What To Wear To A Wedding

By now you probably have a stack of summer events you’ve RSVP’d to, from weddings to engagement parties, so now tough part begins, attempting to understanding that dress code and figuring out what the hell to wear. Unfortunately, we live in an age where dress codes have become more and more confusing and unnecessarily complex. But the good news is, I’m here to help you figure it all out and, more importantly, help you out with what to wear.

To begin unraveling what the hell “Beachy Vacation Casual Chic” or “Game Of Thrones-inspired forest semi-formal” really means, it’s important to think about the event and put it in context with four main types of dress code: black tie, formal, semi-formal, and casual. Once you do that, it’s as simple as can be. Stick to the four following examples and dress accordingly.

The Invite Says: Black Tie

The most formal code for obvious reasons, a black tie dress code means tuxedo only.

What To Wear: A tuxedo

This isn’t the place for a suit so embrace your James Bond moment. There are lots of tuxedo options these days, from navy to grey, but if you’re unsure, stick to the classic: black tux, white shirt, black bow tie, and white pocket square you can’t go wrong and provided everything fits properly, you’re going to look amazing.

The Invite Says: Black Tie Optional

Also Known As: Formal

This is the most common type of dress code for evening weddings and, similarly, formal events. You’ll see some people in tuxes but suits will be most common.

What To Wear: A tuxedo or dark suit

By all means, be the best-dressed man in the room and wear a tuxedo, I encourage it. But, a classic dark-colored suit, like charcoal or midnight navy, works equally well. Keep your shirt choice simple and go with white and keep the color in your tie to a minimum. Ideal combos include a white shirt with a simple black, silver, burgundy, or navy tie. I don’t really recommend a ton of patterns or colors here as it’s not really the place.

The Invite Says: Cocktail Attire, Evening Attire or Something with Formal

Also Known As: Semi-Formal

The most common type of dress code, especially for weddings and events in the afternoon or evening.

What To Wear: A suit or blazer with a tie

Depending on the time of the event (day or night) most suit and tie combinations will leave you looking like a sharp-dressed man. Charcoal, Navy, and patterned suits all work for this dress code. If it’s an afternoon or daytime event and outdoors, you could also wear a lightweight cotton suit or blazer combination, especially if it’s going to be hot. Feel free to add a pop of color or print as a personal touch if you’re feeling adventurous. A tie isn’t mandatory, but I always recommend one for events like this.

The Invite Says: Anything with “Resort”, “Beach”, “Garden Party”

Also Known As: Casual

Sure, it’s the broadest category but also potentially the biggest minefield. The most important consideration here is location and time of day. Daytime and beach events are pretty much an open field but I always say ‘dress to impress”.

What To Wear: Dressy Casual Shirts and Pants

Simple cotton, chambray, or linen shirts, chinos, and cotton dress pants work best. For a stylish touch, I recommend throwing on a silk knit tie. For an event that’s slightly more formal, say summer weddings and engagement parties or an evening event, dress up your chinos and shirt with a lightweight cotton or wool blazer and throw on a pair of loafers. You can also feel comfortable wearing all types of colors and patterns here, provided they’re appropriate for the event.

Don’t forget to check out my favorite picks from The Tie Bar to get you ready for wedding season!

Don’t forget to check out all my picks from the video!

Video Picks

Ties from The Tie Bar

Shirts from The Tie Bar

Now that you’ve got your wedding style game plan set to go, all that’s left is to brush up on a few dance moves.

Pocket Squares

Pocket squares are an essential accessory because when I talk about the smaller details that set the average guy apart from the well-dressed gentleman, this is exactly the type of accessory I’m referring to. It’s an easily forgotten item that adds a little extra polish to an outfit and really sets you apart from the average guy.

If you’re relatively new to pocket squares, the worst thing you can do is go overboard with them. I see it all the time. It’s a very fine line between looking sharp and tacky. Classy and subtle wins out over loud and flamboyant every time. So please don’t complicate your pocket squares any more than necessary.

Before we get into the pocket squares you should own, let me answer some of the common questions I get asked about pocket squares.

When to wear pocket squares

Anytime you’re wearing a jacket, either with a full suit or a blazer or sport coat. You can also wear them with unlined/unstructured blazers like I discussed in my Summer Essentials ebook. But, never, and I mean never, should you wear a pocket square with an overcoat or top coat.

