The Ultimate Guide to Dressing for Success: Building Your Wardrobe, Putting Your Best Foot Forward and Tackling the Day with Confidence

The concept of dressing for success is not new and some could argue it is outdated in todays more “casual” business world. While the old rules aren’t relevant in today’s world, whether right or wrong, how others perceive us and how we perceive ourselves does have an impact on our success. "Suit Trauma" is a very real thing and is often the reason why many men (and women) have expressed disdain at wearing a suit, let alone shopping for one!

We’re going to walk you through why this is important and some basics to get over this fear and start feeling and looking your best. What to look for in fit, staples to build your wardrobe, how to put it all together, casual Friday looks and caring for your clothes. 

Why Dress matters 

The business dress code is changing, there are more options, at times things are more relaxed, but as women have known for years, more options is actually more stressful. Are you making wise decisions that really are setting you up for success? While it’s more laxed, image still matters. We live in a world where you could argue image is actually more prevalent today with all the online channels and the emphasis on personal branding.

It’s naïve to think that only talent, intelligence and hard work is what matters in your career progression. I have personally witnessed it firsthand, individuals who were good at what they did, but couldn’t be trusted to be professionally presented in front of clients or weren’t respected by their peers were overlooked for promotions. The good news is, this is completely in your control. We aren’t telling you to “sell out” we’re telling you to position yourself in the best possible position to shine. As you.

Your appearance and presence is an outward symbol of how you feel about yourself. It starts from the inside and shines out, we attract what we feel and give to the world.  What I’m talking about here is a confidence that starts within and then translates through your presence and commands attention. We want how you feel about yourself and how the world perceives you to be in alignment. This is about helping you be the best YOU, removing your walls and being seen, fully.
The goal is to showcase yourself. In the most flattering way so you feel your best. We want to help you conceal things your self-conscious about, highlight the parts you love and help you visually look taller or 10 lbs lighter- or more muscular, whichever you prefer

The external transformation is real, but it’s the internal one that really just shines through. The confidence that comes with clothes that fit well and then the physical appearance of clothes that fit well make a killer combination. Fit matters, showcase yourself in the best light with something you can control.

fit comparison

Fit: How your suit should fit

Suits can be traumatic for some, most honestly. If you have ever shopped for a suit, I’m sorry, it’s rough for almost everyone. The options are boring, the fit is not usually great and most places are so pushy.  We refer to it as suit trauma and it’s real, you’re not alone. There is a common misconception that only certain body types can’t fit in off the rack, but we are here to challenge that. Yes, there are a few select individuals who can put off the rack on and it look great. But most people have to sacrifice something- and when it comes to fit, you shouldn’t. Even the smallest of changes can make a major difference in the look and feel.

Everyone has their preferences on fit and those can be accommodated, but there are some rules of thumb you need to know to make sure not only you look your best, but that you’re comfortable.  Comfort is just as important, you need to be able to live in these clothes and if they aren’t comfortable, why would you wear them? It also matters in your confidence. The clothes are your armor and should move as part of your body.

fit guide

Download our fit guide to take with you here 

  • Sleeve Length- The sleeve length should not be too short, but short enough that the shirt peaks out at least a ½ inch when wearing with your arms in a normal hanging stance. 
  • Torso Fit- Should be fit/cut into you torso, creating the waist line but not being too tight. This moves away from the hanging, boxy look of a lot of men’s suits. 
  • Shoulders- The seam should hit the edge of your shoulders, not hang over or be too tight. It should be tight enough that it fits well without pulling when standing, but you should not see the gap in the shoulder when you move your arm
  • Pant Length- The pants should touch your shoe, but not bunch when hanging.
  • Pant Leg- The pants should be “slim” but not tight and the seat drop should not hang too low. 
  • Jacket Length- The jacket should hit the base knuckle of your thumb when your arms are hanging by your side. In the back it should be at the start of your butt turning under. 
  • Shirt Sleeve Length: The sleeve should sit about the wrist or slightly past it, not down the hand. 

