The Love Coach

Deciding what to wear on your first date is tough. Especially if your first date falls during the colder months. We’re here to help you resist the temptation to pull on some pilly, hole-y, stinky holiday sweater by showing you just how horrible you might look on your date. Read below for our list of 100 types of sweaters you should completely avoid wearing on your first date.

Top 10 Deal Breakers

If your sweater meets any of the following qualifications, it’s the wrong choice.

1. Anything that sheds: If you’re leaving behind bits of pistachio-colored wool or mohair behind you, no one’s going to want to risk kissing or even hugging you goodnight.
2. A stinky sweater: Sometimes we wear our sweaters more than once without washing or dry cleaning them, but if it’s a first date, always wear a clean–or at least Febreze’d–sweater.
3. Anything the moths have gotten to: If you find a hole under your armpit, don’t think that no one will notice. They will.
4. Anything that smells like mothballs: Keep your sweaters in airtight containers during the summer months. Mothballs will make your first date gag.
5. "Vintage": Vintage sweaters are cool but not for first dates. Especially if your idea of vintage is a triple hand-me-down from your great grandpa who loved to sleep in his sweater.
6. Stained sweaters: Wearing a stained sweater to your first date–no matter what kind of stain it is–makes you look disgusting and lazy.
7. Cashmere: Cashmere is soft and snuggly, but it’s also really hot and will probably make you sweat if you’re even the teensiest bit nervous.
8. Horizontal stripes: Girls who wear sweaters with horizontal stripes will just look chunky, so wear something more flattering.
9. Itchy sweaters: If you’re going to be itching and scratching and turning red during dinner, wear something underneath or pick a different sweater.
10. Incredibly expensive sweaters: You’ll be so nervous that you’ll end up spilling something on it, but you can’t make a big fuss because you won’t want to seem materialistic or rigid. Leave it at home.

Characters and Cartoons

Wearing a sweater that has a picture of a character or cartoon character on it will make you look silly, immature and dorky. Move on.

11. Harry Potter: Dressing like Harry Potter on your first date translates into one thing: you have no life.
12. Disney Princesses: Most everyone over the age of six thinks that the whole Disney Princesses thing is lame, so give this one to your niece.
13. Mickey Mouse: Just because a handsome model from Saks is wearing it, doesn’t mean it looks good.
14. The Smurfs: The Smurfs didn’t even wear sweaters, so wearing a sweater with a picture of a Smurf is just illogical.
15. Velma: Velma was the brainiac from Scooby Doo, and no one wants a first date with a brainiac.
16. Charlie Brown: Charlie Brown stands for inferiority and social inadequacy. Is that what you want to communicate to your date?
17. Spongebob: We could have showed you a Spongebob sweater on a human, but then you might not have gotten the true horror of its potential. Don’t wear this.
18. Curious George: A picture of a naked monkey won’t get you very far in the goodnight-kiss department.
19. Superhero sweaters: Superheros don’t wear sweaters, and neither should you on your first date.
20. Woodstock: Wearing a sweater with pictures of Woodstock on it will make you look flighty, clueless and a little deranged..

Christmas Sweaters

Christmas sweaters are the ultimate in bad sweaters, and while most people know this, sweater lovers continue to wear them unphased. If you wear one on a date, you’ll be the laughingstock of the entire restaurant.

21. 3D Snowman: Christmas sweaters are known for being 3D, and this snowman is just too much.
22. Sophisticated reindeer: Sometimes designers try to turn Christmas sweaters into sophisticated styles, but it’s still all wrong.
23. Christmas sweater vest: As if it couldn’t get any worse!
24. Nontraditionally colored sweater: Just because it’s not red and green doesn’t mean it’s okay. It’s still an ugly 3D Christmas sweater.
25. Garish Nutcracker sweater: This garish sweater is the color of Pepto Bismol and has sparkles and designs on the sleeves, collar and and everywhere else.
26. Santa Claus: Santa would freak if he saw you wearing this sweater.
27. The Bridget Jones Christmas sweaters: Even top barrister Mark looks doofy in this reindeer design.
28. Manger scene: Wear this on a first date and just see what happens.
29. Doggie Christmas sweater: Covered in dogs, paw prints and doggie bones, this sweater is just awful.
30. Gingerbread man: Gingerbread men are for eating, not wearing on a sweater.
31. Teddy bear Christmas: Teddy bears are a dowdy Christmas favorite, but don’t you succumb to the terrible trend.
32. Crafty sweaters: Sweaters that look like they were bought at a country Christmas festival should be off limits.
33. Snowflake sweater: Even a simple design in neutral colors like gray and navy won’t cut it.
34. Christmas tree: It’s a classic Christmas symbol, but it’s not date-worthy.
35. The Christmas dinosaur: This odd design will prompt too many questions.
36. A sweater that has pictures of other sweaters on it: This is the quintessential bad Christmas sweater.

