Oakley Software: the Apparel Line, Piece by Piece
More than a hundred Oakley Software pieces photographed in the studio: the line, its graphics, the waffle polos, beanies and what to check before buying.
Contents
One hundred and thirteen Software pieces have passed through this studio. It is the largest single line we have handled, more than twice as many items as any frame, and everything below comes from garments we have had in hand.
What it is
Software was Oakley's apparel and equipment line, not a frame. It shared the eyewear's language: the Icon ellipse, the Static O, the vertical spell-out, the Factory Pilot lettering. We have no primary source for the year the line started, so we do not give one. Oakley's own filings do record how its apparel grew in those years: 132 apparel styles released in 20001, 186 in 20012 and 413 in 20023.
Of the 113 pieces we have catalogued, 64 are dated to the 1990s in their listings and 29 to the 2000s; the remaining 20 carry no usable date. The 1990s pieces are the technical ones. The 2000s pieces move towards casual sportswear, waffle polos, chinos and hoodies, and are easier to find.
What we have actually had
Tops, 63 of the 113
35 tees, 16 polos, plus long-sleeve shirts, crewnecks, a sleeveless V-neck and embroidered sweaters. Waffle-knit polos recur more than any other single garment: centre-icon, panelled, quarter-zip and long-sleeve versions, in black, cream, beige and forest green.
Outerwear, 19
Hardshell waterproof jackets, including a seven-pocket version; technical ski jackets; kangaroo and panelled pullovers; Harrington cuts in waterproof and anthracite; a two-in-one panel ski jacket; dual-zip technical pullovers.
Bottoms, 19
Ski pants in cream, grey, black and forest green; cargo and technical shorts; casual chinos; icon trunks; women's biker shorts.
Accessories and footwear, 12
Icon and adjustable caps, a Static Icon beanie, sherpa trapper hats, a Static O technical backpack, a side bag, a sunglasses cleaning set, Teeth low boots.
Graphics we have seen on them
- Icon ellipse, 25 pieces
- Spell-out, 9, in vertical, flame, red and embroidered versions
- Static O, 3
- Factory Pilot, 2, one of them a sketch print
- One giant skull
- One-offs: Bomb, Mad Science, Mortar, Bob Head, Torpedo, Cyber, Green Flower, Sketch Icon
Oakley Software waffle polos
Sixteen polos with Software in the listing title have passed through the studio: ten dated to the 1990s, five to the 2000s and one with no date. Five are listed as waffle knit: three from the 1990s and two from the 2000s.
- 90's oakley software polo - XL · Sold
- 90's Oakley software long sleeve polo - S (M) · Sold
- 90's Oakley software polo - M · Sold
- 90's Oakley Software Quarter Zip Embroidered Polo · Sold
- 90's Oakley Software Panelled Polo · Sold
- 90's Oakley Software Icon Polo · Sold
- 90's Oakley Software Waffle Center Icon Polo (Size M, 68cm) · Sold
- 90's Oakley Software Waffle Center Icon Polo (Size M, 67cm) · Sold
- 90's Oakley Software Waffle Center Icon Polo (Size XL) · Sold
- 90's Oakley Software Metal Icon Polo · Sold
- Oakley Software Beige Embroidered Icon Polo · Sold
- 2000's Oakley Software Cream Waffle Polo (XL) · Sold
- 2000's Oakley Software Black Waffle Polo (M) · Sold
- 2000's Oakley Software Forest Green Icon Polo (L) · Sold
- Early 2000's Oakley Software Contrast Panel Polo Yellow / Slate (L) · Sold
- Early 2000's Oakley Software Quarter Zip Polo (L) · Sold
Vintage Oakley beanies
Nine Oakley beanies have passed through the studio: two dated to the 1990s in their listings, one of them a Software Static Icon; three from the 2000s; one 2023 Piet x Oakley collaboration; and three with no date.
