I was sprinting through Back Bay last Tuesday, trying to make it from a client meeting at State Street to drinks with my Harvard Business School alumni group, when it hit me – I was wearing the perfect example of my shopping philosophy without even thinking about it. Target jeans ($24.99), a white Everlane tee ($18), and my beloved Max Mara camel coat that I saved up for over eight months. Oh, and the Bottega Veneta mini Jodie that nearly gave me a panic attack when I bought it but has since become my most-worn bag.
This is how I approach fashion now, and honestly? It’s the only way that makes sense for someone like me who needs to look polished for corporate America but also wants to, you know, have money left over for things like rent and my 401k contributions.
I call it the “finance professional meets fashion editor” approach, though I guess it’s more commonly known as high-low dressing. But here’s what I’ve learned after years of trial and error (and some truly regrettable purchases that I try not to think about): the key isn’t just mixing expensive and cheap pieces randomly. There’s actually a strategy to it that can make you look like you have way more disposable income than you actually do.
The whole thing started when I was a fresh MBA working at a smaller firm in Boston, making decent money but not “buy a new designer outfit every week” money. I remember walking into my first big client presentation wearing a full Ann Taylor suit – you know the one, that navy blazer and matching pants that every professional woman owns – and feeling completely invisible. Not professional invisible, which would’ve been fine. More like “beige wallpaper at a doctor’s office” invisible.
My mentor Sarah, who’s now a managing director and someone I still try to emulate, pulled me aside afterward. “You need at least one thing that makes people remember you,” she said. “Doesn’t have to be flashy, just… something.” She was wearing what looked like a simple black dress with a structured blazer, but something about her always looked more put-together than the rest of us. Turns out the blazer was vintage Armani that she’d found at a consignment shop, paired with a $40 dress from Banana Republic Factory.
That conversation changed everything. I started paying attention to which pieces actually made an impact and which ones were just… there. And what I discovered was pretty interesting – people notice the “architecture” of your outfit way more than the “filler.” The coat that creates your silhouette. The bag that anchors everything. The shoes that either elevate or deflate the whole look. The blazer that makes you look like you know what you’re doing.
Everything else? The basic tees, simple sweaters, straight-leg jeans? Honestly, no one can tell if you spent $15 or $150 on those as long as they fit well and aren’t falling apart.
My first real investment piece was a black Theory blazer that cost $495 – which felt absolutely insane at the time. I actually called my mom to talk me out of it, but she said something that stuck: “If you wear it twice a week for two years, that’s like $2.50 per wear.” The math made sense, even if the upfront cost made me nauseous.
That blazer transformed my entire wardrobe overnight. Suddenly my cheap white button-downs looked crisp and intentional. My basic black pants looked sleek instead of sad. I wore it to client meetings, networking events, even weekend brunches thrown over jeans and a tee. It was like having a secret weapon that elevated everything else I owned.
The real test came during a conference in New York where I was representing our firm at some pretty high-level meetings. I wore the blazer over a $12 Target tee, paired with pants from J.Crew Factory and my one pair of good heels. Afterward, someone from Goldman asked where I got my “gorgeous suit.” I just smiled and said “thanks” – no need to explain that three-quarters of the outfit cost less than her lunch probably did.
That’s when I formalized my strategy: spend serious money on the pieces that create structure and make a statement, then fill in with well-chosen basics that won’t break the bank. It’s not about being cheap – it’s about being strategic.
Now, after years of refining this approach (and making some expensive mistakes along the way), my wardrobe operates on a two-tier system. Tier one includes maybe six investment pieces that I saved for, researched obsessively, and take extremely good care of: the Max Mara coat I mentioned, my Bottega bag, a Saint Laurent blazer I found at a sample sale, a pair of Louboutin pumps that have survived three years of Boston winters somehow, a Rolex my parents helped me buy for my 30th birthday, and a vintage Burberry trench I scored on The RealReal.
