It takes patience, but try Sierra Trading Post. In particular, check out the “classics” grouping. Not everything is super cheap, but most things are high quality, and some things definitely are super cheap. They carry many designer labels in last year’s or last season’s colors or styles. I generally avoid seconds and get overstocks, and even so find some ridiculous bargains.

They’re generally very good about returns (as long as you don’t buy a ton of stuff and return the vast majority of it…keep you return rate below 50% and they won’t hassle you about it). I’ve never had any kind of customer service issue from them. They are, apparently, run by evangelical Christians, but they don’t try to convert you or anything; I occasionally am a little surprised to see bible verses on the site but it’s never appeared to be over the top or proselytizing (and some people no doubt actively prefer to shop at an organization that is owned by Christians).

You can almost always find free shipping and other percentage-off coupons by using Retail Me Not or similar sites.

Once you’ve made your list of needs, organize in order of priority and just check the site occasionally. You’ll have to search through a lot – their inventory is staggering – but it pays off. You can use search terms (like “wool” or “cashmere” or “Schoeller”…some of my favorites) to narrow down the field a little. They often carry specific brands a lot, so if you find a brand you like you can usually get your size dialed in pretty well. And shoppers there are active commenters, particularly about fit.

Good luck, J.D.! And congratulations on your amazing weight loss…I read GFS, too, and have watched your progress with just a little bit of envy.

Everybody has sales. I get short sleeve polos at Kohls, they last a couple of years but are only about $10. Certain things like that I’ll buy cheap, but not everything. Brooks Brothers has regular sales as well as corporate discounts.

One place I don’t skimp is shoes. A quality brand like Allen Edmonds will last years and can be recrafted and/or resoled.

Next, buy QUALITY!! I always went to Joseph A Banks. I have bought top of the line dress shirts and pants from them that have easily lasted 7-10 years. Take good care of them on both the wearing/cleaning ends and you will have very long lasting clothes.

I recently needed a dress shirt and pants at the last minute on our trip around the world. I bought cheap and couldn’t believe how quickly they fell apart – never again!

http://www.huffingtonpost.com/susan-gibbs/the-true-cost-of-cheap-ca_b_534551.html

I don’t know if you get “over the river” to the Assistance League store in Beaverton, but they always have quality clothing at very reasonable price.

Check it out, you will return home happy!!

I would love to get coffee if Well Suited works out. I am pretty sure you have email through the comments section. Good luck replacing the wardrobe.

Check it out.

Considering you live in Oregon (I assume rainy and cold winter), age (late30s, early 40s?) and that you want to start from scratch I recommend you the following:

1st know what kind of colours suit you, for example I look great in red and royal blue, good in navy, black or white and bad in grey, sand or brown. Get to know which colours you like better, which might not be the ones you like more or the ones you’re used to.

2nd Get to know what kind of clothes/style fit better to you (and as you’re looking in the long run will keep fitting to you in ten years)

3rd Get basic clothes mixing what you like and a classic stile that will not be old fashioned in ten years using the colours and style you’ve decided before. I recommed you the following, it’s a bit preppy and classic but you can make an idea and change what you like:

-2 classic jeans (Levis 501 like), one dark blue and another light blue.
-2 chinos that go well with the colours that better suit you
-3 knit sweaters in different colours that fit you, I prefer cotton because is not itchy and you can wash them in washing machines, but it’s up to you.
-3 oxford cloth shirts in different colours that fit you, plus your white dressing shirt.
- 2 classic polos (colours that fit you, one dark and another one light)
- 2 coats one classic (Burberry like) and another for (Columbia, The North Face like).
- Stuff you like or to compensate your needs and style, for example if you find it too classic buy t-shirts and a hoodie) and needs (if you do outdoor activities like canoeing or cycling buy the appropiate stuff, you might need a suit for some occassions, maybe a blazer, etc).

I don’t say those brands, I just say the style like.

With that you have for multiple uses (going out for dinner, give talks, garage sales, etc). Combine them never using the same colour in the shirt and the jumper.

About buying them I’ll buy at sales/outlets etc good quality/good brands the ones you can find. The rest buy them cheap. After that with time drop your cheaper clothes as they get old with ones you buy in sales/outlets of better quality. Give yourself a budget and use it.

Dressing well takes more time than money, when you know what fits you well you’ll need less time. Ask your wife, if your female/gay/fashionist friends give you unsolicited compliments you’re on the right track.

And a last thing, it doesn’t matter how little you paid for something, if it doesn’t fits you or you don’t look good with it. If yo’re using it more than staying at home or working in the garden you’ve wasted your money.

I would suggest devoting some time to it and trying on a LOT of different things. This is what I have done to rebuild my wardrobe at least 3 times in the past 5 years (once due to promotion, once while losing weight due to kid #1 and once while losing weight with kid #2).

The thing I like about thrift stores is that sometimes I end up trying on things that I wouldn’t in a regular store and really liking them.

I find high end items in my thrift store. I believe that is because it is in a wealthy area. The other thing I love about my thrift store is that they have shopping carts!

