This is all great advice, and I appreciate everyone’s input. I still desperately want dark red and black shirts, as much for casual wear as for my very relaxed workplace (which I’m only at for one more month). I’m thinking non-iron cotton, no-button collars are the way to go, although I’m pretty adamant about only spending $20-$25 per shirt.
Don’t wear polyester, please.
Go to a Filene’s Basement or a Century 21.
Google “jantzen tailor” and use them (MTM shirts way cheap, good quality).
Button-down collars are less formal and a bit dweeby looking.
Cufflinks have not been “in” nor “out,” they have simply existed. French-cuffed shirts look nice, but they sound like they’re probably not your thing.
Avoid JC Penney.
Avoid blousy dress shirts. Get something that actually fits you.
Wear the type of collar that best suits your face/physical features (info available on Janzten’s website).
Tyrwhitt shirts fit like dresses.
The “shiny shirt” idea you have sounds like it might have a dated “Who Wants to be a Millionaire?” look to it. If you’re alright with that, go for it. Otherwise, stick to the classics.
I suspect that you do not wear a tie with your shirt that often. In that case I think that button down collars look more “finished” than collars without buttons. Many collars are floppy if not closed and snugged up with a tie.
Could someone explain about collars?
I can think of two kinds, the sort that button to the front of the shirt and are basically an even height all around the neck. Then there are the sort that taper to a point in front, don’t button, and are much longer in the front than the back. Are there names for these? And, is one more ‘formal’? I’ve always felt that the button collars are less snazzy-looking and are appropriate for wearing at the office but not formal occasions. The other collar (non-buttoned) is much more versitile, but sits a bit higher on the ‘formality’ ladder.
Er… I don’t quite get what you mean by “longer in the front than in the back.”
Here are the standard collars. I wouldn’t wear a button-down collar to a wedding. Instead, I’d wear a point or spread collar, depending on the tie. Big tie knot = spread, normal/small knot = point.
Spread collars are a bit more “European” looking, as well, though they’ve recently come into a bit more favor stateside.
BBVL, I’m a man who likes to dress good. I’m also under 50 (exactly half that) which is something that I’m just not getting from most of the advice in this thread (no offense to you guys!). If you follow most of the advice in this thread, you’re going to look like a stuffy, frumpy middle manager who hates going home to his thankless kids and that hedgehog of a wife.
Here’s my advice.
- Check out an H&M if they’re near you - they’re typically in malls. They specialize in cheap urban hipster clothing, but they have a “business” section as well for young urban semi-professionals. Hot stuff - you’ll look straight out of GQ, but in a really effortless way rather than in a flashy way. The shirts are $39.99 each, but I think they have a permanent “buy two for $59.99” thing. You could do a hell of a lot worse than to just go there and pick up five or six of those. They’re cut more fashionably and are available in fashionable colors and patterns - classic pinstripe and flat-white or blue, but more daring things like pale violet or pastel pink or green. They look and fit and twice as good as anything you’ll find in your average department store.
Here’s me in an H&M black pinstriped shirt, looking a bit metrosexual but still twice as hot as your average office worker. 
-
Don’t wear shirts that are too large. I see this mistake on probably 90% of guys that I see riding the El or walking around in the loop - shirts that “blouse” out, especially around the waist. A button-down dress shirt is not a t-shirt; it should not be baggy and droopy. It should be form-fitting but not tight, like this . If it’s bunching up and blousing out around your waist, you look like a clown, and it also makes shorter or stockier men look significantly fatter.
-
No button-down collars, ever, unless you want to look like the guy who comes around to service the copier or the guy in that movie Falling Down - those dinky little button-down collars are a one-way ticket to nerdville. Your collar should come to a nice point, not be rounded and dinky, and shouldn’t button down. This looks totally hot with or without a tie.
-
Most “regular” clothing stores for the 18-39 demographic have expanded to featuring hip and stylish dresswear, mainly because there was this huge vacuum there and business casual has devolved enough (and rightfully so - it’s probably the least flattering mode in existence) to allow stylishness and creativity. Check out places that cater to people that don’t have salt-and-pepper hair. I recently disovered that Express for Men - a place mostly known for their overpriced jeans and pants - has a great line of dress shirts in great colors and patterns. They’re too expensive, but I recently hit up a great sale there where they were selling the plain/flat color ones for $19.99 each, and I stocked up.
