“We’re gonna go Macklemore on you and talk about how to build a great looking — and often even high quality — wardrobe without emptying your wallet.”

Financial Friday: Ballin’ on a Budget

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For today’s Financial Fridays episode we’re going to go Macklemore on you and talk about how to build a great looking — and often even high quality — wardrobe without emptying your wallet. I do want to mention that it’s possible some of these ideas may not translate perfectly to women’s style, but I think a lot of the underlying ideas should be applicable across the board.


One potentially obvious place to start would be thrift stores. Thrift stores can be a little challenging to figure out; high income areas may be more likely to carry luxury brands but they are also more likely to get snatched up by label-aware shoppers. At the same time, at larger chains like Goodwill and Salvation Army, clothes will occasionally move around from city to city depending on the systems in place for those particular stores. I make it a point to visit nearly any intriguing thrift or vintage store in any city I live or visit, and in my experience the highest hit rate for great finds have occurred at non-chain or small-chain stores with very high volume. Of course, certain geographies and specific stores may differ, so it’s valuable to do a little learning on good brands and labels before setting out to hop thrift stores.


As I write out the ideas for this episode, I’m wearing a grey peacoat style coat that I bought at a thrift store for $25. I noticed the coat first because it looked nice, of course, but secondly I noticed that the brand was INC, a Macy’s endemic brand that makes high quality non-luxury clothing in either timeless or borderline offensive styles. I knew that INC coats ran about $100-200 from previous trips to Macy’s stores, and a quick google search at the thrift store suggested that the coats most similar to the one I found were around $125 new. In this case, I’d found a timelessly wearable coat in my size with very minimal wear and tear beyond some scuffing of the metal buttons. In the same trip I also found two slim fit button downs from J Crew and Banana Republic, both considered high quality but sub-luxury labels, for about $3-4 per shirt. The shirts had no noticeable inconsistencies or damage and fit well. Purchased new, they’d probably be closer to $30-60 each depending on whether they were bought on a sale or at full retail.


That all having been said, the most key things to look out for when buying upper body outerwear at a thrift store are fit and quality, and this absolutely holds for men or women. You’re unlikely to excitedly wear cheaper labels like Mossimo or Forever 21, the clothes are likely to prove less durable, and though both labels are perfectly respectable, their clothes can nearly always be bought brand new at a department store at a very affordable price, so your overall savings on thrifted clothes from cheaper labels is unlikely to justify buying used. By contrast, I’d consider a few extra bucks spent on a better fit and label to be a superior thrift store find.


In my experience, accessories and footwear worth buying can be much harder to come by, as it seems people tend to wear shoes until they are all but falling apart. It may seem tempting to buy a nice brand like Nike or Alden for peanuts, but if the upper is torn and the sole is coming apart, it may not be a worthwhile buy. Similarly, accessories are somewhat niche, so quality accessories are rarely owned by people unaware enough to donate them. That said, I always check out watches, as I possess a far above average knowledge of watch brands, authenticity, and value, and every few months you see a story online of someone paying $8 for an Omega worth $3000. Odds are, these things usually get donated when someone older passes away the family donates a lot of their belongings without knowledge of their value. This has yet to pan out for me, but for those of you out there with a particularly thorough knowledge of something others don’t, such as shoes, watches, purses, necklaces, suits, musical instruments, and electronics, being thorough about exploring thrift stores will probably eventually pay off for you.


Pants are an area I’ve not personally had much success, probably because I have relatively short, stocky legs and I’m fairly particular about pants that fit very slim but never skinny. However, I have noticed at most thrift stores that women’s denim selections are often several times more extensive than men’s, and with a lot of women’s pants following a similar formula of skinny with small pockets, and with women tending to cluster at more similar sizes, I would be willing to bet a more or less average height and weight woman will have somewhat frequent success at finding great labels in their size. I have more than just once talked to women in my area who share with pride that their True Religion jeans and Vans canvas shoes came from the EcoThrift store down the street at about $10-20 a piece.


I mentioned earlier the importance of fit. This can’t be stressed enough when it comes to style – it will not matter any whether you’re wearing a $5 shirt from a thrift store or a $250 shirt from a Neiman Marcus, if it fits poorly for your body, style, and context, it will look bad. A vast majority of people don’t really know much about style rules or quality brands, so if you’re looking to make a good impression and get compliments, it is paramount that the fit is right. Probably the most complimented article of clothing I own is a slim fit burgundy sweater I bought from Bonobos for about $30 including tax and shipping by buying during a sale, and I chalk it up to buying a high quality sweater in a nice, safe color and layering it with a coat in colder weather or on top of a very colorful button-down so the collar popping out provides a very minute accent. So therein lie the next two big rules of ballin on a budget: buy or tailor for fit, and buy on sale.


