When it comes to dressing for a first date, the amount of options can seem overwhelming. If you’re looking to make a great first impression on your date, you want to look sharp and feel comfortable. Here are some tips for doing just that:
- Choose colors that work well together. When you have a busy outfit like a suit or dress, choose colors that complement each other. You don’t want your outfit to clash with itself!
- Make sure everything fits perfectly! You don’t want your pants baggy or too tight, or your shirt gaping open because the buttons aren’t buttoned correctly. When in doubt about fit, get it tailored!
- Keep accessories simple and tasteful—don’t overdo it with jewelry or watches! Having too many things going on makes it hard for people to focus on one thing at a time. This is especially true when trying to make an impression on someone new!
DO DARK DENIM
A casual date calls for denim. If you told your date casual, they will most likely be in jeans or a casual dress, so it’s important you stick to the dress code (translation: do not wear a suit). Instead of your relaxed fit or light-wash weekend denim, opt for a dark-wash straight-leg jean. It’s universally flattering and will work with a variety of shirts—plus, the darker wash will lengthen your legs, making you appear taller. Be sure to add a leather belt to your jeans if your shirt will be tucked.
LAYER WITH STYLE AND PURPOSE IN MIND
Use the cooler fall weather to add depth to your date night look with a layering piece. A sporty but elevated bomber jacket, a casual ¼ zip sweater or a classic sport coat gives you a polished, dimensional look without too much fuss.
DATES CALL FOR A COLLAR
A collared shirt is almost always a must for a first date. Unless the two of you are off on a serious sporting adventure, wear a button-up shirt or polo. For a cozy dinner, choose a button-up shirt in a classic print, like windowpane or gingham. Headed to an outdoor concert or a leisurely dinner al fresco? Try a conversational print with a touch of seasonality.
OPT FOR SHARPER SHOES
When in doubt, a dressier shoe is the best option. While oxfords are best saved for suits and suit separates, a Chelsea boot or a derby shoe, for example, will work with dark-wash denim or chinos (if you insist). A canvas sneaker is acceptable for a more laid-back date, but don’t pull out your old, tattered sneakers. A clean, like-new shoe shows you care and took time to prepare for the date.
KEEP ACCESSORIES TO A MINIMUM
Keep your jewelry to a minimum on first dates; stick to a classic watch or cuff. Simple is better when it comes to first impressions. Their focus should be on you, not your necklace or class ring.
PRESENT YOUR BEST SELF
Finally, here are a few first date dos (though we know you’ve got this):
- Be prompt. Picking them up at 7? Be there at 7. If you’re meeting somewhere, get there 5 minutes early so she will see you when she arrives.
- Have questions ready. This shows you’re interested in getting to know them. Don’t ask them all at once. Let the conversation evolve.
- Put your cell phone away. Keep it out of sight to eliminate the temptation to check it. If you must have your cell phone out, set it face down on the table.
- Have a plan. Don’t pick them up and say “what should we do?” Choose your destination beforehand—then have a couple options ready for later in the evening if all is going well (like after-dinner drinks at a jazz bar or ice cream and a walk).
Above all else, be yourself. Ready to have those go-to date night looks in your wardrobe? Take your style quiz, schedule a Fix and have five curated pieces arrive right to your doorstep. Give everything a try in the comfort of your own home. Keep what you like and send back the rest. Shipping and returns are always free, it’s that simple.
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There’s nothing like scoring a first date with your crush, only to realize—15 minutes before you have to leave—that you have absolutely no idea what to wear.
It may seem that men have it easier than women when it comes to putting together an outfit, and that’s probably true. But there are still some ways guys can screw up and make the wrong first impression. Which is why throwing something on at the last minute before you head out the door could be a big mistake.
So what’s a guy to do? Fear not, for we’ve rounded up the most important style rules, some fashion DOs and DON’Ts, as well as several outfit recommendations to help you get started. Here’s everything to know about what to wear on a first date.
