I'm currently in the middle of a "stop looking like shit" transformation. Going to the gym, new haircut, etc. Part of the transformation is also dressing better. Unfortunately, I had absolutely no idea what to do in this regard, but I'm lucky enough to be friends with a men's fashion consultant who does a lot of work for J.Crew and similar companies. Reached out and explained the situation, got some damn good advice. Since there's always questions on askTRP about what to wear, I thought it would be helpful if I summarized his advice here (cleaned up the formatting and such) for you guys.

I'm 27, by the way. Dressing your age is important, so this will apply most to guys 25-35. Adjust as necessary.

My initial questions for him were what advice he had on what to wear to work (business casual), and what to wear when out socially. Here's what he had to say:

Before answering those specific points, let me say that the most important thing is the fit. If it doesn't fit, don't wear it. It will look like crap and you'll look like a slob. You're a tall, slimmer guy, so it shouldn't be much of a problem. You'll need to purchase/wear slim fitting clothes. Notice I didn't say skinny -- slim means well-fitted and neat. So the fit is the most important thing. Sometimes this will mean you need to go to a tailor.

  1. As a base, you need 3 pairs of non-pleated chinos: khaki, navy blue, gray. These will match with anything, and will always work for business casual. Bonobos is a good move here.

-3 Oxford shirts: white, light blue, banker stripe. Bonobos, Gap, JCrew -Shoes: brown loafers or brown brogues. Nordstrom Rack and nowhere else -Brown belt that matches your shoes in color/tone -Vneck sweaters: navy blue, light gray. Wear these over the oxford shirts to add a layer.

This alone is sufficient for business casual -- will take you to the office and to drinks after.

Also get a solid watch. Target has a GREAT timex watch with a brown strap for 35 dollars. That's my watch.

Regarding socially, you need a fitted pair of dark denim. Jcrew or Bonobos. They must fit right. And you can wear these with anything and everything: casual shoes, t-shirt, dressed up shirt and a blazer. Denim will take you everywhere you need to go, but, it must be: -dark -fitted

Grooming:

This is essential. If you don't have good grooming habits, everything I just mentioned above doesn't matter.

Get into a morning routine: face wash > toner > eye cream > good moisturizer. Exfoliate once a week and no more. Khiels is your best bet. Expensive, but very effective.

Get a solid cologne. Not a chemically trendy one. Find one that works for you and something you can pull off. Something unique. Check out DS and Durga.

At this point, I asked him to elaborate on "fit" and what exactly needed to be tailored. I take my suits to the tailor, but had never considered having a tailor do chinos/khakis, or having them take out all the puffy extra on my buttonups (I'm 6'3" and if a short is long enough on the torso, it's always got way too much fabric around the abdomen, leading to a 'parachute' effect when tucked in). He advised:

Yeah, a tailor can basically alter anything. Bonobos is the best brand for reducing tailoring costs and finding an appropriate fit.

Generally, the less unused fabric the better. For example, parachuted shirt when you tuck it in is no good. Length of pants shouldn't bunch up a lot at the bottom. Waist should fit appropriately -- the less baggy the better.

Tailoring is the solution. But you can just as easily find a brand that fits you right. For example, Jcrew shirts fit me terribly. Gap shirts fit me much better. Bonobos fits me the best. So I buy bonobos. When you find something that fits, buy multiples of that item.

Hope you guys find this helpful, let me know if you have any questions/clarifications/further advice.