Help me dress like a grown-up (but not a geezer)

March 23, 2010 3:30 PM

Last month, I finally landed my first "real" job. However, I have no idea how to dress myself -- I need to look "smart," but not overdressed. Give a geek some fashion advice!

I somehow managed to slip by for 22 years without ever having to learn the nuances of proper business attire. I'm certainly no slob, but at the same time, I can't help but notice that my appearance is decidedly "frumpy," despite my best efforts to the contrary.

I'm an entry-level sysadmin, and as such, very little is expected of me in terms of attire (In fact, there is no dress code that I'm aware of). Although this grants me lots of flexibility, I have no idea where to start, or how to not look like every other IT nerd in the building. Most of my IT/Engineering colleagues put on an ill-fitting, neutral-colored button-down shirt, a pair of slacks, and call it a day.

On the other hand, everybody else in my workplace dresses extremely conservatively (I work for the US Senate). Although I have no desire to look like a Senator or a staffer, these are sensibilities that I need to take into account. Also, a full suit isn't exactly practical for some of the duties that my job entails.

I need to find a happy medium, where I'll look professional/impressive to both my coworkers (who are underdressed) and "clients" (who are overdressed).

I've gone through a few blogs (ie. Put This On), and although I can identify what looks good, I have a tough time taking away any specific and useful pieces of advice that won't also bankrupt me.

FWIW, I'm male, 22, 5'7", 145lbs (ie. slimmer than average), brown hair, blue eyes, enjoy long walks on the beach.......

posted by schmod to clothing, beauty, & fashion (34 answers total)

Dockers + dress shirt is a good start. Shoes like Doc Martins or Sketchers.
posted by jockc at 3:36 PM on March 23, 2010 [1 favorite]

Think about this in terms of future goals. You presently work for the US Senate, but you don't work on the political side of things.

Do you want to work in politics in the future? Do you want to stay in IT? If you want to stay in IT what aspect of IT do you want to work in? IT for a defense contractor, for example, is a much more conservative culture than a web programmer for an ad agency in Portland, OR.

The best rule of thumb I've heard is "dress for the job you want, not the job you have." Look at your boss (assuming he's male). How does he dress? If he dresses well, emulate his style. If not, then find another person at his level who you do think dresses well and emulate that.
posted by dfriedman at 3:39 PM on March 23, 2010 [1 favorite]

dress shirt, not buttoned all the way up, and a jacket on the back of your chair for emergencies of a formal nature.
posted by Billegible at 3:40 PM on March 23, 2010

Fitted dress shirt + any sort of dress pants + shoes made out of cows (nice boots work, any dress shoe, maybe not oxfords). Have a jacket around, make it navy. Also, don't be afraid to wear a tie or a vest occasionally; they allow you to add some color to your wardrobe. Guys don't get many accessories. Most of my colleagues have roughly the uniform you described: dress shirt + slacks, no tie. I wear a tie for the color, but am an outlier in doing so.
posted by craven_morhead at 3:46 PM on March 23, 2010

I often wish that instead of the Pony-tail Guy™ look I went with by default, I had adopted the Joe Celko method of six identical black three-piece wash-and-wear suits.
posted by ob1quixote at 3:48 PM on March 23, 2010

To me, the number one factor in looking professional is fit. If your button-down shirts and dress pants fit you appropriately you will look professional. Making a trip to the tailor after you go shopping could help a lot.
posted by shesbookish at 3:52 PM on March 23, 2010 [4 favorites]

I can't tell if ob1quixote is joking or not. But don't wear black suits.
posted by ewiar at 4:04 PM on March 23, 2010

What shesbookish said. You can get the right button-down shirt and Dockers, but if we see your socks and your chest hairs poke out when you lean over, something went wrong.

Go to a store with the right kind of clothes and admit your cluelessness to someone working there. Describe your work situation. Pick a confidant who dresses "smart" and doesn't have a perma-smirk or perma-scowl. You'll find that quite a lot of these people really like their jobs, and enjoy picking out good stuff for other people. (Nordstroms in particular is fantastic for doing this, but you will be paying for it on the sticker price. You don't have to go that high end for this kind of help, though.)

Once you have done this a couple times, you can either get the hang of doing it for yourself or maintain a relationship with one particular employee (especially if their salary is partly commission-based.)
posted by whatzit at 4:04 PM on March 23, 2010

shesbookish, so true.

