How would you help someone acquire a new work wardrobe?

I have a relative, “Mike,” who, after a long period of underemployment, has finally gotten a decent job which starts in two weeks. The new position will require Mike to dress conservatively and attractively, which will be a problem given his current wardrobe. My cousin “Sandra” & I both want to help Mike out, but we’re at loggerheads as to how to do it.

One of us wants to go shopping FOR Mike–partly to make sure he gets high quality stuff at a good price, partly because he doesn’t have the best judgment when it comes to fabric and color, partly because presenting him with some new outfits would be a joyful surprise for him, and he’s been having an rough time of it for quite a while. The other of us thinks it would be better to just give some gift cards to Macy’s & Dillard’s, or even just the cash; the reasoning there is that the clothes (and particularly the shoes) are more likely to be comfortable and to Mike’s taste if he chooses them himself, and that the shopping will simply be more efficient that way (rather than involving multiple trips to the store if something happens not to fit well).

Thoughts, anyone?

The best option is to offer to go shopping with Mike. He picks out the things he likes (with some gentle guidance from you), and you pay. Someone offering to take me shopping and pay for it is just about the best gift you could possibly give me. Although I’m a woman, and this is more of a woman thing, I’ve also seen guys get pretty excited about a shopping trip where someone else is paying the bill, especially when it’s for something that he knows he needs.

If he’s the kind of guy who would accept and enjoy being taken out and fussed over while you pick the right suit, shirt, tie, shoes, socks combos, then that’s the best option. You can get the store to tailor things right on the spot.

Leaving him to his own devices with a gift card is just going to end up with him making more poor choices.

How about taking Mike out for a day of shopping? Lunch included. But then you can suggest the basics and help him with clothes that mix and match well, and be sure the clothes fit.

But “conservative and attractive” is pretty easy to achieve -three pairs of slacks (one blue, one black, one gray), five dress shirts, one good pair of shoes, and a jacket and some ties (if necessary).

It is nice of you to do this. I am going to have to ask for your Evil Card.

Regards,
Shodan

I am helping Mike for entirely selfish reasons. He’s my friend and I love him; therefore helping him makes me feel good. My evil credentials are not in jeopardy.

You have to take him shopping. Then you get the correct size and keep things (somewhat) within his comfort zone. Keep it happy and fun!

Those makeover shows provide ample evidence that, for people who are not accustomed to buying the proper clothing for themselves, sending them to the store with money (in whatever form) really doesn’t work. It creates too much stress and anxiety and indecision.

For me, all my work shirts are the same brand and size, and all my work pants are the same brand and size. So, figure out a style and brand and cut of pants that works and note the sizing. Do the same with shirts. It will make it easier in the future for him, it will narrow his choices and he will know just what to get.

I suppose it depends how much he wants to be involved.

If he hates shopping maybe get his measurements then someone better at this kind of thing could text him a photo of a few choices. He can pick or use the gift receipts to return it.

I think this isn’t the right way to go either, because if you buy things he might hate it and not wear it, and he has no one to blame but you guys.

Best suggestion is exactly what Shodan said. Let him pick his stuff out, get him the stuff mentioned (maybe 2 shoes, brown and black).

Department stores are gonna be your best friends because they always have some kind of good sale going on, Khol’s cash is good to

I disagree. Disinterested assistance is not the only, or even the most, virtuous kind of assistance.

I agree with all the suggestions to take him out for a day of shopping. If there are several people willing to contribute, maybe you could come up with a total amount to spend beforehand, but I think only one person (or at most two, who generally agree with each other on style matters) should go with him. You want to not only give him some fish but teach him to fish for himself next time.

[befuddled general zod]

Why do you keep saying such things, when you know I will kill you for it?

[/befuddled general zod]

Maybe. His taste isn’t THAT bad–just sometimes odd. I’m the cousin who’s opposed to just buying everything for him, because he’s a grown damn man and that’s kind of condescending. Also because I used to sell shoes and buying shoes for someone not present rarely ends well.

This is probably the best- point out to him that you’ve been at this employment thing for a while, and offer to give him a hand with the selection at least, and with the actual payment if he’ll let you.

The most important part won’t necessarily be the clothes you buy, but rather hopefully through the teachable moments you’ll have while convincing him NOT to buy some sort of suit that would look right on Craig Sager.

And “conservatively and attractively” may just mean not wearing basketball shorts and rude t-shirts with tennis shoes.

Nope. Has to be a suit & tie. And he’ll get judged (though nobody will comment to his face) on his shoes as well.

Take a day, tell him you or your wife need some xxxxx which can be found at real bargains at Thrift stores. Tell him if he comes along, your wife will help him pick out a few nice sets of great used clothes for work, but he will also help you find xxxxx. He’s doing you a favor, you are doing one back. (You gotta have some hobby or collection that would fit into xxxxx, right? Disney, Rabbit tsochas, Hummel, Yarn, golf, etc??)

You can get really nice clothes at a Goodwill or Salvation Army. And, what’s nice, they will either be next to new or look slightly worn, which means he wont look like he had to buy a whole new wardrobe for work.

A number of department stores offer personal shopping services. You call, tell them your size, your approximate budget, and what you need clothing for - they find selections that fit your criteria in the store. You spend a few hours trying things on and making selections. The service is usually free.

If it’s the type of job for which that might be appropriate, you may want to sign him up for that - offer to take him out for lunch or dinner afterwards.

I like this idea. I had a personal shopper at Nordstom and it was a good deal. She always did a much better job than I could making sure that everything I bought worked in several combinations. She was also awesome at knowing what was on sale and where the bargains were. I know it cost me less to have her pick out a few full outfits at a time as opposed to me piecemealing it.

My husband hates to shop and also swears by Nordstrom’s personal shoppers. They will actually stay within your budget.

Ah, suits.

Keep an eye on Jos. A Banks for their insane sales.

Take him shopping, keep it simple. Without being condescending, explain that in the office environment, it’s not good to get too original with your tastes, so keep it conservative.

If it’s suits, you can’t go wrong with blacks, greys and navy. Simple cut, avoid stripes.

Shirts, again keep it simple but you can allow him more leeway here to chose certain colours or designs as with Ties.

Shoes, don’t have to be expensive just look good.

3 suits, 8 shirts, 8 ties and a pair of shoes is a years wardrobe.

Does he require business dress, or just something to wear to a grunt job and not look like a bum? That would be an important difference in your approach. If all he needs is neat-looking jeans and a button shirt, what’s the problem? But if he needs a business suit, then somebody has to make sure he looks presentable.

We did something like this, for a close friend who’s father died. He didn’t own a suit, so we found a store that sells only mens clothing, explained to the salesman (it’s always a men working there, as far as I’ve seen), and asked for help. By being at a mens clothing store, we took out the whole “I am overwhelmed by the shopping mall” thing, keeping the stress down.

Mike can point out what he likes, the salesman will help find stuff that goes together well, and you can have veto rights, while at the same time not being the one steering Mike away from the awful stuff. Do let Mike have some say, especially when it comes to ties. But a half way decent salesman will be sure that you don’t end up with stripes and polka dots, in clashing colors. Don’t forget a belt and soxs, and even shoes if needed.

Mike gets to see what goes together, and why you need a brown belt with brown shoes, without having to try to figure out big department stores, where stuff can be scattered. Plus, all the attention can be kind of fun.