Dressing Like A Leader: Style Tips For Women In The Spotlight

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The first date is often a nerve-wracking experience, and for a good reason; what if the person you are sharing your time with on a date becomes the person you spend all your time with, forever? That setup puts a lot of pressure on making the first date memorable, for all the right reasons. After all, it could be the story you end up telling over again with each new friend you meet as a couple down the road.

There are many reasons you should care about how you dress on a first date, and some, while obvious, ring truer than ever. Dressing well sets the right tone because it demonstrates your respect for your date and lets them know you are invested in their time. If this is the first date after a divorce or break-up, remember, you deserve a chance to rewrite your own history.

Choosing the right outfit will give you the confidence to walk into the date with the right attitude and behaviors. When we wear a suit, for example, we’re not merely choosing to wear a two-piece; no, we’re choosing to put our best selves forward and say, “We deserve to be happy.” We walk taller and generally set out to show the world we are a sophisticated man of value.

What you might not know, however, is that choosing the right outfit can also play up your best features, and make your date that much more attracted to you. The first date is a time when you are sizing each other up as potential suitors, and anything you can do to gain the advantage is going to make sure you get the results you want — like a second date!

If the thought of picking something to wear makes you nervous, it’s time to take a deep breath and remember that while clothing is a fantastic accessory you can use to show off, it should also be about feeling comfortable and presenting your best and most authentic self.

Today, I’ll be talking you through a few simple style rules for most first date suggestions to help you set the right tone.

What Not To Wear On A First Date

Now, before we get started, I do want to cover a few quick tips on what not to wear on a first date, because even the best men make mistakes. This could be a topic for its own article, but for the sake of brevity, and in the name of common sense, I’m only going to cover some ground rules. These style staples can stop you from ruining an otherwise excellent date night outfit, and are often overlooked.

  • Not grooming correctly: Why go to all that effort to create an excellent outfit if you haven’t covered all the bases? Check out these grooming tips for single men to find out what women want in their date. You’ll be amazed at the results!

  • Cologne: Again, this could be an entire article, but no cologne is a happy mistake. Too much cologne is a problem. Apply cologne an hour before you leave the house, and only use a small amount. You don’t want to overdo it.

  • Wearing too much: Seconding this point, less is always more; that goes for your jewelry, accessories, and even your tan. Too much sends a desperate “try-hard” signal, and won’t give off the same cool air of sophistication that a more minimal choice can.

  • Being under dressed: While many guys fear the embarrassment of turning up to a date overdressed, I promise that your date will appreciate the oversight. What won’t be appreciated is if you turn up and haven’t put in the effort to groom yourself or dress appropriately (no open-toe shoes, please).

  • Reusing an outfit: If you’re meeting for drinks after work, and sport the same suit, or you always start your date night conversation with, “This is my lucky date night outfit,” I can bet you won’t get a second date. By all means, go with what works, but make sure you are wearing your outfit off the rack.

Now that we’ve gotten the mistakes of what not to wear on a first date out of the way, it’s time to tune into what your date wants!

What Color Outfits Are Most Attractive?


The next point I want you to think about is color, and the impact this has on our phycology. All around us, color plays a pivotal role in how we think, feel, shop, and even eat. In restaurants, red is often used to grab your attention and invoke a primal desire; one that can often be satisfied by gorging on delicious food. Orange and yellow also make us hungry — which is why so many fast food joints use them.

In the romantic world, colors also signify compatibility. You may be familiar with peacocks; the males use brightly colored plumes to attract and seduce their female companions. Scientists confirmed that our perceived chemistry and attraction is often linked inextricably to what color outfits we wear. And it should come as no surprise that red is the top of the lover's list.

What is most interesting about red, however, is that it has a unique effect on men and women. Red indicates passion and desire, in women, but worn on men, it invokes status, power, and virility. This is why you will see kings and other political leaders wearing red robes and suits; in ancient Rome, leaders were called coccinati, meaning “wearing red.”

So, if you want to pick a date night outfit that will hold their attention, and make you feel seductive and powerful, then red is an obvious choice. You don’t have to dress head-to-toe in red, either, to make an impression, a red accent or accessory goes a long way. And fellas, watch out for the “lady in red” — if she is wearing this color, it may mean she wants you to see her — and only her.

