Question: "I often end up wearing the same suit styles when it comes to work and weddings. What do I wear to a wedding that's less 9-5 Wall Street?"
When a wedding dress code does not stipulate whether morning dress or black tie is required, it can be a challenge, for the well-dressed anyway, to take a step up from one’s regular work attire of suit, shirt and tie. For an evening affair, I would suggest a lounge suit in a darker colour with a slight sheen - kid mohair blends are worth considering. A darker tie in fine grenadine silk (a jacquard weave with a gauzy effect) or a knit will look suitably non-office like. Select a shirt collar style that you do not normally wear for business, such as a tab, extreme cutaway or long narrow spread.
For daytime ceremonies, opt for a semi-plain mid-tone suit in a subtle texture such as a sharkskin or birdseye (fear not, no animals were harmed in the making of said fabrics: sharkskin is a smooth worsted cloth with a soft two-tone finish typically achieved through a basket-woven process; birdseye cloth is a spot-light micro design in a worsted wool). Peaked lapels look suitable dressy and the addition of a waistcoat ups the formality, particularly if it is double-breasted. A contrasting vest in a light colour is a smart, dandyish touch. Avoid the compulsion to wear a “crisp white” and select a plain coloured shirt in sky blue or cream. Avoid all but the subtlest of stripes or plaids – it’s not your big day after all. A rich woven silk tie in a discrete pattern is better than a sickly pastel satin in a shade best left to the bridesmaids. If you don’t normally wear a pocket square (why the hell not?), now is a great time to start, so pick a suitably festive pattern that contrasts with your tie in both colour, pattern and texture. Highly-polished black shoes are de rigeur.