Nailing the Dress Code

What to wear for every occasion – your guide to nailing the dress code

Dress codes stink. They can be vague and confusing, but we want make them easier to understand. Let’s break this down one level of formality at a time. And ladies, guys need more help, so there’s a little extra information for them. Share it with them. Help me, help them. Let us know in the comments if there’s a specific topic you want covered for the next post!

If you need help deciding if your outfit is acceptable, get in touch and I’ll help you.

White Tie

Guys: The ultimate in formal. Tuxedo required. Ideally, a long black tuxedo jacket with tails, a white pique vest, a white wing-collared shirt and a white bow tie. I’m not spending much time on this because this is extremely rare… like having dinner with the Queen rare. If you’re lucky enough to attend one, call me, as I want to be friends.

Women: A formal ball gown and the option to go as glamorous as you desire with hair, makeup and jewelry.

 Peak lapel tuxedo with a wing collar dress shirt and a white bow tie. Credit:  Emily Gualdoni Wedding Photography

Peak lapel tuxedo with a wing collar dress shirt and a white bow tie.
Credit: Emily Gualdoni Wedding Photography

Black Tie, Black Tie Welcomed or Black Tie Preferred

Guys: This means formal. It also means you should wear a tuxedo. Now this is where you say you don’t own one. Here’s my advice: get one. You will wear it more than once in your life. Personal opinion, go with a peak lapel tuxedo. Shawl lapel is cool, but if you’re an average guy who doesn’t want to venture out, peak is the right choice. Skip the notch lapel tuxedo in general. A blue tuxedo is cool, but if you’re nervous about it, go with black as it will be appropriate in more situations. On the flip side, if you go blue, you can toss that jacket on with a dark pair of jeans and wear it to a holiday or cocktail party. Win.

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My recommendation is to visit Surmesur in the Loop (on LaSalle, between Wacker and Lake) and get measured for a beautiful custom tuxedo that won’t break the bank. Custom doesn’t have to be expensive to get great quality, and Surmesur is a perfect example of that. Another great shop that you’ll regularly find me at is Jojayden in Hyde Park. Wale and his team have beautiful taste and their shop is a blast to be in. Mention the Wedding GPS at both for a discount and perks!

If you’re budget conscious and don’t want to spend more than a couple hundred dollars, check out The Groomsman Suit. They offer stylish tuxedos and suits you can own for less than the cost of a rental. I’m anti-rental and they provide a solution to the terrible tuxedo rental. Pretty cool.

Ideally, you should be wearing a white French cuff shirt. Also, lose the studs. They - more often than not - can make a shirt look outdated and rented (unless you have beautiful/unique studs). I prefer a covered placket, or fly-front, where the buttons are hidden. It’s cleaner and looks quite elegant. 

Wear a bow tie (self-tie preferred!) and a white pocket square that goes straight across. No, you don’t need patent leather (shiny) shoes. Wear a plain black shoe (not cap toe or wingtips) and get them shined before the event. Don’t worry about a cummerbund.

Women: Trickier because you can really wear a formal evening gown of any length… just don’t get carried away. Dressy separates and a formal cocktail dress work too. Ask friends, someone in the wedding party, or someone like me for help.


I should mention that for almost any type of event, even if you have to dress in something that most others will be in (like black tie), you can have fun and show your personality with fun socks! My favorite that I wear most days are from No Cold Feet. Also a local Chicago business, they have great designs and comfortable, affordable socks that will make any outfit more exciting. They also do really cool custom labels for weddings.

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Black Tie Optional or Formal Attire

 Change it up with a blue tuxedo jacket. As a guest at a black tie optional event, a blue tux jacket with matching or black tux pants is awesome. Tuxedo by  Surmesur .

Change it up with a blue tuxedo jacket. As a guest at a black tie optional event, a blue tux jacket with matching or black tux pants is awesome. Tuxedo by Surmesur.

