Dressed for Success, the Frugal Way

Anne writes in:

After searching for most of a year after getting my degree, I finally found a great job which I’m starting just after Memorial Day. The problem is that I don’t know what to wear. I don’t want to stand out as being poorly dressed but I don’t want to dump thousands into a work wardrobe. What should I do?

Here’s my game plan for this situation.

First, contact your new co-workers, particularly your soon-to-be-boss. If you don’t have this information yet, contact the company and request it. You may be able to find more of them using tools like LinkedIn.

Contact them individually, asking what normal attire is in the workplace that you’ll be joining. Ask what they wear – brands, level of attire, and so on.

You should pay particular attention to what your boss-to-be actually wears. Don’t be afraid to ask this.

Your best bet would be to dress at a level similarly to your boss, but not in a way that’s miles beyond the workers at your level. In most workplaces, you’re better off overdressing a bit than underdressing. The problem is that each workplace has something of a different definition of what “overdressing” and “underdressing” is and by finding out what your coworkers wear, you can get a bead on that right off the bat.

Once you’ve figured this out, go shopping. In my experience of buying clothes that work for professional use at good prices, I’ve found that the best place to shop first is at consignment shops. It’s often amazing how many very nice clothes can be found there. That’s where you’ll find business attire – often barely-worn stuff – from people whose life situation has changed direction, and it’s often available at great prices.

Rather than buying a lot of clothes right off the bat, you should stock your work wardrobe with fewer items that can easily be mixed-and-matched. Don’t go for the flamboyant – go for the presentable items that you can rearrange easily to create the appearance of a fresh outfit. For example, you’re a lot better off with six shirts and six ties than ten shirts and two ties – not only is the former set of clothes cheaper, it’s also easier to create the appearance of a more diverse wardrobe.

You should also be patient and be picky. You don’t have to buy everything right off the bat. Look at lots of consignment shops. Don’t be afraid to buy a few new items to mix in with the consignment items.

If you’re unsure what looks good, identify a consignment shop or two with a number of items you’re interested in and then take a friend. I usually let my wife be involved in the selection of such clothes because she has much better taste and a better eye than I do – I tend to often fall in the “if you’re clothed, then you’re good” path. Take someone along who can identify what is well-made, what items go together well, and what items simply look better than other ones.

If you’re uncomfortable dressing up for work – as I have been – do what I used to do. Put on comfortable clothes – like a t-shirt that you like to wear – and dress well over the top of that. I would often wear my favorite t-shirts and shorts under my dress clothes for work and sometimes I would literally take the dress clothes off on my way out of the workplace at the end of the day.

A final tip – it’s almost always a large net savings if you read the instructions on the tag and follow them for cleaning purposes. If you’ve got a nice wardrobe, it might seem cheaper to just wash them with minimal cost and effort, but you can drastically extend the useful life of good clothes by following the garment instructions.

Good luck.

Trent Hamm
Trent Hamm
Founder of The Simple Dollar

Trent Hamm founded The Simple Dollar in 2006 after developing innovative financial strategies to get out of debt. Since then, he’s written three books (published by Simon & Schuster and Financial Times Press), contributed to Business Insider, US News & World Report, Yahoo Finance, and Lifehacker, and been featured in The New York Times, TIME, Forbes, The Guardian, and elsewhere.

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