Do I always need to wear one with all my suits and blazers?

No, but I’d suggest wearing one more often than not. To me, the more casual the outfit, the less necessary one becomes. But even then, the quickest way to add a little extra polish to an outfit is with a pocket square.

How Do I Match My Pocket Square to my outfit?

First off – if you’re matching your pocket square to your tie exactly – stop immediately.

It’s a rookie mistake I see a lot of guys making and it looks bad 100% of the time. I just think of all those silk tie and pocket square sets in prom photosshudder.

Matching your pocket square to your outfit is pretty straight forward.

The safest thing you can do, which looks great 100% of the time, is to match your pocket square to your shirt. You will NEVER go wrong there – as long as you’re not wearing some obnoxious dress shirt color like red or orange. Even then, it wouldn’t look… horrible. So do that if you’re going tie-less or wearing a black tie.

Solid tie that isn’t black

Make sure your pocket square is a similar color (not exact) to the color of your tie. Or, if you’re using a white pocket square with colored tipping, make sure the tipping is a similar shade of the same color.

Patterned tie

Find a color in the tie and have your pocket square, either the tipping, pattern, or solid color of your pocket square have a similar color in it. It doesn’t need to match perfectly, but it should have a similar shade of the color as your tie. So if you’re wearing a blue tie, have a blue shade in your pocket square.

Plain tie

Match your pocket square to your dress shirt. It doesn’t need to be perfectly matching, just a similar shade of the same color. That will keep a nice contrast between the items you’re wearing.

Going Tie-less

Again, match your pocket square to your shirt color.

So if you’re wearing a blue suit and white dress shirt, then you can wear a white pocket square.

What Material Should My Pocket Squares Be?

This one is simple: cotton.

Cotton works in 100% of situations, no matter the outfit, color, etc. and goes perfectly with your essential silk ties. So don’t waste your time or complicate things further by even considering other materials.

I occasionally use wool or linen pockets squares with clients or on shoots, but they have very specific use cases and cotton pocket squares would still work in all of these situations, so stick with cotton and you’ll be just fine. For silk pocket squares, I think I can count on one hand how many times I’ve used them over the course of my career.

What Colors and Patterns Should My Pocket Square be?

I’ll always default to classic and timeless colors and patterns so stick with these and they’ll go with any suit or jacket you’ll own:

  • Plain white (if you have 1 color, this is the color)
  • White with gray or navy tipping
  • Navy or gray gingham patterns

Any other types of patterns or colors and you’re venturing into territory that’s outside the scope of this series and where things can go wrong very quickly if you don’t know what you’re doing – and trust me, most guys don’t know what they’re doing in this department, even the so-called “experts”.

I’ll do a whole other video or series about patterns and materials later on, but that’s next level stuff and is not appropriate for the Essential Accessories Series since these are the items that need to work with my Men’s Wardrobe Essentials and also need to work for every guy, regardless of his age or body type.

How to fold a pocket square

Check out my article and video about the 3 best ways to fold a pocket square.

Best Pocket Squares

Honestly, it’s hard to go wrong with any pocket squares, as long as they’re cotton and you’ve stuck to plain white, white with colored tipping and navy or gray gingham patterns. So if you have a preferred place to get your pocket squares go ahead and use them.

I get hit up by a gazillion tie and pocket square companies all day long, but for all my pocket square needs – and they’re not paying me to say this – I use TheTieBar.com.

I’ve been a customer of theirs since they were a little company, who didn’t know who I was or what I did for a living and and they’ve continued to impress me each and every time I order from them. Suffice it to say, they’re amazing. And trust me, I use them A LOT.

The Tie Bar Solid White Cotton Pocket Square
The Tie Bar Solid Pocket Square with Midnight Navy Border
The Tie Bar Solid Pocket Square with Dark Charcoal Border
The Tie Bar Novel Gingham Navy Pocket Square
The Tie Bar Metric Plaid Charcoal Pocket Square

Pocket Squares Outfit Inspiration

The king of all pocket square inspiration photos is my friend Rainier over at TheDressedChest.com, my images below pale in comparison to his, so go check him out, as well.