Your first real job comes with a lot of surprises: the 9 a.m. stand-up, the 401(k) paperwork, and the sudden realization that your college collection of hoodies and frayed chinos isn’t going to cut it. You need to look professional, but you also need to pay rent, maybe tackle a student loan, and still afford the occasional happy hour that makes the office grind tolerable. The good news? You don’t need to drop two months’ pay on a full designer lineup to look polished and put-together. With a little strategic shopping, you can build a starter wardrobe that punches way above its weight class. The trick is knowing what to buy new, what to buy used, and when to pounce on a sale.

Start with the pieces that do the heavy lifting. For most office environments, that means a navy blazer, a couple of tailored button-downs, a pair of dark dress trousers, and shoes that don’t scream “borrowed from my dad’s attic.” These four items will carry you through interviews, client meetings, and casual Fridays if you swap in a good pair of jeans. Rather than spreading your budget thin across ten cheaply made garments, concentrate your cash on the items that get the most wear and face the most scrutiny. A sharp wool-blend blazer at a mid-range price will look twice as expensive as a bargain-bin polyester jacket, because fabric and construction are what people notice first. Suits and jackets are also the easiest pieces to find at steep discounts, especially if you clear out the seasonal end-of-line racks.

The retail calendar is your best friend. Most department stores mark down men’s and women’s suiting sharply after January and again in late July, clearing space for new seasons. Sign up for email alerts from J.Crew, Banana Republic, and Nordstrom Rack, but don’t stop there. Off-price retailers like TJ Maxx and Marshalls get regular shipments of high-quality brands, and their inventory is unpredictable enough that you should stop in every couple of weeks. Hit them mid-week, when shelves are freshly stocked and the weekend scrum hasn’t torn through yet. For shoes, look for last season’s colorways on sites like Zappos and 6pm.com; a classic oxford or a leather loafer in brown or black rarely changes style, so you’re just paying less for the exact same craftsmanship.

Shirts and trousers are where you can afford to be a bit more flexible. A white oxford shirt, for example, is so ubiquitous that thrift stores are often overwhelmed with them, many barely worn from the guy who quit banking after eighteen months. Same goes for solid-color dress shirts. Check the neck and collar for fraying, hold it up to the light to see if the fabric is worn thin, and inspect the underarms for lingering discoloration. You can find genuine Brooks Brothers and Charles Tyrwhitt shirts for five or six dollars this way. Trousers are trickier because fit varies wildly, but if you know your waist and inseam, you can do well. Avoid anything that would need extensive tailoring, since that extra twenty dollars per garment erases your savings. Learn to do basic hemming yourself instead. A simple hand-stitch or even hem tape works fine for the first few months, and sewing machine prices at garage sales are absurdly low if you want to level up.

Don’t overlook outlet centers, but walk in with healthy skepticism. Factory outlets often carry lower-quality versions of the mainline brand, with thinner fabric and cheaper buttons. Stick to outlet stores that actually receive overstock from the main label, like Brooks Brothers or J.Crew, where the discount reflects real markdowns. Better yet, browse their clearance section online during major holiday weekends. Memorial Day, Labor Day, and Black Friday are prime hunting grounds for steep price cuts, and stacking cash-back portals like Rakuten can shave another few percent off your total. Set a ceiling for each piece before you start shopping, and refuse to exceed it. When you see a quality blazer originally priced at two hundred dollars marked down to seventy, that’s a win. When you see a “sale” that brings a ninety-dollar shirt down to sixty-five, just keep walking.

Another underappreciated resource is tailoring. A five-dollar thrift store blazer that’s two sizes too big can become a fitted, custom-looking jacket for a thirty-dollar alterations bill. Shoulder fits are hard to fix, but waist suppression, sleeve shortening, and taking in the sides are all straightforward for a decent tailor. Look for blazers with structured shoulders that already sit correctly on you, then let the tailor do the rest. The same logic applies to trousers that are too long but otherwise fit your waist and hips. Your local dry cleaner often does alterations at a fair price, and independent tailors listed on Yelp are worth the trip. Never underestimate how much a well-placed dart or two changes the whole silhouette.

Finally, think in terms of rotations and layers. Three pairs of trousers, four or five shirts, two jackets, and a single pair of quality shoes can produce dozens of distinct outfits, especially if you keep everything in a narrow, complementary color range. Navy, gray, white, and light blue all mix and match endlessly. Add a couple of ties or silk scarves if you’re feeling fancy, but keep them neutral so they don’t go stale quickly. When a shirt starts to show collar wear or a pair of pants loses its crease, replace it immediately with a better version of the same thing from your discount hunting. Building this wardrobe takes a few weeks of patience, but once the foundation is set, you’ll stay sharp for years without ever paying full price.