1. Commit time to scouring the sales. There’s going to be a lot of footwork involved, lots of frustration in which you try something on and it doesn’t fit just the way you want it to, and a fair number of days in which you go home empty-handed, but this is part of the hunt. (My mom has legitimately hung up on me when she’s found out I’m shopping because apparently I can’t keep a phone conversation while simultaneously, systematically taking a sale rack apart.)
2. Know which higher end stores offer the best deals.
You can find really great things tucked behind the triple-digit price tags, especially if you manage to find a sale wherein you take an extra 40% (or more!) off the sale price. (They exist, and they’re glorious. Intermix and J.Crew are my two favorites, and are pretty reliable in their markdowns. I once scored a Martin Margiela dress for $15 from the former.)
3. … and buy your staples there. The sale section is awesome because it also makes you really evaluate exactly how much of a “trend” piece something is – if it screams “last season” and you’re already put off from that, how much wear will you actually get out of it? Instead, it’s often best to stock up on jeans, tees, basic sweaters — things you know you’ll wear time and time again. Chances are good you’re buying something that’s higher quality, and you need that in your basics; they’ll withstand more wear, and you’ll save more in the long run because you’re not replacing them every season.
4. If you’re in the market for one piece, know when to buy it. It’s logical enough that stores are going to be more eager to move product they couldn’t sell with the changing of seasons, but in case you need a primer for really zoning in on a money purchase, there’s significant research as to when you can score the best deals on big ticket items.
5. If you haven’t already, set up Google alerts for sales. Style blogs are pretty good at sounding the alarm so their readers know where the bargains are, and using an alerts tool will send all of that info straight to your inbox as it happens. You can also use a fashion website aggregator like Shopstyle to let you know when something you’ve been eying is on sale in your size. (Also, I can’t tell you how many times a coworker has mentioned a killer sale to me because she knew that’d be something I’d be interested in. I mean, who, me, shop at work? Never.)
6. Test-drive trends at fast-fashion outlets before committing. Forever 21, H&M, and Missguided are great because you basically get to test-drive a trend before committing major bucks to any one piece. It’s a lot easier to just add one piece here and there to an otherwise reliable wardrobe, and one $13 peplum blouse or crazy-chunky collar necklace isn’t, in the long run, as important an investment as the pants you pair it with.
7. Learn your measurements.
Learn to buy what fits you in the here and now. Not the body you had in high school. Not the body you’re going to have after hitting up bootcamp eight times a week and only drinking a concoction of kale and sadness. Not the body that magazines are saying, with clever angles and photoshop galore, that you “should” have. Focus on the body you have right now.
8. (And remember that if something bunches or buckles, it’s going to look cheap, no matter how much money you spent on it.) If I had every dollar back for all the jeans and dresses I’ve bought half a size too small with the hopes of one day fitting into them, I’d have considerably more money in my bank account right now. (Really, who does this and actually achieves that goal? And what kind of witchcraft are you practicing? I have a few pairs of J.Brands I would love for you to work that sorcery on, thanks.)
9. Remember the little details.
You don’t necessarily have to do a full-on Mad Men chignon (especially if you’re going for that French-chic bedhead look that literally no one except French models can get just right) or slap on a full face of pancake, contouring et al, but putting that much more effort towards your total look is often what separates something someone clearly slapped together to what you just, you know, threw together like any old thing (which is a statement best said while waving one perfectly manicured hand like the flawless style icon you are.)
10. If you love something, let it go. If it comes back, it was yours all along. It’s a loved-up adage about soul mates, but if you really love something that’s a shade more than you were willing to pay, make a mental note of it and walk away for at least 24 hours. If you can’t get it out of your head, and it fixates on you like no other, go back for it. If it’s still there, do a sartorial little “it’s meant to be” dance. If it’s not, don’t worry — there’s going to be something else out there that will complete your wardrobe just as much. (This also counts for online shopping. Fill up your cart all you want, but X out of your browser before you put your credit card information in. You can always go back later if that one shirt is haunting your dreams.)
11. Leave your credit card at home.
This forces you to do the once-around first, so you can really weigh what your options are before you commit and suddenly suffer a wicked case of buyer’s remorse. If you really, really love something and are afraid that it’s not going to be there when you go back after 24 hours, ask an associate if they’ll hold it for you, and call with the credit card number once you get home.
12. Consignment and thrift shops are goldmines. Really — it’s best to get over the fear of wearing something somebody else wore, because you’re missing out if you let that keep you away from major steals. These are the most awesome places in the history of ever, for endless reasons. They typically have pretty decent standards in regards to the wear and use of items they purchase and resell; you’ll be able to find things that might be a few seasons old but which you still have your heart set on; you get to examine the items in person rather than hedging all of your bets on Ebay; and a lot of thrift stores also do really great charity work in order to pay it forward. (Housing Works especially is absurdly good for this.)
60% off retail is still a sizable chunk of cash for a pair of shoes, but these babies have held up through years of parties and interviews and date nights and everything in between.
13. Make an effort to keep things in good condition — it’s way cheaper than replacing them entirely. Patching the lining of a jacket you really love, replacing the heels of your shoes when they get worn down, and even taking your bag in to get treated and spot-cleaned might seem like nuisances for the time being, but in the long run, you’ll save way more than if you just keep replacing them with things you might not love as much. This goes double for getting things hemmed and tailored in the first place — and if something says you ought to get it dry-cleaned, it’s in your best interest that you do just that.
14. Ask someone who works at the shop what she thinks you’d look good in. It’ll get you to try new things you might not otherwise try — really, as much as you might suspect that someone’s trying to jack up their commission, trust that their job is to help you find what you like best.
15. Vary colors or textures. All-black looks really, really good when you have a variety of textures throughout the outfit. (A knit sweater, denim jeans, leather boots, you get it.) The same principle goes for different shades of camel or gray, or whatever.
16. Look for alternatives. Shopstyle and Polyvore are great tools for doing this, because they basically sift through every option possible, but also just ask friends what they like best. I tell everyone I know about the skinny pants from J.Crew and Zara — they’re almost identical, and each have their devotees, but I mean, $35 for a pair of pants!
17. Make sure you’re comfortable, no matter what you’re wearing. Really. The aim of the game is all about how you carry yourself. What you wear might be a form of self-expression, but even the most money dress is going to fall flat if you keep fidgeting in it all night long. Own it. If you set your mind to the idea that you feel like a million bucks, whatever you’ve got on, then chances are good that you’re going to look it. 
