Introduction: Retrograde shear causes endothelial damage and is pro-atherogenic. The purpose of our study was to examine the impact of vascular remodeling from habitual exercise training on acute changes in retrograde shear and microvascular oxygenation (SMO2) induced via 30 min of external compression. Methods: Participants included 11 exercise trained (ET) men (Division I track athletes; age 20 ± 3 years) and 18 recreationally active (RA) men (age 23 ± 5 years). Near-infrared spectroscopy (NIRS) was used to measure vastus medialis SMO2. Doppler-ultrasound was used to assess SFA intima-media thickness, diameter and flow velocity to derive retrograde shear. Vascular measures were made at baseline (BASELINE), during a sham condition (calf compression to 5 mmHg, SHAM) and during the experimental condition (calf compression to 60 mmHg, EXP). Results: Compared to RA, ET had larger SFA diameters (0.66 ± 0.06 vs 0.58 ± 0.06 cm, p < 0.05) and lower SFA IMT (0.33 ± 0.03 vs 0.36 ± 0.07 mm, p < 0.05). Retrograde shear increased similarly in both groups during EXP (p < 0.05) but ET men had lower overall retrograde shear during the conditions (BASELINE 75.8 ± 26.8 vs EXP 88.2 ± 16.9 s−1) compared to RA men (BASELINE 84.4 ± 23.3 vs EXP 106.4 ± 19.6 s−1p < 0.05). There was a similar increase in SMO2 from BASELINE to SHAM (ET + 8.1 ± 4.8 vs RA + 6.4 ± 9.7%) and BASELINE to EXP (ET + 8.7 ± 6.4 vs RA + 7.1 ± 9.0%) in both groups. Conclusion: Beneficial vascular remodeling in ET men is associated with lower retrograde shear during external compression. Acute increases in retrograde shear with external compression do not detrimentally impact microvascular oxygenation.