Here are some solid choices for colors to wear on a first date:

  • Dark Grey: Black is tempting to wear thanks to its flexibility, but often looks too stuffy and formal; dark grey, however, offers a chic and complementary option in its place.

  • Navy: If you want a sharp look that cuts the mold, navy is the year-round color of choice for dapper men. Navy pairs with almost any other color exquisitely.

  • Pastel: Something is refreshing and wholesome about pastel blue or pink, and is an ideal summer color palette that is fresh.

  • Patterns: Don’t be scared to try out different polka dots, which are classic yet always look clean.

Once you pick your poison, it’s time to consider how to dress for the right season, and how to tailor your date night outfit for any time of the year!

Dressing For The Right Season


Fashion varies with the seasons, out of necessity. In winter, expect to see lots of thicker fabrics, layers, and warmth of color. In spring, expect to see much brighter, fresher colors and lighter fabrics. Depending on where you live, this fluctuation can vary, but as a rule, you will want to switch out your outfits throughout the year to match the weather and seasons.

If the weatherman is forecasting rain, be sure to adapt your outerwear to suit and pick out a waterproof duffle jacket; or if you know it will be hot, look to cooler fabrics such as cotton or linen. It’s amazing how much an outfit can be changed with a quick addition, such as a straw hat in summer, or a woolen scarf in winter. Play around with accessories to get into the seasonal groove.

Here is a quick rundown of what to expect in each season:

  • Winter: With cooler climates and the potential for snow and ice, layers and warm fabrics are your best bet. Layer undershirts, shirts, sweaters, or jackets for seamless outfits that have lots of dimension and style. Accessories include leather gloves and woolen scarves.

  • Spring: The air is crisp but refreshing; here, layers will continue to be your friend, but switch out heavy wools or tweed in favor of cotton and linen. Dark demin works well all year round but is offset with pastel shirts or nautical jackets nicely.

  • Summer: Bright colors and short sleeve shirts signal summer. Pair Capri pants, edgy sunglasses, and slicked back hair for summer vibes. Floral prints and patterns are also a fun way to play up the playfulness that summer brings.

  • Fall: In fall, revert to long-sleeved shirts and pants, but have a good time with boots and leather jackets. Layers will keep off the chill, and look best in autumn colors such as brown, red, yellows, and in textured fabrics, like this suede bomber jacket.

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Now that you have the groundwork covered for what to wear year-round, it’s time to get into specifics of what to wear on your date.

First Date Outfit Ideas


In the following sections, I’m going to breakdown the expectations of what to wear; check out these first date ideas for more inspiration! Before we get started, I want to remind you that while looking good is a key aspect of the first date outfit, you should aim to feel confident and comfortable in what you wear; a man can dress in a thousand-dollar suit and still look cheap if he isn’t feeling it.

Being prepared means trying on an outfit, in its entirety, before the big night to make sure you get a feel for what you are wearing, and to give yourself time to make any changes ahead of the big event. For guys who are dating regularly, having a foundational outfit that allows you to switch up a few items (such as a new shirt or a different pair of shoes) is always a great idea.

The Casual Date

The casual date refers to a relaxed date activity, not a sloppy outfit. The casual date often takes place in the great outdoors and might include a picnic at the park, or a walk on the beach. While relaxed, this is not the time to show her what your day-off attire looks like; instead, look for dressier versions of comfy weekend clothing, such as indigo washed jeans, and dress them up.

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Darker jeans give a nice, pulled-together look that is both casual yet date-appropriate, and can be worn with a short-sleeved shirt (preferably tucked in) for a look that is not too formal, but also shows you know what you are doing. Switch sneakers for leather kicks to take this look from drinks with the guys to the appearance of a casual dating champ.

The Coffee Date

The coffee date is like the casual date but is one of the few exceptions where your date might also tie-in with other events in your schedule, and not necessarily with the person you are dating. This is also the date you might pick if you are meeting someone off Tinder for the first time and want to see if they check out to what they’ve shown you online. Tip: skip the coffee if you know your date well!

For this date, I like to deploy my favorite outfit that I know gets compliments. Again, this is the exception to the rule; the coffee date is only a 30- to 45-minute meet-and-greet, so there’s no overbearing need to turn up looking extra dapper — unless, of course, you want to. Pay close attention to your wallet, watch or backpack to make sure your outfit works seamlessly together; it’s all in the details.

