This outfit card is one of the most versatile out there as cheaper deeds are going to be useful for almost any style of play. In particular, it is a staple of the "Landslide" archetype of decks which rely on the strategy of buying up town instead of fighting out for it. Irving Patterson is a popular target for this ability.
The primary drawback of this outfit ability is the fact it requires you to boot your dude to that deed to get the discount potentially exposing them to shootouts they can't handle until the end of the day. Cards that mitigate this drawback are particularly good in combination with it!
Combos well with:
Out of Town Deeds (Blake Ranch/Jackson's Strike/The R&D Ranch) - The primary danger of using this outfit ability is that it leaves one of your influence bearing dudes booted and likely exposed for the opponent to call out. Using the outfit ability on an out of town deed keeps the dude you're using with the ability with safe as enemy dudes (without Shadow Walk/Mustang) need to boot over to get to them and can't call them out the first turn without some action cards shenanigans.
Clementine Lepp + Saloons (Charlie's Place/Pearly's Palace/Killer Bunnies Casino/The Union Casino) - Again this negates the primary drawback of exposing your dudes by using the outfit ability. Clementine simply cannot be called out if she's in a saloon you own! Using the ability while she's already in a saloon will grant you a 2-GR discount on subsequent deeds due to the influence bonus she receives.
Lillian Morgan + Shadow Walk - This is just an example. Any high influence dude with a movement ability like Mustang can work too though Shadow Walk is the most cost effective of them. You boot Lillian Morgan to make a free 5-cost deed, then you simply Shadow Walk back to the safety of home before she can be called out!
Make the Smart Choice - This card basically allows your exposed dude to run back home during the shootout plays step. If you have one of these in hand, you've got a risk free use of this outfit ability!