Right now my dress style can be accurately described as "t-shirt and jeans." I've dressed this way for my entire life and I'd pretty much like to dress like an adult now. So, men, what says: "I care about the way I dress, and you should take me seriously, but I'm still a relaxed kind of guy."

I'm open to a whole new wardrobe if it'll make the difference. :)

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I think short cut (meaning don't hang down to your knees) button up shirts and polos go a long way. Jeans are perfectly fine as long as they fit well and are in good shape. A nice pair of boots or simple flat soled sneakers also look snazzy. I have a pair of asic sneakers that are comfortable and don't look like air jordans.
I've been playing with this too this year... I had been dressing down for the last decade after a spell of doing business casual, but I feel like it is time to dress like an adult again. So, I've been trying to find something that is dressy-casual, classy yet confident & relaxed and expressive of my own sense of style. What I've done is this... giving me a range of casual to dressy to play within depending on my mood & the occasion.

I start with a nice patterned sport shirts perhaps in a softer cloth or more restrained "sharp" dress shirts or even a dressy (nice and smooth) solid-color polo

I may add color t-shirt blanks or turtlenecks under, but with the option for a tie only when absolutely needed -- this is the splash of coordinating color role for me... I'm really not much of a tie guy (although I can tie them quickly and properly when I need to)

If it is cold, I may be adding a v-neck light 'layering' sweater or sweater vest over with the option if I want to perhaps go into a dressier "formal vest" look if needed (though that is not yet a part of my wardrobe)

I add good jeans (I agree with these needing to be "good fit, good condition"), cords, khakis, or chinos (& maybe moleskins), with the option to use dressier pants if needed. But even then I'd probably hold off on proper matching garments so it stays just a bit more casual than a true suit unless I really did need to do the full suit look.

put on the bottom my 1460 Docs, Ben Sherman chelseas or "fashion" Chucks or casual loafers, boat shoes or "buck" oxfords with the option to do dressier oxfords when truly needed.

finish off with a nice sport coat (but nothing too suit-like, so herringbones, glen plaids, houndstooth & checks, soft cashmere blends & camel hairs for this time of year & linens and seersucker in the Summer)

cover with a leather 3/4 coat or full-length woolen topcoat now that it's colder, trench when it's rainy but not cold

and finally it's topped off by either a wool or fur felt fedora of some sort now that it's cold, an ivy/flat cap if it is windy, or a straw fedora in the summer. coordinating colors of course.

That may well be overkill for what you are after, but there must be elements in it that could work for you. If nothing else, it may be helpful to know that some of the elements that were already suggested can be used & even pushed this far into "dressy" territory and work nicely.

good luck!
-j
I think these are all wonderful suggestions. I suppose "business casual" is probably JUST slightly above what I want to do. Basically I want my clothes to make a lasting first impression (and a favorable one) without saying "This guy looks stuffy."

I'm kind of envisioning that this will end up with khakis for me, because I view them as more.. I guess you could say "refined" than jeans. It's these kinds of decisions I want to make. I want to look like I take myself, and my style, pretty seriously and actually do put effort into it.
I don't know what your personal style is, but there are plenty of options out there that hit the edge of business casual, and can draw on other eras if you like...

I know several people (20-somethings who are shorter/slimmer builds) who dress in a retro-style, doing a "Mod" sort of look from out of the 60s making use of slim-fit straight-leg jeans, tucked-in slim-fit Ben Sherman style button-down shirts (usually patterned), chukka or chelsea boots or plimsole/chucks, tighter fitted/waist suppressed casual sport coats (from off the shelf at H&M typically rather than true vintage or modern bespoke, they're college kids after all so $ is an object), barracuta harrington jackets or older style leather coats or military-ish wool coats. They always look "sharper" than those around them who are dressed more "college kid casual" with tons of identical A&F or whatever bits, if you know what I mean.

But it's also not like a "costume", they pull the look off by really being into that era & paying attention to details so everything sort of end up working together even with some more modern bits mixed in with the more vintage looking bits, so it looks really natural.