Everything else is tier two – the supporting cast that makes the stars shine. My white tees are from Everlane or sometimes Target if I’m being honest. My jeans are mostly Madewell or vintage Levi’s. My basic sweaters come from Uniqlo or Sezane when they’re having a sale. My workout clothes are exclusively from Target because I refuse to spend real money on clothes I’m just going to sweat in.
The beautiful thing about this system is that it scales with your budget. When I was making less, my “investment pieces” were contemporary brands like Theory and Vince, purchased on deep discount. My basics came from places like H&M and Zara. As my salary increased, the ceiling for investment pieces got higher while the floor for basics got a little more comfortable too – upgrading to more sustainable options that still don’t require taking out a loan.
I tested this theory at a work dinner last month where we were entertaining some pretty important clients. I was wearing my Saint Laurent blazer over a $18 Target tee, with jeans from Madewell and my good heels. Over cocktails, one of the clients complimented my “beautiful jacket” and another mentioned how “effortlessly chic” my whole look was. No one asked about price tags because they didn’t need to – the overall impression was what mattered.
Here’s what I’ve learned about making this approach actually work: First, be brutally honest about what deserves investment and what doesn’t. Ask yourself – will quality make a visible difference? Will this piece get heavy wear? Does it create the foundation of my look or just fill in the gaps? For me, outerwear almost always justifies spending more because it’s literally the first and last thing people see. Same with bags and shoes – they take a beating and cheap versions often look obviously cheap.
But basic tees? Simple sweaters? Even jeans, honestly? The difference between a $30 version and a $300 version often isn’t visible to anyone but you. And sometimes the cheaper version actually works better – I’ve found that inexpensive cotton tees often fit better and move more naturally than overpriced designer ones that are trying too hard to be special.
Second, when you do decide to invest, save up for exactly what you want rather than settling for the “almost” version. I wasted so much money on intermediate bags before my Bottega – each one costing $200-400 and none of them scratching the itch I was trying to scratch. If I’d just saved that money toward the real thing, I would’ve gotten there faster and been happier with the result.
Third, take care of your investment pieces like they’re the precious objects they are, while being realistic about everything else. My Max Mara coat gets professionally cleaned and stored properly. My good bag never touches the floor of a restaurant or gets tossed around carelessly. Meanwhile, my Target tees go straight in the washing machine and get replaced when they start looking tired. This two-tier care system keeps the special things special while letting you actually live your life.
The question I get most often is whether people “find out” about the cheaper pieces and judge me for them. But honestly? No one in corporate America is checking the labels on your white tee shirt. And even in fashion-forward industries, the most respected people are usually the ones with the best eye for mixing, not the biggest clothing budgets.
Just last week I was at a networking event chatting with a senior partner at a major law firm who’s known for always looking impeccable. She was admiring my shoes (the Louboutins) and mentioned that she has the same Target jeans I was wearing in three different colors. “Why spend more when these fit perfectly?” she said. If that’s not validation of the high-low approach, I don’t know what is.
The other thing I’ve realized is that this strategy actually makes getting dressed easier, not harder. When you have a few really strong pieces that you love and trust, building outfits becomes more like playing with a reliable formula than starting from scratch every morning. My blazer works with basically everything. My coat makes any outfit look intentional. My good bag elevates even the most basic jeans-and-tee combination.
So if you’re debating whether to spend half your paycheck on that perfect coat or investment bag, here’s my advice: do it, but pair it with smart basics that don’t drain your bank account. Because at the end of the day, looking put-together isn’t about having an unlimited budget – it’s about knowing where to spend the budget you have. And trust me, no one needs to know that you’re shopping at both Target and Bergdorf’s. They just need to think you know exactly what you’re doing.
By day, Jasmine works in finance. By night, she writes about making corporate fashion actually interesting. Her Boston wardrobe proves office-appropriate doesn’t have to mean boring, and that investment dressing can be both powerful and personal.
