Olive green on deep, cool skin tones (Deep Winter)

The answer

No. Olive green sits well outside the Deep Winter palette. The nearest thing in the palette is #1E4A3E, ΔE 22.4 away. Under 12 reads as the same colour family; past 25 the two are visibly different colours.

It does not collide with anything on the season's avoid list, so the only question is distance.

How olive green scores across all twelve seasons

Olive green is an opinionated colour: True Autumn scores it 87 and Light Summer scores it 12. A gap that wide means the colour genuinely decides something, and getting it right is worth the effort.

Deep Winter sits 9 of twelve at 44, 42 points behind True Autumn. That gap is the honest size of the compromise, not a verdict on the colour.

• True Autumn: 87 (ΔE 5.4).
• Deep Autumn: 80 (ΔE 8.1).
• Soft Autumn: 68 (ΔE 12.7).
• Deep Winter: 44 (ΔE 22.4) <- this season.
• Light Summer: 12 (ΔE 27.8).

What to wear instead

Nearest first. These are the colours in the Deep Winter palette that get closest to what you wanted from olive green, so the substitution costs the least.

• #1E4A3E: deep, a forest green (ΔE 5.0).
• #0E3B32: very deep, a forest green (ΔE 6.1).
• #3E4148: deep, a charcoal (ΔE 3.3).