The key to dressing good on a first date is confidence. This goes way beyond the outfit you’re wearing. Think about how you’ll present yourself overall. Are you well groomed? Is your outfit properly maintained? Does it fit well? These are questions you should ask yourself when getting ready for a first date.

Why dress well for a first date

When you look good you feel good. Feeling good builds confidence. The focus here is how to properly present yourself to a potential partner.

  1. Dressing sharp shows that you are interested. It shows respect. It shows that you put a lot of time and effort into getting ready; after all you took your time to look your best.         
  2. Being well dressed puts you in a good state of mind. When you look your best, you are confident. A good outfit and fresh haircut helps you focus on the task that is at hand.
  3. Physical attraction matters. People in general are attracted to people who are well dressed. Many women care about appearances and are drawn to healthy, distinguished, well dressed men. Clothing covers almost all of your body, so when worn correctly it can help you look better by showcasing your best features and minimizing your least favourite ones. Be prepared, find the clothing that fits you best.


Dressing for your body type 

The first step to dressing well is to own who you are. Dress for the ‘you’ right now, meaning dress for the structure and size that you are currently.

Here are some tips on how to work with what you have, and some clothing options that will help with common problem areas. Here’s how you can showcase some of your best features:

Defining your shoulders

A sport coat is a great way to give some definition to your shoulders and mid section. A well fitting sport coat will give the appearance of broad shoulders, while making the waistline and abdomen appear more narrow and shaped. 

Do: Get measured by an expert. Choose a fitted sport coat in a neutral tone. Make sure the sleeves are the right length, showing a bit of shirt cuff.

Don’t: Choose a sport coat with sleeves that are too long. Long sleeves will make the coat appear that its too big for you. It’s the first clue that it doesn’t fit. Don’t worry sleeves can be easily tailored.

Accentuate your jaw line 

A fitted dress shirt accentuates the jawline. It will keep her eyes looking above your chest. It draws attention to the collar of the shirt, so you’ll want to make sure that it is fitting properly. Choose a shirt that is a quality fabric to avoid being overheated. 

Do: Go for a shirt that is 100% cotton to reduce perspiration and overheating, during that first date.

Don’t: Choose a shirt that is polyester. This is a fabric known to wrinkle and is non-breathable.

Addressing The Midsection 

A lot of men are self conscious about their abdominal area. If you have concerns about your midsection, layering up is a great way to ‘hide’ this area. A light weight sweater, or vest, will help with this. The middle layer helps cover the waist line, creating a better flow to your outfit. Since it covers the belt, the eyes will not be drawn to focus on that area. Also, you don’t have to worry about finding a matching belt. 

Merino wool sweaters are perfect for layering

Common Pant Issues 

Many men out there run into pant issues. ‘Hockey Butt’, & ‘Chicken Legs’ are common terms we hear a lot when it comes to fit issues with pants. Always consult with a professional to ensure a proper fit for your body. There are times when this won’t be possible. Solution: Choose a performance fabric that has built in stretch. This fabric is now available in denim and dress slacks. Experiment with different fits and sizes until you find a pair that fits you well. 

Do: choose pants that are fitted and have subtle texture. Go for something that contrasts with your shirt and sport coat. 

Don’t: choose pants that are baggy or too tight. Remember, fitted does not mean tight. If your pockets are pulling open, go up a size. 

Now that we have talked about the most common outfit issues and have addressed some of the major Do’s & Don’ts, it’s time to talk about outfit options for 3 different types of dates.

Outfits for 3 Types of Dates

The Dinner Date

This is the most common type of date. This date is where you’ll really want to impress. It’s perfectly fine to go all out with your outfit here, first impressions are everything so make it count.

A Sport Coat can make a great first impression

The outfit: A polished casual outfit will work best in this scenario, think business casual but more playful. Start with a dark wash denim or fitted chino. Layer it up with a merino wool sweater over a patterned sport shirt. If you want to go that extra mile, top it off with a textured sport coat. If it’s a cold evening in Halifax, you’ll want to put on a wool pea-coat with a complimenting scarf. Don’t forget the shoes! Choose one that is right for the occasion, like a cognac wingtip, or a stylish dress sneaker for a more sporty look. A classic brown Oxford with a matching belt would be a good starting point.