If that look isn't what you're into, you might want to look into the slightly more recent "football casual" stuff -- Barbour brushed cotton pieces... they slot somewhere between oxford cloth dress shirts & the heavier 80s grunge/indie flannel stuff. Classic checks or tattersall designs usually. Or Polos. nice trainers. Classic british outerwear like waxed cotton jackets or tweed duffles.

Again, a look that comes off as more "put together" than most peers, and if you really click with the pieces you can sell it as being a genuine expression of self rather than "costume". It all depends on how comfortably you wear what you do, and that goes equally for the difference between someone who "dresses well" with items he's totally comfortable in and would wear without needing a reason vs. someone who "dresses up" & always seems uncomfortable... like the teenager who's in a dress shirt and wearing a tie for the first time in a year for "school picture day" or whatever and just looks completely uncomfortable & awkward.

I know some 30-somethings doing this since their bodies are no longer shaped quite right to stay "Mod". =-) Of course, neither are their hairlines, so they rock out tweed ivy/flat caps to cover the inevitable thinning up top.

Maybe it would be worth checking out some of the recent "looks" in men's clothing to see what really clicks for you? (grab some old GQs?) Then use that as a guide to picking up a few key pieces to take what you now have in your wardrobe and begin changing its course toward the look you'd like to do? Of course, you should consider your scene ... if you are in College or if you are just starting in the work world, the look might need to be a bit different. And think about your peers ... how are they dressing? what do you like about it? what do you dislike? (ugh, popped collars, agreed!)

I hope that is of some help...
I try to typically dress for utilitarian purposes: ie. cargo pants, boots, t-shirt, over shirt that can be worked in if need be. I know it's goofy, but it always seems to work out. I can even dress this way for nice occasions. I keep my boots looking somewhat presentable, my pants aren't all stained up and they are usually natural colors, and my shirts (not t-shirts) are button up flannels or canvas that can be tucked in for more formal events. Not trying to offend anyone, but I always get a kick walking through clothing stores and seeing all the cheaply made, "foofie" trendy items that would rip as soon as you had to bend over and pick up your keys. Oh and the pre-worn clothing....gimme a break.
You want to be careful not to be too 'dressed', or you'll be in the same boat that I am. I decided recently that I wanted (or should, rather) to dress more my age as cargo shorts, jeans & tees, etc made me feel like a boy. Since I was already working to improve the quality of clothes I wore to work, I started to incorporate some of that into my 'off' time attire.

Let me just share a post I made yesterday at B&B regarding a similar issue (someone was wondering how to dress for casual wear):


[quote]Originally Posted by StylinLA View Post
You can't put on a pair of wing tips and a button down oxford cloth shirt with a blue blazer and expect to get any 27-year-old women "hot."[/quote]

My (~ex-)wife (who is 29; I'm 32) and I met up Wednesday to do some Christmas shopping with our daughter. We're on friendly terms so she was making some half-joking/half-serious comments about finding a new girlfriend. As I was picking up a couple new OCBDs, she pointed out a couple shirts that thought would look good on me. I passed on them and commented that they were too urban/metro for my tastes and she responded, "I'm just trying to help you get away from that Bible salesman/Brawny Man thing you have going on".

To make matters worse, we later stopped in Belk and I got a wink and a nod from a gentleman who appeared to be in his late 70s because we were dressed identically... (black loafers, khaki dress slacks, shirt & sweater, flat cap) This only cemented her point.

So while I'm unable to offer advice and look forward to hearing what others offer up to you, StylinLA is on to something.
I don't know ... I'm just entering my 40s and I always take it as a compliment for older professional gentlemen (professors, lawyers, judges, business owners, doctors) & women on both sides of my age to take notice of my dressing nicely or make a comment. Perhaps the edge of 30 is different?

It might have to do with dressing appropriately for the occasion? If the "business look" of wing tips, oxford & blue doesn't fit the purpose (trying to get a 27 y/o woman hot), then it doesn't fit & another look might be needed. What you wear out to a fine dinner with your date/partner isn't what you wear out to the club filled with available women, but it might be what you wear to a young professional's mixer (where getting that 27 y/o hot might be a nice added benefit of looking good among your peers). I think that dressing well will eventually land you the 27 y/o who finds that look hot & that might be a better long-term fit than most. But that's just my opinion...