Glitter and Sparkly Sweaters

Every sweater needs a little bling, right? Wrong. Avoid these at all costs.

37. J.Crew glitter sweater: When did J.Crew think it was okay to make something for the roller rink?
38. Homemade sparkly vest: Special glitter thread does not add edge or "that special something" to a sweater vest.
39. Cascading sparkles: This Santa beard is a good example of how the designs on your sweater should not be made out of sparkles.
40. Sequin sweater: Would you go on a date with this guy? Then don’t expect anyone to want to see it on you, either.
41. Pink showgirl sweater: This sweater was made for Lady Luck and no one else.

Slutty Sweaters

Yes, even sweaters can be slutty and inappropriate. If you disagree, then check out these awful selections.

42. Netted cowl neck sweater: Don’t let the cowl neck part fool you. Only a tramp would wear this thing.
43. Cropped crochet vest: It’s weird that a crochet design can look slutty and cheap, but this sweater does the trick.
44. See-through sweater: If your sweater is too thin, put a t-shirt or cami on underneath.
45. Crop top: Never wear a sweater like this without a longer top underneath.
46. Too tight: Too-tight sweaters are not only inappropriate, they also look dorky.

Holiday Sweaters

Holiday sweaters don’t just have Christmas designs. From Halloween to Easter, check out this list of major don’ts.

47. Horn of Plenty: The Horn of Plenty should be reserved for elementary school arts and crafts and the Thanksgiving table, not your date-night sweater.
48. Hanukah Sweater: Covered in gold Stars of David and a menorah, this holiday sweater is a bad idea for date night.
49. Winter scene sweater: When a scene covers every bit of the sweater, you know it’s got to go.
50. Easter scene: 3D chicks and Easter eggs are inconvenient, let alone tacky.
51. Patchwork Halloween sweater: Bats, a skeleton and a black cat? Anyone who loves Halloween that much should stay home.
52. Valentine’s Day: If you’re already expecting your date to be with you on Valentine’s Day, he’ll be freaked out by your intensity.
53. The flag sweater: The flag sweater is a staple for the 4th of July and Memorial Day, but wearing it on a date makes you look lazy.
54. Thanksgiving turkey: A puffy turkey and puffed out pumpkins will not impress your date.
55. Kiss Me I’m Irish: If you find this design on a sweater, save it for St. Patrick’s Day only. Wearing it on a date will make you look crude and tacky.
56. Halloween fringe: Who’s going to take you seriously in this?

Teacher Sweaters

Teachers get a bad rap for their sweater choices, but that’s not your fault. Resist the temptation to take style choices from your third grade social studies teacher and wear something a little sexier.

57. Drapey boring sweater: It’s navy, has a few 3D designs and is much too long.
58. Roosters: This oversized rooster sweater is a total miss.
59. Happy Hearts sweater: Just the thing a kindergarten teacher would wear, not you.
60. The apple sweater: How stereotypical is this? You shouldn’t wear it on the first day of school, let alone your first date.
61. School symbols cardigan: Do you want "school symbol appliques and…sparkling rhinestone accents" hanging off your body when you lean in for a kiss?
62. Dogs cardigan: Great for the teacher who loves dogs, this sweater will send your date running.
63. Cat sweater: Teacher sweaters and cat sweaters are annoying and a little creepy.
64. Sweater vest: Nothing says stuffy professor like this look.
65. Book stack mock-neck sweater: We’re not sure what’s worse: the book stack design or the fact that this is a mock-neck sweater.
66. 123, ABC: Your date probably already knows his ABCs, so spare him the lecture.

