Dress for Success on the Cheap

anchormanIt has been said that this is the worst time to obtain employment as an attorney in recorded history. The natural question that arises from such a predicament reminds me of this timeless exchange:

Champ: “What are we gonna do?”

Ron: “There’s only one thing a man can do when he’s suffering from a spiritual and existential funk.”

Champ: “Go to the zoo, flip off the monkeys?”

Ron: “No, buy new suits.”

All: “Yea!”

Hey, you gotta look good while going to those interviews, don’t you? Projecting a serious image on a tight budget can be difficult, and doing so is of the utmost importance if you want to land a job ahead of the next guy. So here are just a few tips to help you dress for success and on the cheap:

Find a Good Tailor

A well-tailored suit is the key to projecting a confident, professional image. A good tailor will have people thinking your $250 outlet store suit is straight from Polo Black Label. Have him (or her) take proper measurements, and when the time comes, take your newly purchased suit in for alterations. All suits need altering. It is just a fact of life.

Stick to the classics

Remember, you are a lawyer, not an investment banker. No raspberry pinstripes, please. Keep it simple. A young lawyer can get away with three, maybe even two well-tailored suits. You can never go wrong with navy and a darker grey. Throw in a khaki suit for the warmer months if your budget allows.

Ties and shirts for variety

Marshalls has incredible deals on namebrand ties and dress shirts for as little as $12. Believe me, I have a couple $90 ties (gifts), and I can’t tell the difference, and neither can anyone else. Three white shirts with a couple light and dark blue thrown in for good measure should provide plenty of variety. If you have a fairly tapered waist (the “V” shape), buy an “athletic” cut shirt, otherwise you will look ridiculous. Spend a little more on wrinkle-free shirts that can be thrown into the washing machine 4 or 5 times before having to be dry cleaned. You will find that the lower dry cleaning bill will completely offset the upfront expense.


One black pair and one brown pair of shoes are all you need. Great deals on shoes can be found at outlet malls. Zappos is a great place to find solid deals on both men’s and women’s dress shoes. You don’t have to spend $100 per shoe either. I have a pair of $60 black dress shoes that have lasted me 5 years.

If you want to keep it casual and comfortable you may even consider picking up a pair of mens loafers.

Save the pimp suit for Halloween

If the shoulder pads are protruding beyond your deltoids, it is too big. Shoulders are one of the most difficult places for a tailor to alter, so make sure the jacket fits snugly in the shoulders. On that same note, do not stray any further than an inch or two on pants length or waist. The jacket should be easy to button across the chest, but not so easy that people think you have been raiding William “The Refrigerator” Perry’s closet.


Do not break the bank on a $100 belt. A good belt can be had from any outlet mall or department store for as little as $15. One black and one brown belt are sufficient. Don’t go for the two-in-one transformer belts. They do not last.

Dry Cleaning

A suit does not need to be dry cleaned every week. Neither do your shirts. In fact, a suit should not be dry cleaned more than a few times per year. Wearing proper undergarments will prevent your bodily funk from infiltrating your wardrobe. Dry clean your slacks and jacket at the same time. Cloth fades just a little bit every time you dry clean it, so by taking both pieces simultaneously, they will hopefully fade uniformly.

(photo: http://www.everystockphoto.com/photo.php?imageId=632870)


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  • Great tips, Will! I would add not overlooking the value of buying a sports coat and several pair of slacks instead of always buying suits. If a pair of suit pants gets ripped or stained, the whole suit is worthless. A pair of slacks can be replaced much cheaper (also keeps those dry cleaning costs low). Except when they’re going to court, most lawyers wear their suit jackets to the office, take them off, and put them back on when they go home. I try to save the suits for court.

    Shirts should be cleaned after a full day of wearing. They may not stink or have stains, but over time sweat and grime marks will build up on the collar and cuffs. Also, always wear t-shirts under dress shirts, winter and summer, to protect the shirts from grime and keep you warmer in winter and cooler in summer.

