In Review: The Timex Milano Men’s Dress Watch (& win it)

Timex Milano 38mm Leather Strap Watch – $99

Remember Mad Men? I know, wasn’t that long ago. But still. Everyone (in real life) started wearing skinny ties and slicking their hair back and randomly saying things like “the carousel“. It was all sorta… costumey. But the thing about retro style is that it can look 100% at home in the here and now, as long as you limit the influence of an era to one or two pieces in an entire outfit. And a watch, like this watch, is a perfect example of how great a little retro can look.

Brushed cushion case with polished accents.

Unlike a lot of other retro-influenced watches, this Timex Milano doesn’t rely on multiple elements to get across the idea that its design is based in the past. Again, more does not always = better. It’s the watch’s case. Cushion shaped, supporting a dead simple collection of indices, hands, and font. All quietly combining against a super subtle, barely noticeable sunburst texture on the dial, to look like something that Don guy mighta worn.

Subtle sunburst dial. It’s not lifeless, but it’s not glaring either.

But it’s still sized and constructed with the 21st century in mind. Quartz movement (keeps it cheap-ish). Quick change spring bars for easy strap swap outs (get a brown strap too and you’ve got a heck of a versatile dress watch). 50m of water resistance. And a 38mm case diameter which avoids the doll-like proportions of the Marlin. It should look great on just about anyone’s wrist. Timex calls it the “Milano XL 38mm”. I don’t know why. It’s not XL. Hardly. It’s just right.

Should be good with a suit. Or a sweater polo. Or lots of other things.

It’s not without flaws though. It does have the Timex “tick”. It’s not silent. In a (very) quiet room, if your focus drifts, it can very well land on the tick… tick… TICK of the seconds hand. Not all Timex watches have the “tick”. This one does. So those with sensitive ears might need to stick this thing in a drawer overnight, or risk being kept awake, edging closer and closer to madness with every rip of the seconds hand.

38mm case size and 20mm lugs. A perfect dress watch size for plenty.

Also, that leather band is super flimsy feeling. It’s soft all right, and the quick change pins on the spring bars are appreciated, but I feel like if I wanted to, I could go pure hulkamania and rip the thing in half. Also, there’s hardly any lume here. (Like, none maybe?) No indiglo, that’s for sure. But the sunburst dial is worth it. And for a relatively cheap dress watch, that’s not too surprising.

Quick change strap pins. Get an additional brown strap and you’re set.

It’s a stunner though. Another horse in the stable of recent Timex style wins. And it’s priced at a level that’s accessible to the majority of us. It does feel like one of those models that won’t be straying too far from Timex.com. Meaning, it might be a while (or never) until it trickles down to 3rd party websites, and thus, it’ll stick close to retail price until that happens. For now, full price or a random 20% off code might be as good as it gets.

Note: We had some early technical difficulties on the contesting front. Thanks for the patience, I think we should be good to go now. Good luck!

UPDATE II: Oh for crying out loud the CAPTCHA thingy is broken again. Sorry guys. We’re on it. Thanks for the patience. What a pain in the arse.

UPDATE III: NOBODY BLEEPIN’ MOVE (unless you want to enter to win the Timex, then by all means)… I think we figured it out.

Enter here to win the Timex Milano shown in the post above. One entry per person. Deadline for entry is 11:59 pm ET 4/29/20. 

UPDATE: Congrats to Gram S. who won the drawing for the Timex Milano!