OP, you don't need to spend a lot of money or shop at designer stores to look sharp and well put-together. Stores like H&M will have a great selection of affordable trousers and dress shirts in modern cuts.

A slim cut shirt tucked in looks great - leaving your shirt untucked is for going out clubbing, and you definitely want to stay away from those old-school poofy, blousy shirts. Get pants that fit propertly (you should not need a belt to hold them up) and take them to a tailor to hem them so that they break properly - don't leave them all bunched up around your ankles.

You only need two nice pairs of lace-up leather shoes - black and brown. Learn how to match them to different colored pants.

You can always throw on a nice sweater or sweater vest (fine gauge cotton or wool), or a blazer over your shirt to mix it up a bit so you don't feel like a cartoon.
posted by keep it under cover at 4:12 PM on March 23, 2010 [4 favorites]

Fit is important as is how well you take care of your clothes. Making sure everything is pressed and crisp will go a long way. This might just be me but for some reason, I think stripes always look smart. I think your everyday look should be dress shirt, tie, pants with a belt, nice shoes and proper socks. Khakis or Dockers are fine but I would also get some non-cotton pants like a lightweight wool.

I think you can do well by going to Express and they always have sales. You can also get good clothes at Banana Republic and J. Crew. The former has more frequent sales. There's also Joseph Bank which always has sales but at the same time, my father shops there so the style may be lacking.

You can't go wrong with a blue shirt and khakis but I recommend wearing a suit or at least a jacket once in a while. It might just be me but I think it keeps your colleagues on their toes :) Also, don't be afraid of colors and prints. I have a lot of respect for a man, especially on the Hill, who doesn't look exactly like everyone else. That said, I wear black or gray pretty much every day to work so maybe you shouldn't take my advice. Good luck!
posted by kat518 at 4:14 PM on March 23, 2010

You mention your coworkers wearing button-down shirts and slacks, which has basically become the default attire for North American office workers, but realize there are a wide range of possibilities here.

Wear an oxford-collared shirt, belt, slacks, and nice shoes. Both the shirt and pants should fit you well obviously - this means that the shirt doesn't look like a tent (look for "slim fit" cuts) and the pants aren't baggy or stacked up around your shoes.

Personally I think it's much more important to have pants that fit you well as this is often overlooked and for shorter/skinnier guys (I'm about the same size as you) it can be difficult to find pants that fit well.

If you say that you're "frumpy" you may not have a good idea of what "well-fitting" looks like as a lot of guys (especially skinnier guys) are accustomed to wearing clothes that are too big for them, so I'd recommend asking a more stylish friend for advice or maybe spend some time browsing styleforum/superfuture etc. to get an idea.

Slim fit dress shirts from H&M and Uniqlo are a good deal - they're really cheap but fit skinny guys well. I've had friends who only wear RLPL and Brooks Brothers compliment me on them.

For pants I've had luck with Zara, Club Monaco, and surprisingly Banana Republic. Look for "tailored fit" or something similar on the tag. Most of these places will hem the pants for you as well. Well-fitting pants will cost you more than shirts but you only need 2-3 pairs. I would tend towards darker colors. Don't wear Dockers as they are embedded in our collective consciousness as the chosen pants of Best Buy workers everywhere. (But obviously if you find a really well-fitting nice pair of khaki pants then go for it).

In general, for shirts and pants the fit is more important than anything else and you shouldn't be buying expensive clothes that fit poorly. Brooks Brothers shirts for example are renowned for fitting like tents on skinnier guys as they're intended more for overweight middle-aged men.

Shoes: Unlike shirts I think it is actually worth spending more money on quality shoes since you will only have one or two pairs of dress shoes. Lots of people wear Allen Edmonds - the Park Avenue is a classic and should give you an idea of what you're looking for. Steer away from big ugly loafers, square-toed shoes, and under no circumstances wear those chunky sneaker-soled dress shoes I often see IT guys wearing.

Also, IT guys shouldn't be wearing suits to work obviously.
posted by pravit at 4:14 PM on March 23, 2010 [3 favorites]

Also! Also! Avoid stripey dress shirts. Solid colors, interesting textures, or check patterns are nice.
posted by pravit at 4:25 PM on March 23, 2010

If you're going to wear Dockers, and they're cotton, be sure to iron them. Same goes for dress shirts. I know that man-made fibers are anathema to some, but a few blends and "wrinkle free" items that can go directly from dryer to work can do wonders for you.