Grandma and Grandpa Sweaters

Sometimes dressing retro is cute, but there’s a right and a wrong way to do it. Avoid these old-fashioned and conservative designs.

67. The capelet: What’s a crocheted capelet? This. And it’s unacceptable date wear.
68. Grandpa or Grandma’s old college sweater: Especially if it was from an Ivy League, this choice will make you look like a pretentious bore.
69. Victorian puffed sleeved sweater: This chunky, bow-tied mess is not sexy at all.
70. Grandma hug sweater: Actually, this cardigan could be worn by either grandparent, a clear indication that it’s not right for your date.
71. Sailor sweater: People who wear sailor sweaters on dates probably have nothing better to talk about than topsiders and sails.

Too-Conservative Sweaters

No one wants to look like a prude on their first date. Avoid these too-conservative sweaters.

72. 1950s sequin sweater: This is a pretty design, actually, but it’ll make you look too innocent for a first date.
73. Sunday School teacher sweater: Do you want to date any of these people?
74. Convent sweater: Does it look like a nun would wear it over her habit? Toss it.
75. Rose-colored beaded sweater: The color combination, beaded design and overall fit are just too conservative.
76. Argyle: Argyle is okay for work and school, but not for a first date.

Handmade Sweaters

A handmade bracelet or necklace is okay on a first date, but never a handmade sweater.

77. Crochet wrap sweater: Even the tailored design can’t trick us: this thing is crochet and not date-worthy.
78. Hand-knit fringe: This sweater was actually made in Ecuador, which is nice, but it’s still too crafty for a date.
79. The unfinished mess: If it looks like garbage, don’t bother finishing it.
80. The sweater you bought at a fair: Cute in the ramshackle tent, not on you.
81. Tie-dye sweater dress: Don’t get any ideas to DIY your sweater dress into a tie-dye nightmare.

Avant Guard Sweaters

Even truly daring and artistic creations won’t work on your first date. View these examples to find out why.

82. Drapey, deconstructed sweaters: This style will make you look messy and artsy fartsy, but not in a good way.
83. 1980s abstract sweater: This sweater says that you love color and aren’t afraid to show it.

Colors to Avoid

From pea to leopard to rainbow, these colors do not work on sweaters.

84. Pea and pistachio: If it reminds you of vomit, it’s probably not a good choice
85. Bright orange: A bright orange sweater on your first date? See Velma from Scooby Doo, above.
86. Multi-colored or rainbow: A sweater with crazy patterns and lots of different colors will be too distracting for a first date.
87. Leopard print: This is sometimes considered a glamorous print, but it looks horrid on a wool sweater. Especially for a first date.
88. Mud: If you wear brown, make sure it’s a rich color that enhances your complexion.
89. Anything faded: If your sweater has been through the laundry too many times, opt for something brighter and newer.

More Bad Choices

Our final list includes even more bad sweater choices, including the hoodie, sleeveless sweaters and Mr. Rogers sweaters.

90. Anything that was made for a dog: The dog even looks miserable, and you will too.
91. S&M sweaters: Not only will you not be able to eat or shake hands, you’ll probably scare off your date in seconds.
92. The hoodie: If you still need an explanation, then you are probably wearing a hoodie right now.
93. Sleeveless sweaters: You can show your creative styling by layering under this sweater, but it’s still a bad choice that would only pass on toddlers.
94. The 80s sweater: If you wear this, your date will think you’re from a small town in Eastern Europe..
95. The sweater you wore for picture day in sixth grade: Bad choice all around.
96. Military sweater: This is kind of an intense choice for a first date.
97. Suburbanite: This sweater’s been named "Suburbanite," and we don’t think that’s a good sign.
98. Hate messages: Any sweaters that proclaim hateful, racist or sexist messages are a definite don’t.
99. The Mr. Rogers sweater: For old people in their chairs.
100. Team sweater or jersey: This fashion choice suggests you’d rather be at home watching the game than putting any effort at all into looking nice for your date.

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