Many, but not all, articles of clothing can be tailored to fit you perfectly at relatively low cost. This can prove to be a great way to take advantage of a great deal at a thrift store or during a sale when what’s available doesn’t fit perfectly. This is especially true for formal wear regardless of gender: appearance is absolutely not everything, but you should not be caught dead going to an interview, business meeting, or presentation in ill-fitting clothes. Women with enormous shoulder pads and men with coat sleeves to their fingernails has seldom ever in history been considered the prevailing example of style. If you find a shirt you love on sale but it doesn’t fit perfectly, or a high quality suit at the thrift store is just an inch too big everywhere, odds are you can get the clothing tailored affordably and turn a baggy button down into a magazine-ready statement piece. Fit and material quality are the only things anyone will recognize as “nice,” so in general you should aim there. Nobody will really know or even care if your shirt is from Gap or Yves Saint Laurent, if it looks nice and fits you well, you’ll come off as someone who knows what they’re doing when they shop and dress themselves. The reality is that dressing terribly is going to make a bad impression with just about anyone, while dressing reasonably will rarely go unnoticed and dressing well will nearly always be noticed and thus make a strong impression. Again, appearance is of course not everything, but it will be the first thing anyone you interact with will judge you on. Whether you think so or not, you do this too, so you might as well dress nicely as there is nearly no scenario where it will hurt to do so.


Buying on sales is another powerful way to expand your wardrobe very quickly without selling off an arm and a leg. It can be very valuable for you to learn when sales events occur at your favorite brands and department stores so that you can make higher volume wardrobe expansions in concentrated bursts. I recommend doing this even if it means you’ll spend a decent sum of money at once, because at the end of the year you’ll likely save hundreds of dollars on great outfits compared to buying them at or close to full retail throughout the year. Nordstrom’s best sales event, for example, is not during the holidays, but rather during their anniversary event during the summer. Considerable markdowns occur across most brands, so this can be a brilliant time to buy luxury quality clothes at comparatively low prices. Of course, this begins to move away from frugality and budget buying, but if for example you work in an environment where a great pair of shoes or a quality suit is important, it can be a good investment to save up and prepare to spend most of your clothing budget at once during such an event. Last year I bought a pair of Allen Edmonds shoes and paid less for the shoes, horsehair brush, two shoe trees, and polish than the shoes would normally cost any other time of year. They weren’t a cheap or frugal buy, but months later I cannot put the shoes on without a smile, and they always make a strong impression when I’m meeting with a client or heading into an interview. Not only that but high quality shoes that are well cared for are known to last a decade before needing repair, and for a fraction of the original cost can be resoled, conditioned, polished, and replaced by the company to return them to near new condition. I’ve seen pictures of 40 year old luxury shoes and boots that have cost the owner about $500 in that time — even from a frugality perspective. you’d be far better off paying $500 for a pair of durable, great looking shoes than you would replacing cheap shoes every year or two for the rest of your life.


Aside from that particular example, Macy’s, Gap, and other stores tend to have sales running constantly, but many are something of a ruse. I highly recommend following or subscribing to an online forum such as the frugalmalefashion subreddit on reddit.com, as contributors at those communities are very tapped into whether retailers are hiking prices up then calling something a sale when in reality the prices are just marked down to what they’ve been all year long. More real sales tend to occur around the holidays and at the ends of seasons when previous season’s styles are being phased out for new lines – Macy’s has great doorbusters around Black Friday and Cyber Monday where typically you can pick up good-but-not-great quality shoes and outerwear at legitimately heavily marked down prices. As I write this, I’m wearing a pair of Kenneth Cole Unlisted boots that I bought during such a sale for $24.99 with free shipping. They retail at $75 normally and in reality they are average quality boots, but they are comfortable and look nice, and I don’t have to care at all about scuffing them or wearing them in the rain. Online forums are also clued into sales put on by online only retailers and smaller independent brands, which have a higher tendency to go out of business and thus liquidate their inventory at aggressively low prices. This past holiday season I bought pair of jogger sweats, a tank top, and a light jacket that I love, all for under $30 with tax and shipping. The first day I wore the jacket into work I must have gotten 5 or 6 compliments on it and some people were in disbelief that I paid less than $10 for it.


So we’ve covered thrift stores, tailoring, and sales events. The last tip to ballin on a budget is to buy used. Sites like ebay, Grailed, and niche fashion forums for makeup, fragrances, watches, jewelry, and shoes frequently feature high quality clothing in great condition that people are selling due to a change in weight, a change in style, a change in occupation, a change of heart etc. and for you this can mean paying 50% less than retail for something that will last you your entire life. This does take a little more knowledge of what to look for, which is why I mention it last; without relatively high awareness of how something will fit you and what brands and materials you’re looking for, it can prove a little challenging to take full advantage of this tactic, but for those of you looking for something normally out of your budget, this can be an effective way to work something into your budget with minimal sacrifice to condition.


All right everyone, thanks for reading and as always please share your thoughts, your praise, your criticism, it all serves to make the show better. Follow us on Instagram! @thewealthyhealthy