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The Dinner Date

When going on a dinner date, you should always wear a jacket. Depending on the restaurant, the price-point will offer insight into what kind of jacket is appropriate. If you’re going all-in, then you’ll want to keep reading for my formal date attire tips. For most restaurants, however, a chic blazer for men or a repurposed suit jacket are more than sufficient when paired with dark denim or tan pants.

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If you are going out to lunch, you can sometimes get away with a tailored sports jacket, but in most cases, you will want to invite your date out for an evening meal to set the right tone. An easy way to let your date know what to wear is to invite them to an event for dinner, and use that event to gauge the right attire; for example, dinner and movies will be less dressy than dinner and opera.

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Keep my simple style rule of wearing a jacket in mind, as we venture into a few scenarios. These will round-off your outfit perfectly every time.

To The Movies

When going to the movies, a leather jacket is a solid choice. You can wear a black leather jacket with jeans and a tee-shirt for a timeless look, or a brown-leather jacket with casual pants for a hip look. As you arrive at your seats, you can take your coat off. Choosing a jacket that is not too tightly fitted or tight means a comfortable transition from standing to sitting.

While you might think that the movies are a great opportunity to sit in the dark, remember that your date will still be paying attention to you in the lobby, and so on. Your jacket is an excellent way to make a style statement, as you will likely be face-to-face or sitting side-by-side. Avoid the temptation to wear a hat with a great jacket as this can complicate an outfit.

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For Drinks

Much like the cinema, you can wear a casual outfit when going out for drinks. When standing at a bar, I like to wear a pair of leather loafers that accent my outfit, without making me feel like an overdressed penguin. You’d be amazed at how many people will comment on a good-looking pair of shoes while you wait.

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If you are going to a sophisticated wine bar, for example, you can afford to dress your outfit up with a nice watch or a bracelet (not both). If you’re just hanging out at your local bar, this is a rare opportunity to wear a sports jacket. The outfit is largely going to depend on the kind of bar you’re going to, so don’t forget to go check it out ahead of the date if this is your first time going.

The Formal Date

The formal date is all about the fit; just as any formal occasion has clear rules and expectations, you are going to want to pull out all the stops and create an outfit custom to you. The formal date is a time to shine and can start at the classic two-piece suit, through to a full-on tuxedo. For a black-tie or formal event, do not expect to go without a visit to your tailor.

Even a simple suit-and-tie event can be red-carpet-worthy if the cut is correct and built for you. The formal date is a time for black, shiny brogues, and everything to be buttoned up, tucked in, and dust guarded to within an inch of its life. In return, you can expect to make the greatest returns on your investment, as most dates comment that this is the look they are attracted to the most.

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Where To Source Date-Night Outfits


Thanks to dating apps and websites, more people are dating now than ever before. Dating is no longer something we do on a Friday night; dates happen during the weekday, at lunchtime, over breakfast and on the way to another event. That means you need to bumper your closet to accommodate all of these situations and to create new outfits from their ashes. I’m including a few simple tips you can use below to always make sure you have an appropriate date night outfit on-hand, and to breakaway from another trip to the mall:

  • Subscription services: Pizza isn’t the only thing you can order to your door. Mail order services, like Trunk Club, can provide tailored solutions on a one-time or on-going subscription basis. I’ve seen everything from trendy boutiques to formal vendors offering mail order items.

  • Thrifting is in: Where people once shunned wearing second-hand clothing, thrift stores have made a revival under the newer, chicer “vintage” apparel label. Go to second hand shops for a cool accent piece at a discounted price.

  • Your own closet: You’d be amazed at how many times I hear guys say, “I’ve got nothing to wear,” and they have a closet full of clothing. Try on different shirt and pant combos, or switch out a pair of shoes to see how a quick swap can change an entire outfit.

Finally, there are certain things that never go out of style, and these include: being respectful, showing good manners, being chivalrous, and ensuring your date has an excellent time. Put their needs ahead of your own and be attentive, listen to what they have to say, ask questions, and generally set an example for what a great man you are, and I bet you will make a fantastic first impression.


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