I wish I was organized enough to plan out my shopping list in advance and stick to it, ignoring the barrage of online sales that flood my inbox and tempt me to spend on things I shouldn’t. I am not, but I aspire to be, and perhaps putting it on the interwebz will make me. Even though I may not be a methodical as purchasing a well-thought-out 15 pieces each month, I still love a good list and often spend subway rides home listing out the upgrades my wardrobe needs (especially as the NYC subway system is a wonderful place of style inspiration). When planning my start of season shopping list, I like to focus on pieces I know I’ll wear over and over again. I’ve realized that investing in a few dresses I’ll wear over and over again all season and not mind is worth the money and stress it relieves in the morning, even if by the end of the season, I’m so sick of them, I never want to wear them again. It’s that whole math principal that is actually a really smart way to buy (promise to blog more about it soon — it will seriously change your life). But the idea is to divide the cost of an item by number of times you wear it to get a good idea of the return on your investment, and I find each season that a few key pieces, which almost always includes a couple pairs of shoes, a couple work-friendly dresses I am so obsessed with (judged by how long I’ve been lusting after them waiting for them to go on sale), a top or two, and a skirt or pair of pants, a jacket, one investment piece I know I’ll wear forever (which could be anything from a stripe shirt to a classic work tote to a pair of goes-with-everything loubs), one fancier item, be it a dress, statement skirt or jumpsuit, that will cover me for engagement parties/weddings/etc. that season, and some trendy accessories is usually the perf formula to get me through the season with minimal stress. The trick is sticking to it, taking the hit at the beginning of the season until waiting too long to convince myself it’s something I need and not maximizing the amount of wear out of it, and of course, not falling victim to the endless temptation of other cute things I see online, on insta, or in my inbox. But in hopes for the new summer season and my new short short hair (Did I mention I did the Sienna Miller bob and chopped it all off? Sadly, I don’t feel like I look as cool and hot as Sienna and feel a bit regretful, but I digress…), I will be a new woman, or at least savvier smarter shopper. And as that new woman, here is what I’ll be investing in and wearing this month.
1. MAXI DRESS

DVF
DVF Two-Tone Jersey Wrap Maxi Dress, $299, theoutnet.com
2. EASY WORK DRESSES

TIBI
Tibi Satin Poplin Dress, $158, tibi.com

Cos

DVF
DVF Taffy Cotton Shirt Dress, $208.80, dvf.com

SUNO
Suno Embroidered Twill Mini Dress, $297, theoutnet.com
3. LACE TOP

DVF
DVF Brielle Lace Top, $134, dvf.com
4. CITY TO BEACH SHORTS

Helmut Lang
Helmut Lang Crepe Shorts, $100, theoutnet.com
5. SLEEVELESS VEST

IRIS AND INK
Iris and Ink Skye Cotton Vest, $195, theoutnet.com
6. COTTON TOP

HELMUT LANG
Helmut Lang Draped Wrap-Effect Crepe Top in white, $115.50, theoutnet.com
7. TIERED DRESS

TIBI
Tibi Laser-Cut Crepe Dress, $234.06, theoutnet.com
8. PEEP-TOE WEDGES

Vince
Vince Kostel Slingback Espadrilles Wedges, $297.50, Shopbop.com
9. ESPADRILLE WEDGES

VINCE
Vince Spencer Espadrille Wedges in grey and black, $295, shopbop.com
10. STACKED HEEL SANDALS

VINCE
Vince Freida Sandals, $297.50, shopbop.com
11. CROP TOP

ZARA
Flounce Sleeve Eyelet Crop Top, $39.90, zara.com
12. WRAP TOP

TIBI
Tibi Bibelot Wrap-Effect Crepe Top in white, $146, theoutnet.com
13. BUCKET BAG

IRIS AND INK
Iris and Ink Brixton Textured-Leather Shoulder Bag in white, $225, theoutnet.com

SCHUTZ
Schutz Cyby Tall Gladiator Sandals, $260, Shopbop.com
15. TASSLE EARRINGS

OSCAR DE LA RENTA
Oscar de la Renta Tassle Earrings in black and gold, $255, neimanmarcus.com
16. DRAPED PANTS

TIBI
17. CROPPED JUMPSUIT

TIBI
Tibi Agathe Strapless Jumpsuit, $486.50, tibi.com
18. SIMPLE BIKINI

COS

COS
Cos Textured Bikini Top $25 and Cos Textured Bikini Bottom $25, cosstores.com
19. GOLD CUFF

KENNETH JAY LANE
Kenneth Jay Lane Gold-Tone Thick Cuff, $70, theoutnet.com