The Do's and Don'ts of Dressing For A First Date

Dressing for a first date

Here are some specific things to consider before your date and maybe some things you wouldn’t have thought.

“Tis the season of love and the stores covered in chocolates, hearts, red and pink, and flowers either taunting you or building excitement. As a personal styling company giving love advice or making that unique someone notice you so you can finally get that first date is not our area of expertise. What we can do though is help you take the stress out of getting dressed for that special day. 

Remember, your first date is your first impression whether it’s a blind date or you’ve always known the person. This is the first time you guys get to know each other one-on-one without any distractions, hopefully. Because of this, you want to make sure you dress like yourself. You don’t want the person sitting across from you to be the victim of false advertisement. Don’t wear a three-piece suit to your dinner date if you’re a laid-back approachable type of person. Dressing like someone else will not only make you feel uncomfortable causing you to feel awkward during the date but it will also lead to problems down the road, since who you showed you were is not who you actually are. 

Dressing in comfortable clothes you feel good and confident in needs to be emphasized. If you’re fidgeting throughout the entire date, it can appear that you aren’t enjoying your time and make the environment between you and your date awkward. Do your best to avoid purchasing a brand-new outfit for your date. You haven’t fully tested the garment out and won’t know how it stands up to sweat, a big meal, a lot of walking, etc. 

Be sure to dress according to the date’s activities. If there’s going to be a lot of walking, then make sure to wear the appropriate shoes. Unless it’s going to be a dusty hike, a clean pair of sneakers will work just fine. If the date consists of a hike or super strenuous activity, then wear a shirt that compliments your skin tone well and try a cute, yet casual updo. Wearing your best colors will brighten your skin, making you look more radiant and attractive. And please avoid wearing your raggedy gym shorts. Just because it’s a sports date doesn't mean you should look run down. 

Accessories are a great way to spice up your date outfit as well. Dawning statement jewelry can be a great conversation starter, and keeping in line with a workout shirt, make sure the colors you wear for jewelry are complementary. If you have warm undertones, wear gold. If you have cool undertones, wear silver. And make if you decide to rock blues, reds, or any nonmetal colors they are within your color palette. This will dry your date’s attention to your face. However, wearing a hat that covers your eyes will do the opposite. As the saying goes, eyes are the windows to the soul. You don’t want to make it hard for your date to make a connection with you by covering one of the most important parts of your face. 

Denim is a great way to dress your outfit down without looking too casual. But if you’re going to wear denim, make sure it’s your most flattering pair of jeans. A good pair of denim with a feminine, eye-catching top and a pair of heels is an easy, comfortable go-to for any woman. Or if you want to break out a dress, adding a fitted denim jacket with heels can have a similar effect. For the men, pairing your best jeans with a sports jacket or blazer and a clean, well-fitted t-shirt or button-down with sneakers or dress shoes is an easy, sleek go-to. Depending on the location and your personal style will determine how much you dress your denim up or down. 

Last but certainly not least, be sure your clothes fit! This happens time and time again when people believe wearing loose clothing will hide their weight. But the only thing it’s doing is making you look bigger than you actually are, giving you absolutely no shape. Dressing in your correct size and for your body type is 10x more attractive because it not only flatters your body the best but signals to your date that you are confident in the skin you’re in and know exactly how to work it to the best of your ability. 

The best thing you can wear for your date this Valentine’s Day is your confidence, putting your best self forward. That means knowing what looks good on you when it comes to the colors and fit of your clothes. Hiding behind a hat or trying to dress as someone else is not how you’ll find the one. Showing you’re comfortable in your most flattering hiking clothes and being smart enough to not wear comfortable shoes if you know you will be walking through the city are things that will help you, not harm you. Knowing how to properly dress up and dress down denim can be a tricky one, but contrary to popular belief, not everything goes with jeans – most things, but not everything. As personal stylists, it’s not the first time we’ve helped someone navigate the trenches of getting dressed for a first date and eventually finding love because of their new look. So, if you’re ready to gain the confidence you’ve always wanted and put your best foot forward on your next date, seek help from a personal stylist.