  • I don’t disagree with your advice about shoes, except that making certain you are buying a pair of $50 dress shoes that will last for 5 years is difficult.

    On the other hand, spending $200 (or less on clearance) on a pair of Allen Edmonds virtually guarantees a good looking pair of shoes for up to 10 years. For $100, you can even have them re-crafted every decade to keep them going almost infinitely.

  • Will Geer

    Good points guys, and I particularly agree with Eric’s advise to purchase a few sport coats and slacks.

  • One tip I have gotten, but not yet used, is to buy decent-looking wash-and-wear shirts and have them tailored. Brands like Van Heusen are also selling some pretty nice-looking wash-and-wear shirts these days, far removed from the old Arrow shirts from a decade ago.

    This solves two alternative problems: (1) the cost of professional laundering (and the stretched shirts); or (2) the annoyance of ironing your own shirts.

  • This discussion is great! I echo Eric’s comments about sport coats. They are much more versatile than suits. I even wear mine with jeans some times when I can be a bit more casual. Sam: as far as I’m able to tell, the only lawyer fashion advice you’re qualified to give is about hoodies, t-shirts, and sandals :-)

  • Rather than buying low-quality dress shirts and paying to have them tailored to fit, I get my shirts custom tailored for $50 each from TailorStore (in Sweden). It takes a little more time and effort, but is TOTALLY worth it.

  • Leora Maccabee

    Gentlemen, I have to admit my disappointment in the gendered nature of this post. What about dress for success tips for female attorneys? Here’s my advice for the ladies, culled from a summer at a medium sized firm, and legal internships with a non-profit, federal judge, and government agency.

    1) Suits are essential. Get them in 3-pieces if you can, so you can wear the same jacket (because they’re always so pricey) with pants, or skirt, depending on the season. You need to own a black suit with pants. Don’t buy skirts that rise above the knees; they are too flashy and sexy for you to be taken seriously. Even The Limited or Express (where I’ve gotten some of my suits) usually have longer skirts available – and if they don’t, head to Macy’s.

    2) Shoes? Don’t ruin them by walking from your car to your office on our city streets. No one will look at you funny if you wear flipflops or tennis shoes for four blocks, and then change into your heels or dress flats across the street from your building. This will allow the shoes to wear longer. If you’re buying shoes on the cheap, I’m a fan of DSW and Marshall’s.

    3) Makeup matters (lipstick especially), and the best lipstick is the stuff that won’t wear off while you’re eating. I personally prefer Mac’s Pro Longwear Lipcolour, but any lip stain product will do. This is an area where spending the extra money will go a long way.

    4) As for style and shirts, women have more flexibility than men. My general thought is that if you’re under 35, or look young, you should dress more professional – button up shirts in fall and winter, and simple, one-color shirts under your suit jacket. However, if you’re older, or already established as an attorney, I think you have more flexibility in your outfits since you need to prove yourself less. Get a little more color in your wardrobe. Wear fewer suits and more floral or patterned outfits. Please note – women of any age should avoid the lacy undershirts that stores like The Limited and Express sell as work-wear. That may be “professional” for other fields, but not in the legal world.

    Any tips I missed ladies?

  • Thanks for your additions, Leora! I am woefully inexpert in matters of womenswear.

  • Chris_

    Aaron, thanks for that tip about Tailor Store — looks like a really, really good deal………

    • Chris,

      I found that TailorStore is not only a great deal (their $12-$20 ties are comparable to $100-$150 ties at retail), but you can also be tastefully creative with your made-to-measure designs. For instance, I sometimes like to add contrast stitching to button holes or colorful fabric for cuff and collar interior linings.

      One note: Because they are based in Sweden, shipping and tariffs add modestly to the price.

  • Will Geer


    Great tips! I was actually contemplating adding a disclaimer at the end regarding the gender-biased nature of my post. It was something along the lines of there being no women’s clothes in my closet :)