Modernize Your Look By Putting a New Spin on the Old. (And don't wear sweats out of the house)

Anonymous writes:
I basically need help to modernize and update the clothes I have. I ideally would like to dress in a modern casual style, so could you give me some suggestions and examples that would fit for my body type? I wear a 36-38 waist, 34 length, shirts are typically XL or Double XL
I'm usually addressing someone who is having a problem dressing and getting a good fit, so it's nice just to talk about fashion in general. At 6'2" and 220, I don't know that I would consider you in the Big & Tall realm, but as an exercise, you might find a proper Big & Tall store and try on some pants and shirts to see if you like how "tall" clothes fit you compared to the clothes you find in regular stores. Clothes with a Tall designation are cut for people 6' and taller so you may discover that Tall pants, which have a longer rise fit you better and that Tall shirts, which tend to have longer sleeves, lower chest pockets, and longer shirt tails for tucking in, more suited to your body type. To your eye, the clothes may not look different but may fit you better when they are on you. Typically, Big & Tall stores will carry garments starting at Medium Tall, so you should find plenty of selection for your build. Be aware however that clothes from these type of stores tend to be more expensive. I do a lot of my shopping at discount stores like Burlington Coat Factory then fill in what I need from retail stores like JC Penneys, then, if I need something specific that I can't find at one of those two places, I head into a Big & Tall. This bottom-up approach saves me money, and I make sure the nice clothes I do have, I take care of by hanging them on hangers right and cleaning things according to the instructions.
If you are wearing Large or XXL garments, you have the option of shopping at regular outlets. Even your 38"-34" pant size is a pretty common size in most retail stock, so I'm going to infer that it's not access to clothes but rather perhaps a willingness to shop that may be what we need to address. Anybody can just put on a pair of Khakis and a dress shirt and look fine for work, but you want to look modern and casual, which means you have a vision for how you'd like to present yourself to the world. That's a great start. The next part is knowing what's out there. Plan a day where you go look at the latest clothing on the rack. The thing to do is ask yourself if you can imagine yourself wearing what you see and if it fits the image you want for yourself, and not allow what the stores are selling to change your vision for your style. There are a lot of people out there, and everyone wants something different, so if something doesn't look right, then walk past it, it's for someone else.
PHOTO 20161005 035441I think part of my own style was built on considering the people I admired in my own life: my uncle, my grandfather, the professionals I work with, celebrities I think are cool and considered how they presented themselves to the world. I don't feel like I'm copying them, just allowing their style to influence me. It's a useful exercise because you reflect on how someone's selections color how you perceive them and at some point, you realize everything you put on is a conscience decision to present yourself in some way. Every piece of clothing you wear communicates something about you, even if you don't intend it to, so take an active role in deciding what you wear. Ironically, sometimes dressing nice is a way to not draw attention to yourself as people tend to notice flaws and sloppy dress. Dressing well is about making sure people pay attention to the man inside the clothes, and not the clothes.
I sometimes put on clothes that are outdated, because they remind me of my grandfather and I'm okay with that. Of course, if today is the day I'm wearing a "grandpa" shirt, I pair with cool shoes or up-to-date jeans, because I'm not him, I'm me. You need to decide on who you are, who and what inspires you, then let that inform your clothing purchases. Figure that out, and take an active interest in shopping and your style will follow.
In the photo you sent me, I see no problems with the basic fit of the clothes you are wearing. However, you are wearing what I consider to be a fine look for hanging out with friends or low key events. I hope I don't need to say that a sports jersey and sweat pants are inappropriate for work, dates, even being out around town. An easy enough maxim is: If you don't like how you've been looking, don't wear what you've been wearing.
I understand that a lot of fashion is regional and even within a particular region, what people thinks looks good varies from social group to social group, so consider my advice then figure out if it makes sense to you in your situation. I know those sweatpants aren't meant to be a finely tailored garment, but when you shop for jeans and slacks, consider the rise in pants and how they fit you in the seat. The crotch shouldn't hang down, and the legs of your pants should not bunch up at the bottom. A rule of thumb is your clothes shouldn't add any bulk or weird shapes to your body. Your pant legs should fall straight down to your shoes with a slight break at the bottom, but if your pants are bunched up, get them hemmed at a dry cleaner. You aren't quite a big guy by "big guy" standards, but you aren't a slight guy either, the clothes you wear should fit you well, and there is no need to wear baggy clothes to look bigger or add any bulk.
If you want to look modern, don't be afraid to try out patterns and colors. Every day, try to put on something you think is interesting. Men's fashion today is much more accepting of flamboyant details and bright colors. Try something out that is orange or purple, or has a funky design. If you prefer a more muted pallet, put on a flashy watch or interesting shoes. 
Here is a challenge for you, after a shopping trip to get whatever you need to pull this off, go four days in a week wearing shirts that button up, and at least two of those shirts should NOT be solid colors. Wear slacks (You need a pair of brown and gray slacks, standard) on two days to a place where you'd usually wear jeans and jeans to a place you'd usually wear sweats. Go all seven days without any sports jerseys or graphic t-shirts. It may be tough, but plan it out, and see how you feel. Also, see if anyone notices. If they do, take note if it's positive or negative feedback. I'll put money on it being positive.
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