-
Though French Cuffs are ostensibly coming back, I think they make even the best-looking man look like a gay pirate. YMMV to the ninth power.
I actually like your advice, VC03, just like I like your musical recommendations. I’m 27 and don’t want to dress like I’m 47! Luckily I’m leaving the traditionally stodgy and conservative field of law, so I won’t have to worry about seemingly-arbitrary rules like “white and blue shirts only” or “no brown suits, ever” or “red ties = power.” If I can afford it, I’d love to bring some sharp retro-hipster style to the workplace.
I’ve gone with my dad to buy dress shirts many a time. He likes a cotton-poly blend, more cotton than poly, but he lives in Florida. He goes to that outlet people were talking about, plus the department stores, but he goes to the department stores when they are having sales and gets the higher-end shirts.
He bitches that nobody makes fitted dress shirts anymore. For a couple of years, that was the Great Hunt, to find the sale on the few fitted dress shirts still being made, but by now we’ve given up. Now the Great Hunt is for 60/40 cotton poly in nice colors.
If you are too… well, anyone who made it through law school without knowing how to buy dress shirts has to have turned out the kind of lawyer I’m going to be… too GRANOLA to go buy a ritzy shirt just to see what works on you, you could try going down to the thrift store and buying a bunch of different shirts, to try the different fabrics and sizes. You’d want to get measurements so you’re still in the ballpark, but shirt sizes seem to be awfully specific.
I go to the Mens Wearhouse to buy shirts for my dad, but they have a very limited number of poly blend shirts. If you don’t like ironing, don’t go there!
My dad is one of those “always sweaty, always hot” guys. The shirts I buy him are fairly thin, and he’s not overwhelmed by the heat of polyester. Actually, I found some nice ones for him at Sears. Around $20/ea. if you catch them on sale.
F’rinstance, if you are going to a lot of corporate meetings, especially with clients, then the general rule would be blue or grey suit, white or blue shirt, your choice of collars and cuff types. VC03’s shirt choice would be about as appropriate as a leather basque and gumboots.
High-powered lawyery or similar stuff would be even more conservative than the above. No button-downs, french cuffs, very restricive tie choices, shoot VC03 if he tries to come within 100 yards of the office door.
If you are working in a fairly relaxed business casual atmosphere, then VC03 would be giving you good advice. If you are working in somewhere like our back office (shorts & T-shirts allowed), then VC03 will make you a fashion god.
In general I would tend to agree with others that anything other than cotton is a bad idea, and also point out that while blue, white and maybe gray are boring, they are always appropriate in a business context, so you’ll never be forced to leave them on the shelf and you’ll be safe if you get dragged into an unexpected meeting. They are also easier to coordinate ties and stuff with if that is a concern.
While french cuffs look sharp in the appropriate context, they also tend to wear faster if you work at a keyboard a lot. Windsor (cutaway) collars look fugly without a tie IMO and not much better with one. The tyrwhitt shirts are very nice and often available at steep reductions - also, in the UK at least they will let you return any shirt that has not been worn/laundered, so you can order a few, try them on and send them back if they are not your thing or size. At $40 and a free trial you can’t really go wrong but remember the size is key.
I think the material you are referring to might be one of the superfine cotton fabrics like 180 thread count. I have a blue shirt like that which I think is Sea Island cotton - very nice material but expensive.
I’ve never been accused of being “granola” before… I assume that means hippie-like? If you knew me, you’d never say that about me. 
But I rarely had to dress up IN law school, I was smart enough to wear my more conservative stuff for interviews, half my shirts were hand-me-downs to begin with, and in my current workplace, I sit in front of a computer most of the day, never deal with clients or appear in court, and I’m the youngest person in the county and the only male in the entire circuit, so I get cut a lot of slack on my wardrobe. And woo hoo, in one more month, I’m turning my back on the entire profession and escaping!
I’m a bit of a clothes horse so take that into consideration…
I buy my shirts almost exclusively here: banana republic shirts
The are a bit spendy but when they are on sale, they are quite reasonable (I think) and the quality is pretty high. I wear them regularly for work and machine wash after each wearing. They last and keep their fresh look.
For more conservative but still high quality shirts and a pretty good description on various collar styles and range of fabric (including non wrinkle blends) I suggest: Land’s End
An excellent selection for the more conservative dresser.
