Before the wardrobe switches entirely to tanks and shorts, there’s always that last week of May when you reach for the same few pieces on repeat. Here are the ones I could not stop wearing this month.
Six years buying for a department store taught me one thing: bestsellers stay bestsellers because they actually work in real life. These made the cut for that reason, not because they were new.
The Denim
Agolde Parker Long Denim Shorts (size 25)
A 4-inch inseam with a slightly longer leg than most shorts on the market. Size up if you prefer extra room through the thigh.
Everlane Way-High Sailor Jean (size 25, hems cut)
Exceptional fit for a high-rise jean. I sized up one from my usual and hemmed them at home. Available in several washes.
Citizens of Humanity Miro Relaxed Jeans (size 23)
A relaxed silhouette with a subtle barrel shape through the leg. They run large, so size down. I cut the hems to my preferred length.
Everlane The Way-High Curve Jean (size 26)
The curve jeans have an exaggerated rise and generous room through the hip. I went up two sizes for comfort and hemmed them myself.
Tops & Dresses
Quince Organic Cotton Boyfriend Crew Sweater (size small)
Fits true to size, but I prefer a little extra room with this one. It comes in multiple colors and the quality is impressive for the price point.
Astr The Label Bow Back Dress (size xs)
Comfortable enough for all-day wear. Hits full length on my 5-foot frame. Available in additional colors.
Amazon Linen Bow Tank (size small)
A roomy linen tank that feels soft from the first wash. I sized to small and it has a relaxed drape without looking sloppy.
J.Crew Relaxed Premium-Weight Cropped T-shirt (size small)
I have strong opinions about white tees, and this one hits the right weight — substantial enough to look polished, light enough for layering. Comes in more colors.
Everlane Boatneck Tank (size xs)
Fitted through the torso with a flattering neckline. Size up if you want a looser fit.
The Carry
Amazon Canvas Tote
Solid size for everyday use, comes with a shoulder strap and multiple color options.
Style Math: A $68 jacket worn 40 times costs $1.70 per wear. The pieces above earned their place through repetition — not hype.
How do you decide what makes the monthly list?
I track what I actually reach for, not what I bought. If a piece survives three wears in two weeks without feeling like an effort, it stays on the rotation.
Your sizing runs small — should I size up across the board?
Not always. The Quince sweater and Everlane boatneck run true to size. The Citizens of Humanity jeans actually run large. I note the fit direction on each item above.
Do you hem your own jeans?
I do, whenever the rise fits but the length does not. It saves money and you get the exact break you want.
A note from Maya: I used to buy the trend first and ask questions later. Now I let a piece prove itself through a full month of wearing before deciding if it belongs in my closet.