1. You know how a lot of online stores have email lists you can subscribe to? Yeah, you should do that. Gmail now has a feature where it separates you emails into different types. When I'm in the mood to buy something, I'll scroll through my promotions folder and see if any of the stores that I like are offering special discounts. I regularly get coupon codes for 10, 15, or 20% off. Sometimes, when you subscribe, they'll ask for your birthday. It benefits them because they collect information about what demographic shops with them, and it benefits you because the ones that ask for it usually send you a birthday coupon.
2. Another way to learn about special offers and flash sales is to follow stores you like on social media. Some stores will use them for exclusive offers and discounts that they don't offer anywhere else.
3. Get familiar with sale cycles. Spring and summer clothing comes into stores around February, so that's when winter gear will be the cheapest; cold weather clothing comes in around September, so that's when you'll want to buy summer clothes.
3a. Of course, the corollary with that is to not buy anything too trendy. You may not be wearing it for a while, and you don't want people to literally look at you and think, "man, that's so last summer."
(If you only ever buy vintage clothing, the previous two tips maybe aren't as useful. However, I supplement my wardrobe pretty heavily with items from stores like Topshop, Zara, and Asos; they, and a lot of the other trend driven stores, frequently have items that have a vintage or retro feel to them, and it's well worth it to check them out. I particularly recommend checking out Asos.com. Their sale section is larger than their selection of full priced merchandise, they offer a lot of different styles at a lot of different price points, and they have free shipping with no minimum purchase.)
4. If there's a vintage store in your area, try to get in there regularly. My store in Chicago is Vintage Underground, and as I've mentioned before, I'm there often enough that they'll give me a little bit of a deal on things. Second-hand and vintage stores often have some leeway to negotiate, especially if you're a familiar face that they know they're going to see again. I might only spend $20 when I'm in there, but I'm a loyal enough shopper that it adds up.
I spend way too much time on Etsy, but my lost afternoons are your gain. In no particular order, here are some of my favorite shops.
1. Voyeur Vintage
Voyeur Vintage is a smaller store, but they have a great selection of apparel and accessories from the 50s and 60s. Clear photos and accurate measurements (a must if you're shopping for vintage online) make shopping her store easy.
Turquoise Plaid Skirt - $38
2. Bloomers and Frocks
Bloomers and Frocks has a wide range of clothing, accessories, and shoes, and she sorts her store by size, a feature that I always appreciate.
Red Chiffon Shirtdress - $58
3. My Vintage Hat Shop
My Vintage Hat Shop is, well, my vintage hat shop. They have a large selection of unique vintage hats sorted by era, and if you like them on Facebook, she regularly offers discounts.
Off White Straw Hat with Veil - $37
4. Vacation Vintage
Vacation Vintage is another smaller store, but I love their selection of dresses. They feature everything from the 40s through the 80s, but there's a curated feel to their collection that I like. Definitely follow them on social media for discounts.
50s Dusty Rose Party Dress - $82
5. Very Vintage Store
Very Vintage Store is a lovely store with highly curated merchandise. She seems to offer flash sales on a somewhat regular basis. The merchandise that I've ordered from the store has arrived promptly and in great shape.
Mediterranean Blue Maxi Dress - $61