You can also go into a Department store like Hecht’s or Macy’s or some similar type of store and look in the men’s department. They usually have a wide range of styles and prices. Try them on and buy what you like. Just remember, you get what you pay for and a $15 dollar shirt won’t last as long or look as good as something in the $40 and above range. It’s all got to do with thread count and fabric quality, etc…
I only shop two places for clothes. Men’s Wearhouse for the fancy stuff and JC Penny for everything else. And I don’t buy dress shirts at Men’s Wearhouse anymore because I just can’t justify spending $54 on a shirt. My other problem is that my current measurements don’t make it easy to buy off-the-rack. I’ve got a big neck and broad shoulders but it’s hard to get a shirt with the right neck size (generally a 20) without the rest of the shirt being too big. The chest especially, but the arms are often too long. This means that most of the time I have to get every shirt I buy altered, which isn’t cheap. Heck, I’ve got to get my suit pants altered for the same reason–I bought the suit based on the jacket size, which is fairly large because of my shoulders, but the pants are scaled for the jacket, making the waist far too large.
That said, I do like the Men’s Wearhouse, though I seem to quickly run up a tab without knowing it. Like the time I went in for an overcoat and walked out with my suit (including new shirt and tie) as well as the overcoat. You can get a bit of a discount though if you join their club and a little more if you get one of their credit cards. For example, if I were to go buy another dress shirt and the price was $40, I’d get a $4 discount (10%) with the club, bringing the price down to $36 and then another $1.80 discount (5%) if I used the credit card, making the price of the shirt $34.20. And I’d get 40 more points added to getting a $50 gift certificate ($500 spent=1 $50 gift certificate). So the savings can start adding up, especially seeing as how I’m not about to buy clothes on credit (especially with a 21% APR!) unless I have the cash to pay off the balance right away. In fact, I got myself a really nice jacket using a gift certificate, another coupon they sent me, the club card, and the credit card for about $20 out of pocket. (This was like an $90 jacket.)
I’ve found really great deals on dress clothes at Syms, if you have those nearby. I got two of my three suits and my badass gray trench coat at Syms, much cheaper than I would have at Men’s Wearhouse. Sadly, I never find any decent shirts there.
Jos. A. Bank has some really great shirts. The “Traveler’s Collection” is 100% cotton and wrinkle-free. They’re probably more than you’re looking to spend, but I think they’re well worth it. They look nice, and the time I save not having to iron (and embarassment I save by not wearing wrinkled shirts) is well worth it.
You should not wear cuff links or suspenders unless you either: 1.) work on Wall Street, or 2.) are extremely pretentious. If you are going to work in a more casual environment, then don’t go anywhere near cuff links. I work in a business casual office, and those that wear ties and/or cuff links are thought to be trying to hard. Get a shirt or two that you like, then see what your co-workers are wearing, and judge by that what is acceptable in your workplace.
I agree with ana/kata on the shiny or monochrome look being leftover from “Who Wants To Be A Millionaire?” One of the anchors on SportsCenter was doing this as recently as a year or two ago, and I kept wondering if he just didn’t realize the “look” had been over for a while now. Then again, it’s important to be comfortable. Any recommendation you might take doesn’t matter much if you aren’t comfortable with what you’re wearing.
Also try places like Ross, Marshall’s, or TJ Maxx.
They have name brand shirts like Calvin Klein, Nautica, Kenneth Cole, Tommy Hilfigger, Ralph Lauren, Liz Claiborne at $20-$25.
They’re the same shirts you’ll find at the department stores for $60+.
You just have to know your size and be willing to pick through them.
Or try K&G Fashions. There’s one at 4308 East Colonial, Orlando.
All my shirts are Kenneth Cole 100% cotton and were all $25.
Haha! I love it. I just wanted to say that my reccomendations are solely for a “business casual” office, not for corporate board meetings or lawyer jobs or anything stodgy and “old boy.” I thought this was implicit.
Gotta say - watch the cut / size of your shirt. The shoulder seams should be on your shoulders, not hanging halfway down your arms. Don’t go the “full cut” or “traditional cut” around the waist either, where it’s one straight seam from armpits to waist. They’re all baggy around the waist unless you’re pretty chubby. Go what’s called a “European cut” or “tapered cut” around the waist, where there’s slightly less material and it doesn’t hang out.
Hey, I like suspenders. They keep my pants up.