We recently flew to Chicago to attend the wedding of a friend. I was excited about this trip because I LOVE weddings, adore Chicago, looked forward to catching up with Chicago friends, and was of course thrilled to attend the YLF Saint Patrick’s Day Gathering. The whirlwind trip was even better than I expected because the weather was unseasonably sublime. Warm, sunny and very opposite to the sleet and cold that we left behind in Seattle. 

It was a pleasure to prep the outfits for all three wedding events. There was a rehearsal dinner, the main ceremony and reception the next morning, and a banquet in the evening. I shopped my closet for all three outfits, and you’ll probably recognize most of the items. I kept the palette neutral across all three ensembles adding colour with footwear and clutch in outfits two and three, which you’ll see later this week.

I am often in a modern classic mood when it comes to dressing up for wedding events and I guess that’s because I don’t get bored of classic silhouettes. They are called “the classics” for a reason and that’s really the long and short of it. I also enjoy the juxtaposition of lady-like items with my boyish haircut and straight-ish body type. As long as the items are updated, crisp, and well made, I feel fab in a modern classic vibe. 

I matched a full, printed box-pleated skirt with one of my favourite button down shirts of all time. You saw the skirt at fashion week last month and the white shirt at fashion week last year. Although full skirts are on trend, it’s a retro classic in my book. I buttoned up the shirt right up to the top for part of the evening, allowing the oversized collar and mother of pearl buttons to function as an accessory. I scrunched up the sleeves to draw attention to it’s buttoned cuffs. It’s not everyone’s cup of tea, but I happen to love a strict and dramatic buttoned-up look. Into the evening, I unbuttoned the shirt for a different outfit vibe.

I finished off the look with micro polka dot black hose, a textured pewter clutch, skinny black patent belt and black stacked pumps. No jewelry other than my watch, wedding ring and specs. I chose my oversized black specs to contrast with the whiteness of the shirt. I find solid black high heeled pumps, especially when they are pointy toed, a severe combination for my pale skin and blonde hair. So that’s why I opted for round toes and colour blocked heels. The bamboo heels add a softness to the outfit and bookend my blonde hair. This was Greg’s favourite wedding outfit of the three. 

I have to suppress my desire to wear this white button down shirt more often because I love it so much. When it warms up, I want to wear it twice a week because it works with virtually all my bottoms. But I also want to keep it somewhat “special”, which means practicing the art of self-restraint.