I would use something fairly apolar if you're using silica as the stationary phase, maybe a 1:7 mixture of petroleum ether:ethyl acetate, I used that for an isoxazole with an amine and it worked well. If it doesn't work (you get a value of 0 or 1) play with the ratios, or use another solvent/solvent mixture. A very common starting point is hexane:ethyl acetate 1:1

The best way I go about it is to start with the solvents ratio of 1:1 and then optimise the solvent system accordingly. In most cases hexane: ethyl acetate doesn't disappoint. 

When you have a free amine group, esp. aliphatic, but even aromatic, it is better to use alumina as stationary phase for TLC and Column Chromatography. Silica is a polar, so the amine group can stick to it. This is especially important when you do a column because with silica, your compound may just stick to it and never elute out. 

With alumina, try 20% EthylAcetate/Hexanes. If your compound doesn't move up, increase EA%. It also depends on what substitutions you have on the aniline.

TLC was carried out by using silica gel G coated glass plate of 2 mm thickness using benzene and ethyl acetate (9:1; v/v) as the solvent. The visualization was carried out in an iodine chamber. 

In general, mixing an apolar solvent (hexanes, benzene, cyclohexane, petroleum ether) with a somewhat polar solvent (DCM, Ethyl acetate, n-butanol) works well with most compounds. Given your compound, the only precaution I can think off is avoiding acidic solvents and amines, I would simply use petroleum ether/hexane/benzene with ethyl acetate, seems like the safest bet.