comes Chino pants that seamlessly bridge casual and semi-formal occasions. With the right fit, color, and complementary pieces like a button-up shirt or polo and stylish shoes, these pants help you look confident and well-dressed.

4. Blazer

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

A blazer is an excellent option for such a meetup because it strikes the perfect balance between casual and polished, helping you look put-together without seeming overdressed. Choose unstructured blazers in lighter fabrics like cotton, linen, or seersucker for warmer weather.

5. Ankle Boots

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

These versatile shoes go well with dresses, skirts, or pants, offering more visual interest than those boring basic flats. Ankle boots add subtle height without the foot pain associated with high heels, allowing you to focus on conversation rather than aching feet. 

6. Silk Blouse

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

Silk blouses have a natural sheen and smooth texture that elevates your look instantly. Females can wear a silk blouse tucked into fitted trousers or a skirt for a formal or business-casual date. High-quality silk blouses also tend to resist wrinkles.

7. Wrap Dress

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

The wrap design cinches at the waist, accentuating curves and crafting an hourglass shape, which is universally flattering for many body types. For a romantic dinner or special event, opt for a silk or satin fabric in bold colors like red or classic black. 

8. Knit Sweater

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

Brilliant for cozy date venues like wine bars or intimate cafes, knit sweaters suggest warmth and approachability that invite closer conversation. The inviting texture feels comfortable while remaining stylish enough for romantic settings. You can accessorize with scarves, boots, or subtle jewelry.

9. Monochrome Matching Sets

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

These coordinated outfits photograph exceptionally well under most lighting conditions, making them great for dates where you might take pictures together. Matching sets are currently trending in minimalist fashion circles. They offer low-effort, high-payoff styling that shows intentionality and clean aesthetic sense.

10. White Shirt

1. Wrinkled Shirt, 2. Strong Cologne, 3. Flip-Flops, 4. Stained Clothing, 5. Pajamas, 6. Ripped Jeans, 7. Sunglasses Indoors, 8. Workout Clothes, 9. Offensive T-Shirt, 10. Baggy Suit, 1. Statement Necklace, 2. Midi Skirt, 3. Chino Pants, 4. Blazer, 5. Ankle Boots, 6. Silk Blouse, 7. Wrap Dress, 8. Knit Sweater, 9. Monochrome Matching Sets, 10. White Shirt

This timeless piece works for virtually any date scenario, whether it's a casual coffee meeting or a dinner reservation, making it the ultimate versatile choice for men. The classic color complements every skin tone beautifully. You can style white shirts up with blazers.