1. For a man under 30 in a casual work situation (i.e. No need for a suit and tie day to day) and wanting to look stylish what's the best bang for your buck? In a nut shell I'm 26, still in school and working very informally till I graduate. I never know what to buy and how much to spend on anything. Levis 511 / 510 fit great, come in plenty of great washes and cost $60 (or less) but Nudie Jeans fit a little better, come in slightly less washes, and cost upwards of four times the Levis… Is it worth it?
It's the same across that board for anything; shoes, pants, jeans, jackets and I'm not sure what piece is worth the most investment. Should I suck it up and buy the nicer jeans because of the (slightly) better fit? Are shoes a better bet under 30 because of the shoe culture of today? What about a truly top quality jacket? Ugh it's all too much. Help please! – Aaron
You’re trying to focus on too much at once. Brands, fit, price, essentials, etc. Trying to address every issue at once will get you right where you are now—nowhere. Just like a house, your wardrobe should be built form the ground up. A house without a strong foundation will get blown down by the big bad wolf and so will you without quality shoes. Shoes are always a good bet no matter your age. The military will tell you that the most important part of a soldiers body are his feet and keeping them dry and well maintained is essential to survival. It’s the same for a man in the office, in school, or just on the streets.
Unfortunately, many men these days are more focused on brand names, labels, and logos than the actual quality, heritage, and construction of the garments they are putting down a full week’s paycheck for. I always recommend fit over branding. Wear the clothes that fit physically and financially. Wearing a pair of jeans that only fit “slightly” better that cost four times as much as jeans that fit just as well is ludicrous in my book. If you’re still disappointed with the fit find a tailor and he’ll get you the right fit for pennies on the dollar compared to jeans with a triple digit price tag.
The piece that is worth the most investment depends on your position in life, your work and/or school environment, your social life, and ultimately your budget. Every man no matter what his stage in life, where he’s headed in the world or the size of his bank account can benefit from a well fitting navy blazer. It can be dressed up and down, works well in causal and professional environments, and hides stains well. Focus on building your wardrobe one brick at a time and pay more attention to fit than branding and you’ll be ahead of the game.
2. I'm a big fan of dressing formally, from suits to button up shirts with a coat and dress shoes. My problem is I'm only 17 and in high school, all my friends get annoyed that I over dress for the casual things we do, coffee etc. Though the girls love it and I know I look good when I step up to formal attire. Any advice would be appreciated; maybe you were in a similar situation at my age? – George
Well, my friend this doesn’t sound like a problem at all–at least not for you. It seems like the crowd around you are the ones with the problem. There is nothing wrong with dressing well at a young age. However, you do have to be aware of your surroundings and how your presence affects others.
Know that if you’re wearing sport coat and wingtips and your friends are wearing cargo shorts and flip flops that they may feel intimidated by your presence. If you’re OK with this then I say well done. If not, then I suggest toning it down while still keeping your look pulled together. Rather than wing tips try loafers or bucks. Instead of sport coats try cardigans and pull overs. Instead of flannel trousers try chinos and dark wash denim. These options will tone down your look without making your friends feel out of place, and most importantly, keeping you classically cool and stylish.
3. I live in Chicago. I always battle with what to wear for a night out with friends. Jeans, shorts, button-down shirt, polo? How do I get a dressed up look while staying cool? – Raymond
Going out on the town with your buddies, cronies, friends, pals, bros or whatever you call them is a rite of passage for very man, and enjoyable one at that—unless you’re reenacting The Hangover. That being said, a night out on the town is a special occasion and it should be treated as such. Shorts and polos rarely pass muster for a special occasion.
Your best bet to always look good no matter the locale and no matter the agenda for the night is a fitted collared shirt. It can be a pull over or a button up but it must fit. Dark wash denim is always the best bet. Forget the whiskers, distressing, and fraying. Get something in a straight leg and burn your boot cuts. For footwear options slip on some loafers, tie on something in a casual suede, or pick a sneaker in plain navy, white or gray and you’ll be set for most occasions. Staying cool is about wearing outfits that are transitional and can take you from a restaurant to a bar and in between without you being self-conscious. After all you can’t be cool if you’re worried about your clothes.