In this article, we investigate the regulation of wind regime by windbreaks of different designs formed by thinning. In particular, we look at the effects of thinning in 52–67 years old oak stands. Based on our results, different windbreaks designs of foliage and aphyllous states influence wind regime of adjacent fields. This research shows that windbreaks of sieve-looking and blown designs with an average optical porosity of 20–25% between the trunks and 5–10% in the crowns have better aerodynamic properties than windbreaks of dense design. The uniformity coefficient of reduction in the airflow ranged between 0.42 and 0.76. There is a clear tendency to decrease wind velocity at a distance of 15H in the leeward side, which has a beneficial effect on agronomic productivity of the surrounding areas. With the transition of windbreaks from full foliage to aphyllous state the optical trunk porosity of plantations increases 1.8–3.0 times, and in crowns—2.5–4.0 times. The windbreaks of blown and sieve-looking designs in the aphyllous state with an average porosity between trunks of 40–50% and in the crowns of 20–30%, regulate more effectively the wind regime in comparison with windbreaks of dense design. According to our findings, the windbreaks of blown design with porosity 40–50% between the trunks and 0–10% in crowns and sieve-looking design have the best ameliorative properties in the region.