It's one thing to have an expensive wardrobe, but if you can't wear the right things at the right time, you've failed before it has even begun.
A meal with the boss
First thing is first, it's important to remain professional, even after hours. That doesn't mean you can't let loose and crack a few jokes with the boss you can get comfortable with. However, it's dinner at a restaurant with the head hancho and you want to look your best. A black suit is always a classic choice for an evening out. But leave the tie and dress shirt at home, you don't want to look like you're entering a room for a Fortune 500 meeting.
A slim-fitted dark suit, better yet something tailored, goes best with a black polo. Short sleeves that is. It strikes the perfect balance between sophistication and fun comfort. A simple, leather wristwatch (two-dial watch) will round the entire look off quite well. As for the shoes, keep it basic with oxford lace-ups or a pair of Derbys. And you can always take the suit jacket off when things get a tad too hot.
Love is in the air
Nervous for that first date? Whoever the lucky lady is, you'll have to dress proper without looking intimidating. The focus should be on her, while your outfit carries plenty of style. This look should reflect your first date - not too much pressure and be at ease. If you look comfortable, she will actually feel comfortable.
Starting from bottom to top, take out those brown penny loafers. Slim-fit khaki or casual trousers should be the next step. Remember, you can't sacrifice too much when it comes to comfort. You can put on a simple striped t-shirt and layer it with a causal, chambray shirt. Even a dark-wash denim jacket can substitute for the shirt. And don't be too shy to roll up those sleeves.
Mom and dad
So you've got the first date, and the many dates after, out of the way. Now, it's time to meet the parents. A dinner with your significant other's biological parents can be more nerve recking than meeting with the president. Fortunately, this is where you get to mix things up for your dinner outfit.
Usually, a classier look can be set by a grey, linen and wool-blend blazer. Unfortunately, we've got our signature suffocating heat to deal with. Some cotton and linen-blend blazers have a different texture, consequently changing the shade of grey. A grey blazer, sky blue dress shirt, a light-brown tie and navy slim-fit trousers is the look to aim for. You can be slightly adventurous with your shoes. Lace-up boots or even classy brogues will do the trick. And of course, make sure they are brown.
A get-together with your closest friends over a fine meal is always a good idea. This is possibly you're favourite time in the week. In turn, you don't ever want to over think it as you have only one goal coming out of your closet. Comfort. Oh, yes, that means your favourite pair of Nike or Adidas sneakers. Mixed in are your slim-fit jeans and your short-sleeve Henley shirt. A casual long sleeve shirt works just as good, but you'll have to tussle with the sleeves a bit.
The key here is to keep it as simple as possible. But we don't have to remind of you that, now do we?
Not every meeting or interview takes place within the confines of an office. Out and about at restaurants or even a posh cafe is a natural replacement. Just because it's outside the office, that doesn't mean you should relax on your approach. In this situation, first impressions might just be everything. And the first impression can definitely be your last, tread carefully.
Don't even think about compromising on your suit. This means no off-the-rack. By now, you should have picked up on the style cues, regardless the season. Get one of your go-to bespoke suits, preferably navy or dark blue, and head out with the intention that you've always deserved that job. No matter the position, a leather zipped envelope bag can take you a long way. Gone are the days of briefcases or looking like an amateur as you fiddle with your CV, leaving all other possessions at home.
This is all about looking professional and carrying on without the world's weight on your back. Proper posture and a confident mood will hand you a more favourable outcome.