It varies by category. Trousers, including the Ojai Pant, fit close to a standard US size through the waist — sizing up rarely improves the fit and usually just adds volume to the leg. Knitwear is designed oversized, so the labeled size is less meaningful than the actual chest and length measurements. For outerwear, the fit is boxy by design and most people find their usual size works fine. When buying secondhand, request measurements rather than relying on the tagged size.

For outerwear and trousers, yes — the quality is closer to The Row than the secondhand pricing suggests. The Row has stronger resale demand, which drives prices up; Jenni Kayne doesn't carry that same market premium, so the gap between what you pay secondhand and what you get in terms of fabric and construction is favorable. Toteme is a reasonable comparison for basics and knitwear, and the two brands trade at similar secondhand prices. If the specific silhouette works for you, Jenni Kayne outerwear secondhand is often the better value.

Focus on three areas: pilling at the underarms and cuffs (common on wool-blend styles), the condition of the buttons and their attachment points (loose buttons are easy to fix but worth noting), and any signs of dry cleaning residue or slight color fading along the shoulders. Linen pieces can look more distressed than they are due to wrinkling — check whether creases are structural or just from being folded. Cashmere-blend styles show wear faster than pure wool versions, so be more selective with those.

Pre-2019 pieces are generally fine, but the brand refined its finishing and fabric selection noticeably around 2019 to 2020. Earlier pieces can feel slightly less polished in construction details. That said, the core silhouettes are similar, and for something like a chunky knit or a simple trouser, the difference is minor. For outerwear, the newer iterations are worth the slight premium if condition is comparable. The main reason to consider older pieces is price — they tend to list lower, and for casual basics, the quality gap is small enough to be worth it.