This post will only talk briefly about what NOT to wear. What you should wear is a very open-ended topic. What looks good on me, may or may not look good on you. However, there are some things that rarely look good on a first date. First impressions matter- not as much as who you really are- but even the best-of-men can come off as sleezy, disheveled, or just plain dull.
Below are just some suggestions. If you are a working professional, perhaps it would be good to seek a fashion consultant or a friend who has good taste (usually these friends are women or on occasion gay men).
1. Bright colors. Pink, red, orange, turquoise, anything shiny. Who you are should be the focus, not that shirt you’re wearing. Women notice these things and unfortunately when it’s not a good thing, she’ll tell all her friends and they will surely all respond with “eww” and then with LOL. Normally, I couldn’t care less if a woman made fun of me and I would tell you not to worry, but in this instance, let’s be a little more mindful. Some people say that wearing bright colors shows you are confident, not if that shirt makes you look like a douche, cause then you would be a confident douche. Let your confidence shine through your words, your attention to her (and not you), and your actions (e.g., open doors, pull out her seat for her to sit, etc.)
2. Work clothes. Enough said. Don’t even argue with me on this one. I once saw a guy go on a date in his scrubs (he is a physician). If you are too busy to spend 10 minutes to change clothes, you are too busy for a date. Women will prepare regardless of how busy they are. They even risk their lives to do so (i.e., driving and putting on make-up at the same time). Show her the same effort and appreciation. She won’t say it, but she’ll appreciate it. You can subtly let her know too by saying how you didn’t have much time to change but wanted to look somewhat appropriate for this date. Trust me. Brownie points +10.
3. Work shoes or grandfather shoes. Shoes are by far one of the most, if not THE most, important accessory for women. She’ll notice yours. Don’t wear scruff-up shoes, torn shoes (unless they were torn for a reason), or shoes you’d wear to walk your dog.
4. Jacket-less outfit. Try your best to put together outfits that work with some kind of jacket. If it’s summer time, a light jacket. If winter, a pea-coat (e.g., Kenneth Cole and Coach sell some very nice ones). You may not need it, but she will even if she may not be ‘that’ cold.
5. Striped shirts. This one is a shout-out to my friend WW. She abhors striped shirts. I disagree with her on many things, but on this issue, I am in complete agreement. Solid colors only.
6. Flashy belt buckles. Nice, you want a cookie?
7. Loose (or ultra tight) suit jackets, shirts, and pants. I will make a posting about how to choose suits. In the mean time, if you are a working professional, go to a tailored shop to get your suits and sports coats. They’ll cost more (e.g., $200-400 per jacket), but it’ll be WELL worth the cost. DO NOT GO TO Men’s Warehouse. Unfortunately, Men’s Warehouse does not really cater to Asian American males and our body types. Their items are large with large shoulder designs and long (almost draped) coats. Think Snoop Dogg. You’re not Snoop Dogg. If you need some recommendations, please contact me directly and I can direct you to some very good specialty shops in Los Angeles.