They carry a lot of REI, Orvis and other higher end brands.

That being said, I have built a decent collection of work-appropriate shirts and pants by finding the brand/label that fits me well, and then hitting up their sales. Sure, I probably wouldn’t have bought that pink floral button-down tunic blouse if I’d seen it on the rack in a store, but when it was on sale for $20 from my favorite catalog vendor, I bought it and have worn it several times a month for the past four years. For me, work clothes serve a purpose and don’t have to reflect my personality or fashion preferences. If you can buy quality goods on sale and don’t mind that you’re getting the least popular options, then you’ll get a lot of wear for a little cash.

1) I would start rebuilding by focusing on a color palette. It is winter, so think all grays, browns/tans and pumpkin or squash for a pop of color. Why color? Because it keeps you focused at any store, be it thrift or Target. You get more outfits for less money as things mix-and-match better. And find the RIGHT shades — some colors (like what they offer at Old Navy) are “off” or obnoxiously too bright.

2) Each season, you rotate out clothes for new colors/clothes. That means you put them in bags and hide them. And then when you crack them out again next season, it’s like having bought a whole new wardrobe.

3) Lay down the money for better shoes, belts, shades and jeans, as people tend to notice these items first. If you don’t like designer jeans, get some classic Levis. The best of both worlds (comfort and never-ending style).

4) And the rule of scarves works for men, too, JD. A manly winter one will re-freshen up an outfit.

5) Always pay the money for something you always wear, like those REI shirts. Having 3 of those is better than having 9 of something else that equals the same amount of money, sans the dressing confusion. If you like what you wear, you’ll save time in the morning!

If anyone knows a good place to buy plain white under-shirts that don’t stretch out in the neck or shrink, let me know. I’ve given up on Hanes & FOTL.

As far as how to look nice, yes you can develop a uniform. Look at Steve Jobs or Michael Kors for instance. http://www.thegeekery.biz/?p=51 http://4.bp.blogspot.com/_gwZTIHwSxdU/SPUXuJyo1EI/AAAAAAAABI0/HFmIIXtWP-Q/s400/michael+kors.jpg

They wear the exact same thing every time. Personally, I find it boring. I think you’re better off developing your personal sense of style and then building on that. For inspiration on breaking out of your comfort zone, check out the Sartorialist. http://thesartorialist.blogspot.com/

I am a 26 year old tom boy, my closet is dominated by jeans and t-shirts. Very little in the way of business casual clothing. I have been on unemployment most this past year so I didn’t have a lot to flesh out a weekly work wardrobe.

I went Black Friday shopping. Picked up a good comfortable pair of shoes usually $110 for $70 also I picked up some nice sweaters for almost 50% off usual price.

Also I subscribe to the Consumerist blog. Every morning they have a “morning deals” post. The week the job was offered to me there was a 30% off entire purchase at Old Navy coupon mentioned in the morning deals post. I used this to get some khakis.

I’ve read your blog for about a year now and most of my friends would laugh to know that the first time I’m leaving a comment has to do with shopping for clothes. Clothing on a budget is my forte. Expensive taste on a budget is my life mission. Fashion is always important to me.

So I am one of those people who WILL pay for a $90 sweater…quality is really that important to me. Let me explain. I love Target. And, I love J Crew. Places like J Crew that make quality clothing will last you so much longer than other stores like Target, and even GAP, Banana Republic (depending on the item) and Old Navy. With that said, I’ll buy supplementary clothing from those places, meaning: If I’m unsure if it will be in style next year, I won’t buy the expensive version. Or if it is something like a scarf or socks or a tshirt, I will buy it. But I pay for quality for staple items. Why? Because it lasts. I have clothing from J Crew that has stayed with me from college (I graduated in 2002). I do not own a thing from 2002 that is from any other store other than a wool coat from GAP that the lining is just now ripping out of the insides. Technically it’s from 2003 but I’m surprised the coat has lasted this long. A pair of dress pants from JCrew cost $150 but they lasted me for 4.5 years. No pant from a cheaper store will last me that long. And, yes. I promise I don’t work for JCrew.

Here are my bullet point thoughts on how I purchase nice clothing items.

-I rarely pay for it full price but if it’s a good item, it’s worth it. Always.

-Buy your basics in quality. It just makes sense. Jeans, coats, shoes…not only do you look nicer but it’s fiscally responsible. For me, there are some things that just don’t last from season to season no matter what the quality. So I’ve learned over the years that white tshirts, most winter sweaters and pretty much any knit clothing will need to be replaced after 1-2 seasons for me just because they break down, stain or shrink faster with me. Don’t know why but they do. So I don’t pay a lot for those unless it’s really on sale. You’ll have things like that where you’ll learn they aren’t investment pieces for you like they are for others so you’ll think twice before you buy. That only comes with time.

-Since I’m love fashion, I will notice quality pretty quickly on others and have an appreciation for well tailored clothing. Quality fits better. One trick I have for myself is that I will buy one really “expensive/quality” item and then offset it with a not so expensive item. For instance I will buy a pair of designer jeans on sale that last for a couple of years…then I will buy a tshirt from Target. Adding quality with lesser quality still makes your outfit look good. (Not sure if you’re concerned with that but it’s my trick to always looking great).