Still... if you aren't into trendy/metro stuff, that's fine. Classics are classics and have been for a very long time for good reason. Yet, I think the idea is to work with classics and contemporary things & modulate the "dressiness" appropriately to always look good but also look comfortable. What's wrong with mixing something trendy deep toned or satiny stripy with more classic pieces? Nothing. If it looks good, if you feel comfortable in it, then it's good.

For that reason, I do allow some drift in my style... picking up on some classic style and then modulating it to fit my own personality better.

I might do "Southern Lawyer" but only in part, with a classic blue & white stripe seersucker coat ... then put that over a casual tee-shirt blank in some complimentary color & classic Levi's jeans & then wear my straw fedora & comfy shoes, maybe even sneakers rather than the full-suit w/ white bucks look.

I might do "Miami Vice" but again, only in part ... yes, that is a cream linen coat but I'll dress it up/down differently depending what I'm doing. Some times it's time to dress up (summer-time social occasion) & I'll work with some sort of interesting textured shirt in a complimentary color (since you can't layer in summer and I'm anti-tie working with both color and texture in the shirt seems key) & put together a dressy outfit, other times down (just walking about town, sitting down outside for coffee, etc) & it might be slightly worn jeans (not ripped, just faded & with character). Odds are, I wouldn't ever go linen pants & sock-less loafer like Crockett & Tubbs even if I am doing a tee under (and more so if the tee is in a pastel shade).

At this time of year, I'll mix the more patterned "sport shirts" (the distinction between dress and sport shirts is sometimes arbitrary in my mind) with the more classic looking sport coats in a similar fashion to get to the dressy-casual spot I like.

Sure, I can always do a more dressy/formal look when needed, but that's it... when needed. For a funeral? It's time for the "60s G-man look" ... that semi-formal look of black coat, black tie, crisp white dress shirt, black pants, black top coat, & black fur felt fedora (and white scarf if you need it). For work? Great time to play with fall colors in shirts & tweeds... hinting at the "english country gentleman" look maybe with a classic country check sport shirt, earth-toned hacking style sport coat, etc. but not doing it completely. Always modulating to keep it appropriate, unique and uniquely yours.

It works for me... your mileage, of course, may vary. =-)
I was walking in your shoes a short while ago and I think Todd's nailed it here: ditching your t-shirts for collared shirts and somewhat dressier shoes will probably put you ahead of 80% of your peers without making you feel like you're trying too hard. I'll add in that if you go for a polo shirt, it shouldn't be a logo'ed golf shirt.

I'm not a fan of wearing athletic shoes outside the gym or hiking shoes off the trail, but if sneakers are your thing, simpler is probably better.
I agree with the "no gym sneakers" rule. But canvas lowcut sneakers are a good match with a pair of well-fitted jeans.
Agreed...
If they really only look right on the court or on the trail, that's where they should stay. =-)

If you can get some good canvas, leather or suede low tops in "fashionable" sorts of color schemes (monochromatic or complementary color schemes especially in good solid easy-matching neutrals), that works (I do it too). Ditto for using working man's boots (like my 1460 Docs). It adds a more casual & "younger" element to the look.
I think whatever you wear the biggest issue is to make sure it fits correctly. A well-fitted t-shirt looks better than a baggy buttondown.

Also, I'm not a fan of kakis. Cords and jeans for casual and dress pants for more formal. I put kakis in the same pile as shorts, sandals, and short sleeve button-downs. Unless you're chasing Rommell across North Africa with Montgomery, you shouldn't be wearing them.

Finally, more of a personal choice but I'm not a fan of tucked in unless I have to (ie more formal or I have a sports/dinner jacket on). I think if you keep your shirts ironed and the tails don't go to your knees (as someone already mentioned) then untucked looks fine.
My problem with "tucked in" is that it REALLY exposes the fact that I have a skinny build. My waist size is about 30". I look skinny even untucked, but man.. tucking makes it worse.

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