A quick guide to the best fit is above. For a more in depth look at each of these, check out our blog A Complete Guide to the Perfect Fit Suit 

Building your Wardrobe

Now that you understand the importance of fit, let’s look a how to efficiently build a professional wardrobe. Wardrobes are built in time, adding pieces as you go. The goal here is to highlight some staples for the ability to really extend your options as you build up your inventory.

This is an outline for a small, serviceable wardrobe that will cover the basics for almost any business-oriented career. Once you have a feel for your office’s culture, you can add more of what you need to your wardrobe. Maybe you feel like you need more suits because of the formality of your office, or potentially, you want to wear jackets without a tie and want to branch out to more blazers and jeans on casual Friday. 

2 Suits   x   2 Extra Pants   x   1 Dark Jean  x   5 Shirts   x   5 Ties   x  2 Shoes   =  275 looks

wardrobe builder

Download our wardrobe guide to take with you here 

  • 2 Suits: a light to medium gray and a navy suit are the two colors we recommend starting with. They are incredibly versatile for work or social and can be paired together for more combinations. Solid to subtle patterns on both to extend the versatility.
  • 5 shirts: not to be overlooked, the shirts are extremely important in the fit and colors. Solid shirts are the most versatile, you need at least 1-2 white and 1 light blue shirts because they literally go with everything and are classic. 
  • 5 Ties: The great thing about ties, is that they are an easy and fairly inexpensive way to make your wardrobe feel bigger. Your options are generally open here
    as it’s your personality- but recommended colors that are extremely versatile- Reds, purples, greens, and light blues.
  • 2 shoes: Typically, you need at least 1 brown and 1 black shoe. However, depending on your style you could get away with just one color, if you go with the navy and gray, I would recommend a brown shoe if you are only splurging for one pair. If so, you could use your second pair for some nice, casual Friday shoes. Maybe a nice canvas tennis shoe look.
  • 1 dark Jean: Whether you travel occasionally for work or your office just has a great casual Friday policy, a good pair of jeans is going to come in handy. Go with a slim-fitting (not skinny), dark denim without all the flair of distressed washes, holes, or decoration on the back pockets. Pair it with one of your business shirts or a button-down sport shirt and one of your suit jackets or fun sport coat if you have it.
  • 2 Extra pants: Trousers, slacks, whatever you call them, you’ll need a few extra pairs in your wardrobe. We recommend wool slacks in complementary colors to the suits that you own.  Or branch out to some patterns with these pants, if you went with solid suits, they will pair well with a subtle pattern pant. If you went subtle patterns on your suits, make your extra pants solids.

For a more in-depth look, check out our blog The Young Professional's Cheat Sheet to Building a Professional Wardrobe

Caring for your clothes

You are investing in yourself,  it’s important you take good care of the things you do buy to extend the life of your clothes. You’ll want to dry clean your suits occasionally, but don’t do it excessively, as it can shorten the life of your suit. Wash your jeans sparingly, too, or the color will start to fade. And when you do wash them, do it inside out and always hang dry.

Finally, your shoes, get them buffed and polished a few times a year, whenever they look like they need a little TLC. And don’t forget about getting them re-soled when they start wearing thin or close to the woodwork at the base of the shoe.

Putting it all Together

How to put it all together and still feel like yourself. We run into this all the time and we want to simplify the art of styling.  It doesn’t have to be an art. The main thing is- wear what you like, clothes are to be an expression of you and your personality. All of these are guidelines to help you, but it’s about what image you want to project to the world. We are here to help you be the best YOU. 

We have more in depth guides to styling various colors and combinations, use this color guide when in doubt. You can also chat with one of our stylist about your personal needs. 

color guide

Keep this color cheat sheet with you. Download here 

Blue and Navy Suits

Blue is the most popular color when it comes to suits. There are thousands of men's navy suitvariations of each, but navy still remains the most versatile, classic look available. It gives you a suit that can be worn for weddings, funerals, happy hours, the office, really any occasion to look stylish and classic.  A classic navy suit has replaced the need for the black suit of old. 

Don't think you are stuck to just navy, there are so many shades of blue that are really good options for your wardrobe. Depending on your needs, if you plan to start with 1 or 2 suits, I would recommend a navy or a darker blue. Blue is a great color to add some variety and personality, there are so many shades available for you depending on your need and what you like. Whether with a pattern or lighter color. Here are a few examples of some good blues that would be a nice addition to your wardrobe. 