-I’m sure you know this but ALWAYS ask about a sale. Sales people will sometimes divulge an upcoming sale, especially if you shop there often. Ask. Ask. Ask. Student discount, loyalty club discount (not credit cards), military discount, first time buyer discount. “Are you having a sale in the next couple of weeks?” I ask it often. Once I had a store hold a dress for a week for me because they were having a sale for 20% off that weekend. A lot of places have sales going on and don’t tell you till you get to the register.

-Some stores will waive shipping if you place the phone order in the store (JCrew does this as a standard practice). If not ask. Always ask.

-Buying quality can pay off if it shrinks, tears or just plain doesn’t work out. Norstrom, JCrew, Anthropologie, REI (just to name a few) will take back an item without a receipt at ANY TIME if you are unsatisfied. I wore a pair of KEEN shoes in Hawaii in July that I bought from Nordstrom just for that trip and hated them because my heel kept pushing back to the rim of the sandal, thus making my hiking miserable. Normally I love the brand so I was surprised it happened. Nordstrom took them back (dirt and all) just because I said they did not fit well. JCrew took back a button down after it shrank in the wash and Anthropologie took back a really expensive pair of jeans after they tore 6 months later. Just keep your receipts.

-This is pretty well known across the board but buy clothing items after they go on sale at the end of the season. I’m actually finding that because most stores put fall clothing out in August/July, it starts going on sale by October/November (sometimes even in September) and certainly by the week or two after Christmas it’s discounted significantly. It’s still cold outside during those times so technically I’m not having to buy a coat when it’s still warm outside and then wait all year to wear it. Start looking for sale items mid-season.

-Other tricks I use are to bookmark items that I really like and want to buy and then go back to them online to see when they go on sale. Also, if you order online always google “(name of store) online coupons” and see what happens. I almost always save on something.

-Finally, because fashion is so important to me for many reasons, I post a lot of inspiration pictures of outfits that I really like torn out of catalogues on my walls. Having the reminders up lets me keep an eye out for the clothes when they on sale but it also help me keep the “eye on the prize” so I don’ waste my money on frivolous purchases I won’t want later. (That’s also a financial trick I do for myself as well. Fashion is that important to me so I’ll strive to make a way to buy something that’s out of my budget when it goes on sale, or just save for it or make it work somehow. Keeping pages up on my walls near my dresser also gives me inspiration to make my closet work for me…often I can get a look with what I already have.)

One man’s comic book collection is another woman’s designer jeans collection.

I really like what Micah Smith said about clothing being an investment portfolio. So true. Balance it out across the board but put your money wear it counts. If a $45 shirt from REI lasted you for that long, axe the guilt and appreciate a well made purchase.

My consultant shops with me (she charges $50/hour but is unbelievably efficient), has cleared the junk out of my wardrobe, does needed alterations, and sews from scratch to a couture standard. She is worth every penny I pay. In addition, I have learned from her how to shop more efficiently. An example- I have never owned a pair of blue jeans I actually liked-I loathe jeans shopping. We went out about 3 weeks ago to buy jeans. She made me try on at least 35 pairs (I wd never have had the patience if I had gone alone), and I returned with 4 pairs of perfectly fitting jeans in different styles (straight/boot cut/skinny) and an understanding of what brand fits my shape (Tommy Hilfiger). 2 pairs didnt need hemming, 2 did. She did the hemming in time for a trip deadline. She brings any coupons and knows where the sales are, what inventory stores carry, and the best times/days/seasons to shop. When I add it up, with discounts, I am probably paying as much as I would have done if I shopped alone, but I like my clothes MUCH more, THEY FIT, and my wardrobe works together better as a whole. She works around my budget. I can now buy stuff myself to fill the gaps, though I usually ask her what she thinks afterwards.

My particular challenge is that I need accessories (shoes, bags, jewellery) that work with both Western and Indian clothes-she has been very helpful in this regard and I might take her sari shopping some time.

Stylists for men exist, if you want to go that route.

I NEVER EVER shop at thrift stores-too slow and time consuming not to speak of the junk you need to weed through-it is simply not efficient if you are time stressed, and there is a reason the stuff is cheap.

My consultant told me I lack accessories, so I now shop for classic basics and buy more accessories-it really makes dressing much more fun than it was! I prefer to buy fewer better quality items, so I dont mind paying full price. Even with alterations, they are a better investment.

I rarely have the patience for Ross/TJ Maxx and while I’ll buy polos/tees/boxers at places like Old Navy or Target I think their pants and dress shirts are usually pretty chintzy looking. I always feel like I’m getting scammed at outlets. I do, as many others noted above, often find great deals on dressier pants/shirts/sweaters on the clearance racks at Banana Republic.

Icebreakers definitely rock. Nthing Sierra Trading Post for deals there. You can also brave an REI garage sale if you’re up for that sort of thing.