If you were building your wardrobe from scratch, how would you do it? Would you prioritize quality? Would you emphasize cost? Or is there some happy balance between the two? That’s what GRS reader author J.D. wants to know. He writes:

I’m a 40-something guy who’s lost 40-something pounds over the past year. This is a good thing. But now my old clothes don’t fit. As a frugal fellow, this creates something of a dilemma. How do I re-build my wardrobe while keeping an eye on costs?

For most of my adult life, I’ve dressed in what I’d call Modern Slob. Or maybe Geek Casual. My wardrobe comprised jeans, t-shirts, and sweatshirts, most of which were purchased at Costco and local thrift stores.

Now that I’m slimmer, I’m more interested in dressing well. That is, I want to look nice, and not like I don’t give a hoot. I don’t need to buy a suit, but I’d like to learn how to buy affordable clothing in classic fashions. I don’t know where to start.

First, I’ll stop referring to myself in third person. (It’s like a bad Seinfeld episode or something.) Next, I’ll elaborate on my concerns.

I really do have something of a wardrobe crisis. Downstairs in the living room, I have a pile of clothes that no longer fit. I’m gradually giving these away to friends and family (and will donate the rest to charity), but meanwhile there’s little left to wear. I don’t need to rebuild my wardrobe to the size it was before my wardrobe project, but I do want to have some essentials on hand. Right now, I have no dress shirts that fit. And no dress pants. And no turtlenecks. And no jeans.

I could go on a shopping spree at the local mall, I suppose, but that’s so not me (and on so many levels). I’ve tried to buy some new clothes at Costco, but I don’t like the fit and fashions they offer right now. That leaves me with the thrift stores, but these are an imperfect solution. I’m truly puzzled about how to build a wardrobe on a budget.

Affordable fashion?
Lately, out of curiosity, I’ve been reading magazines like GQ and Esquire. I haven’t done this in 20 years. (And once this spell passes, it’ll probably be another 20 years before I pick them up again.) While entertaining, there are a couple of problems with modern fashion mags:

  • I have zero interest in buying “fashionable” clothing. I abhor the idea of owning something that’s hip today but which may be unwearable five years from now. I’m drawn to what Alan Flusser calls “permanent fashion“. (And the casual end of that.)
  • I’m not willing to pay big bucks for clothes. I cringe when I read things like: “Yes, you could buy a cashmere sweater for $90, but why would you? Top quality costs ten times as much, but it’s worth it.” Not to me, it isn’t. No sweater is worth $900. Remember, I’m accustomed to buying sweaters for $9 at Goodwill.

Surely there’s a balance to be had. There must be fine clothes available at reasonable prices, especially for folks like me who don’t give a whit about labels. I just want quality. (And although it pains my frugal nature, I’m willing to admit that maybe paying a little more for quality is worth it.)

Does quality trump cost?
For example, I recently bought an Icebreaker merino wool t-shirt on sale at REI for $45. I felt guilty about this for days (because it’s three times what I’d usually spend on a t-shirt), but then I wore it during our trip to Europe. I loved it. The shirt felt great, but best of all, it never stank — even after I wore it for a week straight. (No joke.) If that t-shirt holds up to wear, it’ll be worth $45 in my book, and I’ll no longer feel guilty about buying it.

But I’m not willing to spend $45 each on a drawer full of t-shirts. That’s crazy, right? Plus, I’m not ready to rule out thrift stores. I can buy great stuff there for cheap. Just last week, for example, I went thrift-store shopping with Kris and her sister. I was giddy to find one of my favorite shirts — one that I’ve purged because it’s too large — in size medium. For five bucks. (Then I found two more from the same company that I picked up, too.) And just yesterday, I bought a nice-looking pair of name-brand corduroy pants for $6 at another thrift store.

If thrift stores are so great, why don’t I use them exclusively? Well, they’re a great way to supplement the clothes you already have, but it’s tough to use them to build a wardrobe from scratch. Their selection is…random. And there’s no co-ordination between styles.

Help me help myself
So, dear readers, I need your help. Tell me: How do you find affordable clothing? If you were building a wardrobe from scratch, where would you start? Is it feasible to do this just using thrift stores? Are you willing to pay more for quality? How much more?

Finally, can you recommend any websites about dressing well? (I’m especially interesting in learning how to dress well on a budget.) Or maybe I should forget about looking nice and just go back to being a modern slob!

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