Big Men's Fashion Advice: Paul Goes to Disneyland

Deann reached out to me on Fiverr. Her husband Paul is taking a trip to Disneyland with the grandkids soon and wanted some tips on good travel pants.  She also wanted to know how to get a good fit in the seat for a guy who doesn't have much of a rear-end. She is considering a tailor. She included two pics of  Paul for a critique.
Hi Deann,
I hope the trip to Disneyland is fun. Certainly being able to get items tailored solves many problems, especially if you develop a rapport with one who does a good job. Ideally, you'll be able to buy pants off the rack to save money and also know that you can drop by a store anywhere and find brands you know fit well. Knowing you can drop into a chain retail store and grab a backup pair of pants wherever you are at can reduce stress traveling or else one spilt cup of coffee can wreck your whole trip.
In the case of a guy like Paul who is a bit bigger on top but does not need "relaxed" or "husky" pants, look for slim fit or straight leg pants, not to be confused with skinny jeans. Slim pants are an overall cut and proportion, so you should be able to find them in large sizes. 44/32 is a pretty common size even in traditional department stores. Obviously, there are going to be variations from brand to brand, so if you know of a particular pair of pants that look great on him, take note of the brand and always go back.
For travel pants in that size, take a look at Duluth Trading Company's Dry On The Fly Pants. These are a lightweight nylon/spandex pant cut to look like casual khakis. You can wash them in the sink and hang them to dry. They are wrinkle resistant, so putting them on a hanger overnight is all the care they need to look great the next day. There are lots of companies who produce pants like this at various price points, but at $80, they are akin to a nice pair of slacks; I've seen others come in at $120 a pair. If you are only interested in function and aren't concerned with being dressed up, take a look at what some call tech pants. These are lightweight, easy-dry pants you can find at any outdoor or sporting goods store. They are rugged, comfortable, and usually, have zip-off legs so you can convert them to shorts. These run about $50 a pair and are ubiquitous among travelers.
Paul in leisureLeisure Look
Let me start by saying if this is Paul just hanging around the house, who am I to critique how a man looks when he's just trying to be comfy, eh? I'll offer some general observations about things I'd point out if he heads out the door in this. First, considering this is a leisure look, it fits fine, so no problems there. Given that Paul has a light complexion and some salt and pepper in his hair, I'd stay away from solid white on top. Think of his skin tone and hair as the outfit he's got to wear all the time, and it's a color he's got no choice about so he should match and contrast with the rest of his clothes in much the same way he'd pick out a tie. Leisurewear comes in lots of colors and patterns and even if he's just hanging out or taking a quick trip to the store, he's going to run into people he knows and can still look great. I would stay away from stark 50/50 contrasts like a white top and black pants. A lighter pant or a darker top, or items that are a bit more complimentary, colorwise, would make the outfit a bit more cohesive. A style I can't wait to try out are pants that look like regular dress slacks but are made of French Terry AKA sweat pant material. They sound like heaven. Perhaps surprise him with a pair for his birthday and see how he likes them. Finally, it's irrelevant if this an around-the-house look, but in general, dark pants, dark socks.
Paul in suit1Dress Look
That's a sharp looking suit! The jacket fits great, and I can tell the shoulders and collar are right for him. Lots of off-the-rack suits tend to need some help in this department, so that's always the first thing I look at. I'd ask a tailor to re-do the bottom of the slacks; the hem is a tad slouchy. They will look better if that crease down the front of his slacks drops straight down to the top of his shoes without much deviation. If you are thinking about another suit, go gray or navy. Black suits can look great, but these days, it typically means all business and no pleasure. In this instance, a white shirt would be a smart choice. It would make that suit pop especially if you've got a bright tie. I can tell from looking closely that the shirt sleeves and coat sleeves are cut right, but a white or another bright shirt under the black coat would make the ends of his sleeves stand out more and add to the overall look. The beige shirt here might wash out Paul's complexion in certain lighting. Make sure that your shirt and tie choice will stand its ground when paired with an all-black suit. Shoes with a squared toe might dress up his feet; try on a few styles to see if you two can find a pair that appeals to you both. They might not be as comfortable as the shoes in this pic, but I sometimes go with less sensible shoe and put Dr. Scholl's arch supports in them so I can walk in them for longer than an hour.
Would you like your very own personalized fashion advice like this? Hit me up on Fiverr.
Note: I am not a paid spokesperson for Duluth Trading Company, R.E.I., or any Big & Tall clothing manufacturer, but I'm open to it.