Guys: If you have a tuxedo, wear the tuxedo. If you don’t have one, wear a black or dark suit and a black tie. Black tie optional should mean tuxedo or black suit. If you don’t have either, a charcoal suit will do.

If wearing a tuxedo, wear a bow tie. If wearing a black suit (or charcoal), wear a black or darker straight tie. French cuff shirt ideal for both situations, but a must with the tuxedo.

Black shoes.

Women: Formal evening wear like a floor length dress or a chic evening pant suit.

Cocktail Attire

 Step up your cocktail game by adding a vest. Wearing a bow tie with the suit adds a little playfulness that's perfect for cocktail attire. Outfit by  Surmesur .

Step up your cocktail game by adding a vest. Wearing a bow tie with the suit adds a little playfulness that's perfect for cocktail attire. Outfit by Surmesur.

  A simple blue suit for cocktail attire. Credit:  Oren A Photo

 A simple blue suit for cocktail attire.
Credit: Oren A Photo

Guys: You’ve been waiting for me to say you don’t need to wear a tuxedo. Here it is. You don’t need to wear a tuxedo. A suit and tie is perfect for cocktail attire. Medium to darker blues and greys are great year-round options. Light-colored fabrics are more suited (pun intended) for Spring and Summer months. For Chicago specifically, light grey and blue are most acceptable mid-April until mid-September.

This brings me to a pet peeve. How did that take so long for one to come out? Don’t be the guy to wear the light brown shoe with your dark suit. It’s distracting. And unless you’re wearing a beautiful designer shoe in that color, you don’t want to draw attention there. Wear a medium to dark brown shoe. You can wear black shoes if it’s an evening affair, but if you’re like me and prefer brown or different color shoes, darker is better.

Back to overall outfits…a really cool sports jacket with a pair of trousers and a tie is an acceptable look if it’s dressed up. This isn’t casual, so if you need help deciding, just ask!

Women: Cocktail dress, pant suit or chic jumpsuit.

 

 

Beach Formal

 Linen trousers and dress shirt with a lightweight blazer. Credit:  Oren A Photo

Linen trousers and dress shirt with a lightweight blazer.
Credit: Oren A Photo

Guys: Not many of these events in Chicago, but if you are getting out of the Windy City for a destination wedding, I’m jealous. A summer suit (this typically means both a lighter weight fabric such as a lightweight wool or linen, as well as a lighter, summery color) and a linen shirt with sandals (not Teva’s) is a great look. If you don’t have a linen suit or linen trousers, khakis will do.

Women: A formal sundress with flats. Tea- or knee-length are best.

Semi-formal or Dressy Casual

 This is a perfect, yet elevated, dressy casual outfit by  Surmesur . You will be the best dressed person if you show up looking like this, but in a beautifully not in-your-face manner.

This is a perfect, yet elevated, dressy casual outfit by Surmesur. You will be the best dressed person if you show up looking like this, but in a beautifully not in-your-face manner.

Guys: Between formal and casual… simple right? Eh. Sometimes having all that freedom makes decision time more difficult. Don’t sweat it. Almost any suit and tie or sport coat/blazer and trouser look should do. Feel free to have some personality in your tie or pocket square. Skip the black shoe.

Women: Cocktail dress works perfect here.

Casual or Daytime

 It's the little details in this casual outfit by  Surmesur  that makes it so perfect.

It's the little details in this casual outfit by Surmesur that makes it so perfect.

Guys: Dress appropriately for the season and time of day. That’s the most important piece here. Yes, it says casual. No, this doesn’t mean show up in shorts or 90s jeans. Wear trousers and a button-down shirt or nice polo. Add a bow tie for some fun. Tip: IRON.

Women: Summer dress or a skirt/pants with a nice blouse. Floral prints are great here!

 This is a simple and beautiful casual outfit by  Surmesur , perfect for any daytime or casual dress code.

This is a simple and beautiful casual outfit by Surmesur, perfect for any daytime or casual dress code.

Need help deciding if your outfit is acceptable? Get in touch