The Casual Date 

Casual dates may be more laid back but it’s important to still look your best, while not overdoing it. You can still wear a comfortable outfit, just make sure it’s not sloppy. Try to avoid basic clothing that makes it look like there was no effort put in. Avoid loose fitting clothes like sweat pants or basic blue jeans. Here are some outfit options for the causal Halifax date like a walk though the Public Gardens or an evening of mini-putt at Putting Edge. 

Well fitting jeans are essential to building a good outfit

The Outfit: Fitted chinos, or designer denim topped with a Henley shirt or crew neck T-shirt. A fitted pima cotton polo shirt is another great option. For your shoes, choose a single colour canvas sneaker, suede Chukka or casual loafer. Take this outfit to the next level by adding a half-lined, or soft knit sport coat on top. For the warmer months, swap your jeans for well fitting, solid colour, khaki shorts. When wearing shorts, you’ll want the shorts to sit at the knee or slightly above. No short shorts please. 

Henley shirts are great for layering and look great with denim

The Active Date

For some men, active dates can be intimidating and hard to dress for. You want to be confident and look good, but be relaxed and comfortable at the same time. For active dates such as a hike through Cape Split, Axe Throwing or shooting pool you’ll want to wear something that is comfortable but well taken care of. 

The Outfit: Fitted joggers with a solid colour v-neck t-shirt. Layer with a button down shirt and roll up the sleeves. The layered shirt gives some versatility and you can simply lose it, if it gets too hot. Or, go for a pair of slim-fit tech pants with a contrasting hoodie, layered over a Henley shirt; roll up your sleeves and show off a nice watch. The idea is to create a playful causal outfit that is well coordinated. 

Your shoe selection is crucial on an active date. Don’t choose a dress shoe, it just won’t fit the occasion and will not stand up to any sort of lengthy activity. Choose a good pair of casual Chelsea boots or Chukkas. In warmer weather go for a loafer or canvas sneaker. If you are hiking or walking for long periods, choose a shoe with a durable solid bottom. 

‘Achiever’ Chukka Boots From Alter Sole

Choosing the right shoes

No matter how casual the date is, always pay attention to your shoes. This is one of the first things that a woman will look at. Whether you are wearing canvas sneakers for a walk around Halifax’s Boardwalk, or loafers for your dinner at The Bicycle Thief, you can bet she’ll look to see what you’re wearing. Shoes say a lot about you and are a way to showcase your personality. You’ll want to ensure they are clean, stylish, laced properly and are functional. 

‘Trendsetter’ Dress Sneakers From Alter Sole.

Do: Wear a stylish dress pair of dress sneakers or a pair of Chukka Boots. 

Don’t: Unless you will be hiking or rock climbing, don’t show up wearing gym sneakers or a pair of runners. 

Remember, choose a shoe that says remember me. To hear about some other great shoe options checkout my blog on the modern loafer here.

Suede Loafers From Don Nino

Accessories matter 

Don’t skip on the accessories. This is what makes the outfit unique and is an easy way to showcase some personality. Accessories that you should be thinking about are: a watch, socks, pocket square, bracelets and lapel pins. A good watch is a must have accessory for any man’s wardrobe. It often becomes a focal point of your outfit and is a great conversation starter.

Don’t forget to style your outfit

After you have selected the clothing to make up your outfit, styling the outfit is the final step. This is where you will add some detail and extra maintenance to what you’re wearing. Make sure that your clothing is lint and dander free. You can have the best outfit, but if it doesn’t display well, it can make or break the success of your date. Take the time to tuck your shirt in. Roll up your sleeves, show some cuff, lace up your shoes, undo your top button, fold your pocket square. These are fine details that help make a great outfit. 

Now, you have the basic skillset to get started on your date outfits. If you need help with date outfits, or need more ideas, visit my services section here. Feel free to send me an email with any questions you may have.

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