Make sure everything fits, everything is stain-free, and wearing an undershirt makes everybody happy.
posted by xingcat at 4:25 PM on March 23, 2010

I'm the same build as you are, banana republic (on sale!) shirts look very good. Go with a trusted friend who has some fashion sense.
posted by defcom1 at 4:28 PM on March 23, 2010

It may go without saying, but just in case: If you do wear a button down shirt, do not forget an undershirt!
posted by pazazygeek at 5:00 PM on March 23, 2010

Similar questions get asked about once every two months, so you will find some helpful suggestions if you search the archives here. Sorry I can't help with that right at the moment, but if I'm procrastinating later...
posted by salvia at 5:04 PM on March 23, 2010

Some great advice so far. Much appreciated!

Re: Dockers & Button-Downs: This is more or less my current routine. I guess I should've stated more clearly that I'm not completely devoid of style. I've been conscientious enough to iron my clothes (although I'm admittedly new to this as well, and need to master the technique a bit more thoroughly). I can generally tell whether or not an outfit is "working" for me -- getting there is the problem.

My primary problem is making things fit properly, and "click" as an outfit. Ties in particular seem to be an achilles heel.

I was able to figure out how to look good in the context of my fellow undergraduate Physics majors while in college -- figuring out how to earn the respect of my age-40+ colleagues in IT as well as the ridiculously overdressed 20-something staffers in the office has been a completely different ballgame. I'm trying to be respected both socially and professionally. I should probably mention that I'm still new to town, and that "friends with style" haven't materialized just yet.

The Banana Republic suggestion isn't a bad one, and the few things I own from them do seem to fit rather well. Unfortunately, for whatever reason, I've found their in-store selection to be...sparse on many occasions. I did most of my shopping at J.Crew for the past few years, but am slowly drifting away from it, as most of their (rapidly shrinking) Mens' selection is either too casual or too expensive, and seems to wear out a bit too quickly. I'll give H&M a shot, and make a trek to Uniqlo the next time I'm in NYC.
posted by schmod at 5:17 PM on March 23, 2010

Slim people like you should never wear pleated pants.
posted by Sfving at 6:18 PM on March 23, 2010

Check out this site: http://putthison.com/ It will give you some ideas on dressing like a grown up. As was said, dress for the job you want, not the one you have. Pinging on your boss other other higher up, and dressing like them can be good advice as well. Good luck. :)
posted by PlutoniumX at 6:20 PM on March 23, 2010 [1 favorite]

Do NOT get pleated dress pants. They're for old guys. Dockers, for example, sells some nice slim fit pants which should fit your frame nicely (also very good price!) They won't look like skinny jeans, just not baggy. Always get slim/fitted button down shirts.
I wouldn't bother with ties on a daily basis. I also recommend wearing undershirts beneath your button-downs. They make the outfit look much more "put together".
posted by Neekee at 6:25 PM on March 23, 2010

Great advice in this thread. I came in to talk about fit, but since that's been covered, I'll add this. Never underestimate the style of really good accessories. I tend to rely on modern glasses and a very understated but distinctive watch.
posted by advicepig at 6:40 PM on March 23, 2010 [1 favorite]

My primary problem is making things fit properly, and "click" as an outfit. Ties in particular seem to be an achilles heel.

At your size you should be wearing the smallest size the store has available - I'm the same size as you and I'm an XS at Uniqlo and it's a Japanese chain for crying out loud.

I would raise my eyebrows at an IT guy wearing a tie but I don't know what the dress culture among Capitol Hill technology staff is. FWIW I work on the trading floor of a bank and I've never seen anybody wearing a tie, not even senior MD's.

The corollary to wearing undershirts is that your undershirt shouldn't be showing at the neckline unless you want to look like a drill instructor. Personally I always wear V-necked undershirts to avoid this.
posted by pravit at 7:07 PM on March 23, 2010

Are you a personal, a committee, or support staffer? If it's either of the first two I'd say you need to step it up a notch (i.e. wear a tie and have a jacket handy). The culture varies a little from one office to the next, but check out what your coworkers are wearing and don't go too much more casual. When I worked in the Senate, our IT guy definitely wore a suit at least sometimes - I know the idea of an IT guy in a suit is kind of funny, but a lot of people on the Hill are going to assume that your level of dressiness = level of respect for your boss and your job.
If you're support staff, disregard everything I said and just read the advice upthread; it's mostly good stuff.

