Guys are a little easier to shop for than girls are, only because casual clothes are more acceptable in formal situations. Also, a lot of formal clothes can be mixed with casual pieces in order to make great cocktail party attire. While a guys wardrobe might be more casual, they are not cheaper. Unfortunately, with how tailored menswear is, cheap options really stand out. The good thing is if you buy non trendy pieces you won't have to change your wardrobe for about ten years. Cuts for suits and breaks in hem lines will change, but if you buy classic cuts you will be safe for years (unless eighties baggy box cuts come back and hopefully they never will!) I think if you are under forty a longer hem line and bigger break is appropriate, the older you get the smaller the break should be. If you don't know what I am talking about, your tailor will, so let them know. That is also a very important tip, all men should have a tailor. Make sure it's one that you trust, who does good, fast work and doesn't overcharge. When a cut is outdated or you fluctuate in weight, go there first before you buy new clothes. They may be able to reshape the piece or take it in and it will be more affordable than buying a new piece.
I am going to go out on a limb and say guys need two different types of jeans, which are a great staple and can be dressed up or down for basically any occasion.
1. Dark Wash Straight Leg or Slim Cut Jeans
This is perfect when paired with a crisp white button up shirt, a nice belt and a blazer. It can be worn to a lunch, casual business meeting, nice dinner or cocktail party. It is very important that the wash on the denim be dark though. Also, the jeans should be hemmed with a medium break so that the back hits a few centimeters up from the ground, this way it looks more like a tailored pair of pants. There shouldn't be too much adornment or embellishment on the pockets (no True Religion) or decorative torn knees. Think crisp and clean.
2. Lighter Wash Casual "Weekend Jeans" (can be any cut that is comfortable)
This is more of a day look. It can also be worn dressed up with a blazer, but maybe instead of a button up pair it with a nice clean tee. No graphic tees, it will make you look like a teenager. Instead, just get really nice cotton tees in solid colors. No crazy embellishments because it just ends up looking effeminate.
If you are like the guys I know and hate jean shopping and just wish you could find one pair you love and have them for the rest of your life then Stronghold are the jeans for you. Stonghold offers off-the-rack denim for $285, as well as made-to-measure trousers which start at $485. The company develops a pattern specifically fit to your body and allows you to choose all of the components (fabric, hardware etc.) that go into your jeans. All Stronghold garments come with lifetime alterations and repairs free of charge, so although you may pass out at the price, they are lifetime garunteed - so basically if you gain weight or rip them (which probably wont happen because it is really heavy duty denim) they replace or fix it. Obviously, this isn't for everyone but if you can afford it and you hate to shop then this is your company. And when paying think of all the jeans you would pay for in the next decade if you bought a cheaper pair, it actually works out to be quite a savings.
3. 3 Solid Color Cotton Tees
Black, gray and one color - this can be worn with basically anything. Remember, the more basic it is the more situations it will be appropriate for. However, when I say basic I do not mean cheap, always buy nice quality - it will pay off I promise!
When shopping I like to try and find organic green materials that aren't hurting our environment too much. Also, it is an investment in our future; shopping is like voting, when you buy something you are saying "I support this." So always make sure you agree with the practices of the company you buy. As the old saying goes, "buyer beware," always be an informed customer. I like the tees from Alternative Apparel, no it is not American apparel, it actually runs a little cheaper and is made with organic cotton.
4. Black Blazer
This is great with either a pair of jeans or a nice black pair of slacks and it is definitely a must have. Just make sure it is really tailored to your body, if you can't find one that fits perfectly buy the closest fit on the big side and then go to a tailor and have him fit it for you. They run expensive so make sure you get what you want.
Theory 'Xylo P. Edison' Two Button Blazer is a great timeless classic cut that is nice quality and still afordable, however if you can spare a few more dollars Acne has amazing menswear, like the Wall Street Mohair Jacket, that really will impress.
5. Black Slacks
Even if you can wear casual clothes to your job, these are important. Black slacks are the perfect article of clothing for weddings, funerals, business meetings, etc.. Basically, any time you have to dress up you can put these on with a button up and tie. If you don't want to be too formal skip the blazer and sometimes even the tie.
6. 5 Nice Button Up Shirts
Styles vary, but I have always been a fan of the french cuff. Is it formal? Yes, but I think it really makes the outfit. Style is in the details!! Make at least 3 of these shirts white, another blue, another (if you are daring) pink, which I think looks amazing on most guys who have the balls to pull it off, and then another in whatever color makes you look great. Make sure to wear under shirts with these because sweat stains on a button up is never attractive. As I said before, these can be worn with jeans as long as you pair it with a belt, or with a suit.
7. Black Leather Belt and Brown Leather Belt
Make sure these are nice quality leather. Also, no huge belt buckles guys. Think Cary Grant. Simple and refined. Between the two of these you will be set with any color top. Just remember that black is worn with cold tones and brown with warm tones. Since guys don't have accessories like girls do, it is your watch, belt and shoes that will define your outfit, so make sure they are nice. People do judge, and these are the things they are going to look to first.
8. Nice Leather Shoes, Black and Brown
Obviously on weekends you can throw on your flip flops or tennis shoes but you should have a very nice pair of shoes for every weekday. Studies say your shoes are the first thing people look at when assessing your outfit so don't skimp. Also, usually the pricier, the more comfortable. These are going to last you for a long time so out of everything on the list spend the most on these (or the blazer). They shouldn't be too drastic or trendy because they have to last for years. Oh! And don't forget to take good care of them, when they start wearing take them to get resoled and polished, if you go in before they get bad a good pair of shoes will last you years. I like a slight (and I mean slight) pointed toe. I don't mean elf shoes here, just a slight angle. Again, make sure too much isn't going on with the leather. And try a bunch on, some might be really uncomfortable, don't get those because you will be wearing these a lot. Inversely, don't get orthopedic shoes (you don't want to look like a grandpa.) This is a good one to bring a girl along for the shopping trip, just make sure she has good taste!
The brown pair should be a little more casual, I like the Mephisto's 'Baduard' Loafers or the Donald J Pliner 'Dugo' Slip-Ons
And for the black I like the Cole Haan's Air Gallant Wingtip Lace-Ups, they have Nike Air technology so the will be both comfortable and stylish.
9. Man Accessories (i.e. Nice Tie and Watch)
These are your version of accessories, so go all out because you don't have a lot. I like ties on the skinnier side, (not ridiculous though). When picking them out think Mad Men. And no I don't think mad men is a trend, I think that style of dressing is classic and will never go out of style. As far as watches go, I know they are ridiculously overpriced but they really are a must for men. Just buy in your budget but don't get to flashy (no diamonds, they are too effeminate.) Really shop around and find one that feels right for all occasions, both night and day.
This is optional and pricey. However, I strongly feel that every man should own their own tuxedo, simply because it makes every man look like Cary Grant. Save it for a year your doing well financially and then invest in one. When you show up to a party or wedding in one you will wow the crowd. Again, this has to last years and possibly decades so think simple and classic.