Shopping when you hate to shop

Part of spending our 168 hours wisely is figuring out what we do best. An equally important part is to figure out what we don’t do well and, if it still needs to be done, figuring out a way to minimize or outsource it.

Clothes shopping falls into the latter category for me. Over the years, due to a combination of shortsighted frugality and style blindness, I have packed my closet with a plethora of cheap clothes I don’t wear. I don’t even want to think about all the time I have spent earning money to buy clothes I no longer like because of this philosophy. While buying $20 shirts seems like it would be a better deal than buying $100 shirts, if I buy 10 $20 shirts and wear none of them, I would have been better off buying one $100 shirt that would see the light of day.

Indeed, I would have been better off paying someone $50 to choose that $100 shirt for me. This is particularly the case if I actually need to look nice for something. So over the past two years, I have gotten my head around the idea of hiring a personal shopper.

As I write in 168 Hours, there are lots of parallels between professional styling and writing. Because anyone can write, and anyone can pick out clothes, most people assume they do it just fine. They’re wrong. Hiring an editor to polish your cover letters can save you a lot of time, and possibly land you a much better job. Likewise, hiring a stylist can save you time and, depending on your personal habits, money.

So my new approach is to, rather than dribble out money on some low-quality garment every week or two, shop for clothes only once a year, if feasible. And for the past two years, I’ve been asking Lindsay Weiner, owner of a company called Style Me NY, to tag along on these massive trips.

Weiner, a Fashion Institute of Technology grad, was formerly an off-camera stylist on What Not to Wear.  In 168 Hours, I chronicle our experience shopping for maternity clothes last May. This May, we got to expand our horizons a bit since I have (mercifully) stopped expanding. Of course, being able to fit into regular clothes creates another kind of stress. There are thousands of stores in New York. How do I know which ones to hit?

But Weiner does, and this is what makes shopping tolerable for an anti-shopper like me. We met in Soho yesterday, with a list of stores (J. Crew, White House/Black Market) that she felt matched my “style” (ha) and budget. She knew where they all were. She knew what they specialized in. She pulled items off the rack I never would have chosen, and (nicely) shooed me past other items that, for a variety of reasons, would have been a bad idea. The result from a little over three hours of shopping? Several speaking outfits that won’t leave me looking like a rumpled mess.

Of course, hiring a stylist isn’t cheap. It becomes economical if, like me, you plan to not shop again for another year. It can also be a good idea if you need to purchase a lot of clothes in a short amount of time — for instance, if you’ve just landed a job with a different dress code, or have lost a ton of weight.

But you can also get a similar result for less money, too. Some department stores offer personal shopping services for free if you then purchase a certain amount of clothes from that department store. An even easier approach? Choose a boutique store with a style you like (Ann Taylor, Banana Republic), and then buy outfits straight off the mannequin. Down to the handbag or tie. Someone who works in the fashion industry styled those mannequins, and that’s a free way to take advantage of his/her expertise.

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