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It’s All About the Fit
What matters most isn’t how much money you spent on your clothes, but how well they fit on your body. The last thing you want is your date to be distracted by your loose and baggy getup. Typically, a fitted (but not skin-tight) silhouette—where your clothes hug but not constrict your body—is the way to go. Look for items like a tailored dinner jacket, straight-leg jeans or slim button-down shirt. It’s all about wearing the clothes versus letting the clothes wear you.
Pay Attention to the Details
Sometimes it’s the smallest things that get noticed, so before you leave the house, make sure every aspect of your look is on point. That means ironing out every last wrinkle crease, brushing away every last piece of lint, and leaving just the right amount of buttons open on your shirt—2-3 max. Not only will your date appreciate how put together you look, but you’ll also feel much more confident yourself.
Consider Where You’re Actually Meeting
Are you grabbing casual drinks at a dive bar, or are you getting dinner somewhere a little more elegant? Dressing for the occasion matters, so plan your outfit based on where you’re going. Your date almost certainly is taking into account the location and what kind of atmosphere it will be, so they’ll expect the same from you. Being on the same page clothes-wise is an important part of the first date experience.
Style DOs and DON’Ts
While every potential suitor has different tastes and preferences when it comes to style, there are certain rules to always keep in mind before stepping out the door.
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YES:
- Always, ALWAYS wear a watch: If there’s one thing you should always wear on a first date, it’s a nice watch. It doesn’t have to be super expensive either — wear one with a metallic strap for a dressy dinner or opt for a sporty version for a casual daytime meet-up. Just having one on makes your whole look feel complete and put together.
- Lean toward dark or neutral colors: Understated, muted colors keep your entire look grounded and sophisticated. Think navy, gray, white and black. It puts the focus on you and your conversation and not on what you’re wearing. This applies to your jeans as well. Dark wash, always. That said, daytime dates are a bit more flexible in terms of color and washes. Feel free to have a little more fun then.
- Wear quality underwear: If your first date ends up moving to the bedroom, you don’t want to be that guy with the flimsy, stretched-out tighty-whities or cartoon boxers. A nice pair of neutral boxer briefs that fits perfectly will never steer you wrong. And even if the clothes never come off, the perfect pair allows you to focus on the date and not on any chafing or wedgies.
- A little spritz of cologne: Smelling good is just as important as dressing right. A simple spray of your favorite scent (one inside your shirt and one outside, near your neck) is all you need to make a subtle impact. No need to go crazy with the cologne. You wouldn’t want the smell to overpower the room.
- Polish your shoes: Please don’t overlook the importance of clean shoes. If you’re wearing dress shoes, a quick black or brown polish is all it takes to make them look brand new. If you chose to wear sneakers, make sure all scuff marks and signs of wear are gone. Jason Markk makes the best shoe cleaning solution to help with that.
NO:
- Hoodies: Leave the hoodies for, well, pretty much everywhere else except the first date. You want your date to know you put effort and thought into your outfit. If for someone reason you’re meeting someone outdoors for a hangout in the cold, opt for a cashmere sweater and denim jacket instead. Layers show intent—hoodies are the opposite.
- Open-toe shoes: No one wants to see your toenails—now matter how well-groomed they are—on a first date. Even if the date is super casual and takes place on a warm day, choose something like a driving loafer or moccasin instead.
- Hats or sunglasses indoors: Don’t let you date think you’re trying to hide something right away. Keeping a hat on might make them think you’re preoccupied with covering up hair loss. Sunglasses give a closed-off impression and wearing them indoors makes you not approachable.
- Ties: First dates should be about making everyone involved feel at ease. Ties can feel a littles stuffy and serious—and that’s why it’s okay to leave them at home. Even if you’re meeting your date somewhere dressy, a simple tailored suit and dress shirt can do wonders.
- Busy Patterns: We’re not saying your outfit has to be boring, but please leave the garish prints and crazy patterns at home. If you’re trying to show off your whimsical and carefree personality through your clothes, start by incorporating smaller bits like a colorful pocket square or printed dress socks. Otherwise, stick with the foolproof neutral colors everywhere and let your humor speak for itself—not through your clothes.