Now that you're home, you likely don't remember what the salesperson told you to pair with your suit. It's normal and takes time to build that comfort if you're new at this. Use our color guide anytime, it was made for you to simplify the process. It's not the end all be all on colors, but if you use it you won't go wrong. As you grow in comfort feel free to start branching beyond. 
  • Shoes- The most common color worn with blue is brown. Black can be worn with navy, despite some's believes. It is a classic, sophisticated look. The main thing- wear the same color belt as your shoes. 
  • Ties- Really any color goes with blue, again it's beyond versatile. I would avoid generally matching the exact shade blue as your suit. If you have a navy suit I wouldn't go for a navy tie, but don't be afraid to wear blue with a blue suit. Navy- wear lighter shades of blue ties. Other colors to put with blue: red, purple, green, yellow/gold, orange, brown, pastels.  

blue men's suit

Check out our blog to style your navy suit: What to Wear with a Navy Suit (The LBD for men)

Gray Suits

Gray Suits are a close second in popularity and versatility to blue. This is the grey men's suitsecond color I would recommend everyone needs in their wardrobe. If you're own a navy suit (which you should) I would suggest a light to medium shade of gray. Specifically because that shade of gray will pair very well with your navy giving you great mix or match options. 
  • Shoes-  Lighter grays you can wear brown or black, depending on your preference. With your dark, charcoal suits- black would be recommended, but brown can be worn. The main thing- wear the same color belt as your shoes. If you're on a budget and don't wear your suits frequently, invest in 1 blue suit, 1 light to medium gray suit and 1 pair of brown shoes. The shoes will go with both and the jackets and pants will be interchangeable extending your wardrobe. 
  • Ties- Really any color goes with gray as well. I would avoid generally matching the exact shade gray as your suit. Color suggestions for light gray: blues, green, purple, orange, black, pastels, yellow. Color suggestions for darker grays: black, purple, red, lighter blue, orange, green, pastels.

Check out our blog to style your gray suit: What to Wear with a Gray Suit

Brown, Red, Purple and Green Suits

Don't sleep on the brown suit, there are some beauties out there. This is one I would typically suggest you add after you have at least your gray and navy suits covered. 

Another hot trend to pay attention to:  colors in the red, purple and green family. They are growing in popularity as people are rediscovering the joy in wearing suits and having fun with them. Depending on the shade and the industry you're in, these can still be a professional office wear look. If you're in a more conservative office, then I would save these 3 for blazers or for social events. We refer to these as your party suits, pull them out for the wedding and be the life of the dance floor.  

red suit 

Blazers: Mixing and Matching

Too often overlook is the power of a good blazer and pair of jeans.  This is a good men's blazer option for literally anyone- if you work in a buttoned  up office, save this for "casual Fridays". If you work in a more relaxed office setting, make blazers a staple in your wardrobe to still be respected, professional and put together without committing to the full suit. Use this look for happy hours, date nights and other social events to impress.

When deciding on a blazer to add to your wardrobe, the options are close to endless. We suggest adding personality here by picking a colored blazer such as red or green or a louder pattern you love, but wouldn't wear in a full suit. Bold patterns are very common in blazers. When styling a blazer it is wide open depending on the situation you're wearing them. Use your judgment what's appropriate for the environment you're wearing it. 


  • Business look: wear a complementary colored slack with your blazer to the office
  • Casual office look: pair with a pair of chinos, it's a more casual look than the slacks but a step up from the traditional jean.
  • On the town: Pair with a pair of jeans, but make sure they are darker and fitted. Not tight, but do not pair with your "work" jeans.

red blazer


  • Business look: pair with a nice lighter colored button up. similar to what you would wear with a suit. Possibly a tie depending on your office.
  • Casual office look: pair with a pattern shirt that complements the jacket or wear a solid shirt but with no tie
  • On the town: Pair with any of the above or mix in a nice t-shirt or henley. 

Overwhelmed, don't have time or hate shopping? No problem, we'll work with you to determine your needs and curate pieces just for you. Get information on styling services here 

green blazer