Is it just us, or does scoring a great piece for a ridiculously affordable price also make you feel weirdly victorious? It’s that feeling of somehow cheating the system or being let in on an insider secret. It’s the reason why we always take the time to tell you about the latest sales from our favorite stores and sites—both online and IRL—and why we never hesitate to share our favorite places to find affordable items.
Today, though, we’re taking the guessing out of it to bring you our ultimate guide on which items to buy to maximize your savings while minimizing the time and research that goes into hunting down sales and clipping coupons. We devised this handy guide detailing the most opportune times to buy certain items. Not only will it make you feel like a delightfully savvy shopper, but you’ll also save a pretty penny too. Ahead, discover the best time to buy these 14 fashion items on sale.
January: Suits. Since January is considered a slow month for suit sales, retailers lower prices to boost business. Featured: Etro Crepe Blazer and Cropped Stretch-Crepe Straight-Leg Pants 
Shop the matching Remain Birger Christensen Tapered Pants ($230). 
February: Jewelry. Whether or not you have a special someone on Valentine’s Day, you can still make off like a bandit thanks to the jewelry promotions pegged to the holiday. Featured: Stella McCartney Gold-Tone Heart Pendant Necklace 
March: Luggage. Come spring, you’re likely to find suitcases on sale, making it a great time to snag a new carry-on. Featured:T. Anthony Medium Structured Suitcase 
April: Raincoats. Retailers take the phrase, “April showers bring May flowers” seriously by stocking up on raincoats, yet making sure they’re priced to move since there’s a limited time to get rid of them before sunny May rolls around. Featured: Valentino R.E.D. Clear Petunia Raincoat 
April/May: Thrift and Consignment. You have spring cleaning to credit for the influx of gems to be found at thrift and consignment stores during these two months. Featured: Tamara Mellon Leopard-Print Goat Bomber Jacket 
May: Athletic Apparel. Whether it’s because it’s finally warm enough to exercise outside or the impending arrival of beach season, you’ll find fitness gear at a generous discount. Featured: T By Alexander Wang Rainbow Cotton-Terry Sweatshirt and Rainbow Cotton-Terry Shorts 
Shop the matching Beyond Yoga Midi High Waist Leggings ($97). 
July/August: Summer Apparel. Sales on summer collections are in full swing during these months, making it the perfect time to pick up seasonal essentials such as sundresses, sandals, and shorts. Bonus tip: Sale stock will be more plentiful in July but come August, the discounts will be steeper. Featured: Marni Cropped Denim Top and Marc Jacobs Printed Wool-Twill Shorts 
August: Swimsuits. Stores want to clear out summer leftovers to make room for fall merchandise. Translation: The price on that bikini you’ve been stalking is likely to take a swan dive. Featured: Mara Hoffman Garlands Lace-Up Swimsuit 
September: Sunglasses. With Daylight Savings looming on the horizon, sunnies (priced at their highest during the summer months) get a tidy markdown. Featured: Sunday Somewhere Pearl Sunglasses in Mushroom 
October: Denim. After the back-to-school rush has died down, retailers cut prices, and jean stock tends to be at the top of their list. Featured: Acne Studios Roc Light Vintage 34” L Jeans 
November: Luxury Items. Since Black Friday and Cyber Monday promotions often feature store-wide sales, this is an ideal time to treat yourself to luxury items (such as like cashmere sweaters) that don’t often go on sale. Featured: Bottega Veneta Contrast-Trimmed Cashmere Top 
November: Pajamas. Retailers often put PJ sets on sale in late November in an attempt to convince shoppers to give the gift of loungewear. Featured: Equipment Lillian Polka-Dot Washed-Silk Pajama Set 
November: Sneakers. Incoming shipments of winter boots and shoes means sneaker prices will be seriously slashed. Featured: Asics Grandest High Top Sneakers 
December: Outerwear. With the winter season well underway, stores are looking to clear out their inventory to accommodate spring collections. That means a steep discount on that oversize coat you’ve been eyeing all season. Featured: Rochas Oversized Wool-Blend Coat 
Next, I Rebuilt My Entire Underwear Collection From Scratch–Here Are The Pairs I’m Buying.
This post was published at an earlier date and has since been updated.
Strategic shopping.
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