- Vintage Oakley beanie - one size · Sold
- Vintage Oakley beanie (style 2) - one size · Sold
- Vintage Oakley beanie · Sold
- 90's Oakley beanie · Sold
- 90's Oakley Software Static Icon Beanie · Sold
- 00's Oakley icon beanie · Sold
- 00's Oakley Beanie · Sold
- 00's Oakley Expandable Beanie · Sold
- 2023 Piet x Oakley Scatter Skull Black Beanie · Sold
Alongside them, six winter hats with ear flaps: three from the 1990s (a Software Icon Moscow hat, an earflap hat and a Software sherpa trapper), two from the 2000s (an ushanka and a skull-patch sherpa trapper) and one undated sherpa earflap hat.
- 90's Oakley Software Icon Moscow Hat · Sold
- 90's Oakley Earflap Hat · Sold
- 90's Oakley Software Sherpa Trapper Hat Black / Grey (OS) · Sold
- Rare early 2000's Oakley ushanka hat · Sold
- 00's Oakley Skull Patch Sherpa Trapper Hat Charcoal (OS) · Sold
- Oakley Sherpa Earflap Hat · Sold
Factory Pilot graphics and gloves
Four Factory Pilot pieces have passed through the studio: a Software tee dated to the 1990s, a Software sketch-print tee from the early 2000s, an undated comic-style long-sleeve tee and an undated pair of Factory Pilot 2.0 gloves. The only other Oakley gloves we have had were a pair of leather moto gloves.
- 90's Oakley software Factory Pilot tee - L · Sold
- Early 2000's Oakley Software Factory Pilot Sketch Tee (M) · Sold
- Oakley vintage factory pilot comic style long sleeve tee - L · Sold
- Oakley Factory Pilot 2.0 Gloves · Sold
What to check before you buy one
- Screen prints. Prints from the 1990s crack along the fold lines before the cotton goes. Look at the ellipse, not at the shoulders.
- Waffle polos. They lose their shape at the collar first.
- Hardshell jackets. These are the ones to inspect properly: the laminate delaminates from the inside and it will not show from the face of the fabric.
- Ski pants. At this age the fabric is usually intact and the hems are worn.
Pieces we have had
These are the 113 pieces with Software in their listing title, grouped by the decade written in that title. Sold pieces stay here as a record; each photograph links to its original listing.
Dated to the 1990s in the listing, 64
Dated to the 2000s in the listing, 29
No date in the listing, 20
Sizing
Sizing runs small by current standards, and Oakley's own sizing shifted between the 1990s and the 2000s runs. We give flat measurements in centimetres on every listing rather than relying on the tag.
In the studio now
Related pieces listed today. Each one leaves this list the moment it sells.
-
Deadstock Oakley 2000's Metal Icon Visor Caps
€24,80Regular price €31 Sale price €24,80 -
00's Oakley Icon Buckle Leather Belt Black
€52Regular price Sale price €52 -
2000's Oakley Women's Zip Fleece Jacket (XL)
€68Regular price Sale price €68 -
Early 2000's Oakley Skull Print Short Sleeve Shirt (XL)
€80Regular price Sale price €80
Where to see them
Software pieces are in the sold archive with their dates and measurements. Whatever is currently available is in New arrivals.
If you are after a specific Software piece, write to us and we will look for it. That is what Sourcing is.
Sources
- Oakley, Inc. Form 10-K for the fiscal year ended 31 December 2000, filed with the US Securities and Exchange Commission. Item 1, Business: eyewear products table (date introduced, US suggested retail price), eyewear and apparel text; Item 7. www.sec.gov Consulted 30 Sep 2026.
- Oakley, Inc. Form 10-K405 for the fiscal year ended 31 December 2001, filed with the US Securities and Exchange Commission on 1 April 2002. Item 1, Business: eyewear products table; apparel. www.sec.gov Consulted 30 Sep 2026.
- Oakley, Inc. Form 10-K for the fiscal year ended 31 December 2002, filed with the US Securities and Exchange Commission on 31 March 2003. Item 1, Business: eyewear products table (Jackets and Wires); apparel. www.sec.gov Consulted 30 Sep 2026.
Counts, colourways and the years in our listings come from pieces photographed in hand in the studio. Dates of introduction come only from the sources above.
Written in Barcelona at 16.88studio, an archive and resale project working with technical and branded sportswear from the late 1990s and early 2000s. Corrections with a source are welcome: write to us.