P.S. Love being casual? Come to the darkHouse side, we have jeans days galore.
posted by naoko at 7:35 PM on March 23, 2010

Disclaimer: I'm a woman.

For tips on dressing for your body shape and developing a sense of style, look for books about style for men. On Amazon.com I noticed Esquire, AskMen.com, and Details have all published books on this men's style.

Maybe the guys here can recommend some good MEN's websites & magazines for style tips? I noticed Trinny & Susannah have advice for men for dressing by body shape, but it seems overly simplistic. Blergh, I don't like how they recommend "logos" for thin guys. Logos?!? Their women's tips are much more helpful.

Also what I've found helpful ---
-- Figure out what colours look really good on you e.g. look into complexion colour analysis. Start incorporating these into your wardrobe, especially into anything you'd wear near your face (shirts, ties, hats). The wrong colour can make you look sick or like you never go outdoors.
-- If you wear a really bright colour or visually interesting shirt, wear it with neutral pants (but usually black can be too harsh, even dark grey or brown might be better). Or visa versa: wear patterned pants with a neutral or simpler shirt.

PS -- My husband is a sys admin. I am a little confused why so many people are talking about suit jackets and dress pants. What proportion of your day-to-day work is not-so-clean work?... If you're crawling around a server room, you'll get your suit jacket dusty and rip your pants while carrying computer cases. Proportion how many casual vs. business casual vs. suits you have accordingly.

Hope this helps!
posted by SarahbytheSea at 8:36 PM on March 23, 2010

Check out Askandyaboutclothes.com. There are a lot of good guides about what to wear and matching patterns. If you go to the forums section, there are many old discussions about what to wear and finding the correct fit. They will also give brands and stores to look for.
posted by mtheshark at 8:53 PM on March 23, 2010

Try this: Step into a trendy menswear store and wait approximately a quarter of a second before a bubbly store attendant asks you if you need a hand, then ask her to give you a wardrobe makeover and tell her your budget.

Also, always make sure your clothes are washed and un-perspired on and your hair is tidy like Matt Damon's.
posted by foxy at 9:34 PM on March 23, 2010

You don't have to wear ties. In fact, I like the alternative: the sweater over a button up method.
posted by shesaysgo at 9:41 PM on March 23, 2010

Seconding shesaysgo - I do love a man in a nice sweater.
posted by naoko at 10:13 PM on March 23, 2010

My husband buys most of his pants at Banana Republic or at Calvin Klein (is there an outlet near you?). The selection of button-down shirts is not so great at these places, but there are a lot of options in a department store, don't be afraid to open some up (if possible) and try them on. For example, just today my husband wore one of the Roundtree and York brand, and it looked really good. This and other brands have some regular boring shirts but also a few cool looking ones, and department stores have sales all the time. (That specific brand may be for Dillard's, I think.)

Also, a few sweater vests in cool colors could be a good match between conservative-looking and good-looking.

Oh yeah also, from a woman's point of view (of men): khakis just look good when they've been recently washed and ironed. I say go for darker colored pants that have some sort of synthetic fibers so that they last longer in between washes.
posted by CrazyLemonade at 11:56 PM on March 23, 2010

Oh by the way, my husband's in his late twenties and works at an office, doesn't have to wear a suit most days but still has to keep it sort of formal, he started out as an entry-level sysadmin too, (hopefully you'll dress better than him in those days)...just fyi.
posted by CrazyLemonade at 12:01 AM on March 24, 2010

If you're looking for examples of full outfits that "click," it may be worth checking out Esquire's Big Black Book; it's their yearly style guide, and I think a new one is due soon.
posted by craven_morhead at 8:19 AM on March 24, 2010

The Banana Republic suggestion isn't a bad one, and the few things I own from them do seem to fit rather well. Unfortunately, for whatever reason, I've found their in-store selection to be...sparse on many occasions.

If you have clothes that fit well from them already, then you should be able to shop online easily. The selection is generally much larger.

Also if you find shirts that fit you in the shoulders, but are tenty through the torso, you can have them taken in at a tailor for cheap.
posted by grapesaresour at 5:19 PM on March 25, 2010

Update: Put This on has published an article on this very subject.
posted by schmod at 10:37 AM on April 14, 2010

Update II: Still haven't been fired for a dress code violation. Guess the advice is working ;-)

Also, there's an absolutely gargantuan thread about this topic on Reddit right now.
posted by schmod at 1:18 PM on January 27, 2011